VINO / Gaucho Group Holdings, Inc. - SEC फाइलिंग, वार्षिक रिपोर्ट, प्रॉक्सी स्टेटमेंट

गौचो ग्रुप होल्डिंग्स, इंक.
US ˙ OTCPK

मूलभूत आँकड़े
LEI 549300OJQBEC14FI7W33
CIK 1559998
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Gaucho Group Holdings, Inc.
SEC Filings (Chronological Order)
यह पृष्ठ SEC फाइलिंग की एक पूरी, कालानुक्रमिक सूची प्रदान करता है, ओनरशिप फाइलिंग को छोड़कर, जो हम अन्यत्र प्रदान करते हैं।
August 28, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 26, 2025 Gaucho Group Holdings, Inc. (Exact name of registra

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 26, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41s

August 28, 2025 EX-99.1

EX-99.1

Exhibit 99.1

August 15, 2025 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: June 30, 2025 ☐ Transition Report on Form 10-K ☐ Tra

August 1, 2025 EX-99.1

VINO SYMBOL REINSTATED: GAUCHO HOLDINGS MARKS NEW CHAPTER POST-REORGANIZATION

Exhibit 99.1 VINO SYMBOL REINSTATED: GAUCHO HOLDINGS MARKS NEW CHAPTER POST-REORGANIZATION Company resumes trading under “VINO” amid Argentina’s economic stabilization and U.S. partnership momentum MIAMI, FL / July 31, 2025 / Gaucho Group Holdings, Inc. (OTC:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leath

August 1, 2025 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 31, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

July 30, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 30, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 30, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

July 30, 2025 EX-99.1

EX-99.1

Exhibit 99.1

July 21, 2025 EX-99.1

EX-99.1

Exhibit 99.1

July 21, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 18, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 18, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

July 18, 2025 EX-99.1

EX-99.1

Exhibit 99.1

July 18, 2025 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 15, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

June 20, 2025 EX-99.1

Gaucho Holdings Emerges from Chapter 11, Aligns with Argentina’s Economic Upswing and Investor Confidence

Exhibit 99.1 Gaucho Holdings Emerges from Chapter 11, Aligns with Argentina’s Economic Upswing and Investor Confidence Mortgage availability, foreign capital inflows and U.S. economic support reinforce Gaucho’s strategic timing. MIAMI, FL / June 16, 2025 / Gaucho Group Holdings, Inc. (OTC: VINOQ), a company that includes a growing collection of e-commerce platforms with a concentration on fine win

June 20, 2025 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Bankruptcy or Receivership, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 16, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 Lincoln

May 16, 2025 EX-99.1

EX-99.1

Exhibit 99.1

May 16, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 13, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 13, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st S

May 15, 2025 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: March 31, 2025 ☐ Transition Report on Form 10-K ☐ Tr

March 31, 2025 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Bankruptcy or Receivership, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: March 28, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 Lincol

March 31, 2025 NT 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☒ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: December 31, 2024 ☐ Transition Report on Form 10-K ☐

March 31, 2025 EX-99.1

GAUCHO ANNOUNCES COURT APPROVED SETTLEMENT AND TIMELINE TO EMERGE FROM CHAPTER 11

Exhibit 99.1 GAUCHO ANNOUNCES COURT APPROVED SETTLEMENT AND TIMELINE TO EMERGE FROM CHAPTER 11 Settlement Terms Approved; Company to Exit Chapter 11 on or Before June 2, 2025 MIAMI, FL / March 31, 2025 / Gaucho Group Holdings, Inc. (OTC:VINOQ), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessor

March 31, 2025 EX-10.1

EX-10.1

Exhibit 10.1

March 27, 2025 EX-99.1

Delisting of Securities of Gaucho Group Holdings, Inc. from The Nasdaq Stock Market

Exhibit 99.1 Delisting of Securities of Gaucho Group Holdings, Inc. from The Nasdaq Stock Market NEW YORK, March 26, 2025— The Nasdaq Stock Market announced today that it will delist the common stock of Gaucho Group Holdings, Inc. Gaucho Group Holdings, Inc.’s stock was suspended on November 22, 2024 and has not traded on Nasdaq since that time. Nasdaq will file a Form 25 with the Securities and E

March 27, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: March 26, 2025 Gaucho Group Holdings, Inc. (Exact name of registran

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: March 26, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 Lincol

March 18, 2025 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: March 18, 2025 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

March 18, 2025 EX-99.1

Dear Stockholders,

Exhibit 99.1 Dear Stockholders, We’re excited to provide you with an important update regarding the status of our Chapter 11 reorganization process. On March 12, 2025, Gaucho Holdings entered into a settlement term sheet that we believe represents a constructive resolution to the ongoing proceedings. If approved by the Chapter 11 Bankruptcy Court, this settlement is expected to lead to our structu

March 14, 2025 8-K

Bankruptcy or Receivership

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: March 12, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 Lincol

February 12, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 ☐ TRANSITION REPORT UNDER S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to . Commission file number: 001-40075 Gaucho Group Holdin

February 12, 2025 EX-10.14

Letter Agreement and Master Promissory Note dated January 31, 2025*

Exhibit 10.14 ARGENTINA STRATEGIC OPPORTUNITY FUND LLC December [], 2024 Gaucho Group Holdings, Inc. 1111 Lincoln Road, Suite 500 Miami Beach, FL 33139 Re: Line of Credit Ladies and Gentlemen: Argentina Strategic Opportunity Fund LLC (the “Lender”) is pleased to confirm that it holds available to Gaucho Group Holdings, Inc. (the “Borrower”) a $1,500,000.00 line of credit (as such line of credit ma

December 18, 2024 8-K

Unregistered Sales of Equity Securities

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 18, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State Commission IRS Employer of Incorporation File Number Identification No. 1111 Lin

November 27, 2024 EX-99.1

GAUCHO GROUP HOLDINGS, INC. PROVIDES UPDATE ON QUARTERLY REPORT FILING

Exhibit 99.1 GAUCHO GROUP HOLDINGS, INC. PROVIDES UPDATE ON QUARTERLY REPORT FILING MIAMI, FL / November 27, 2024 / Gaucho Group Holdings, Inc. (OTC:VINOQ), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (the “Company” or “Gaucho Holdings”), today provided an update to the timing of fili

November 27, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 27, 2024 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 27, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 Lin

November 14, 2024 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: September 30, 2024 ☐ Transition Report on Form 10-K

November 14, 2024 SC 13G/A

VINO / Gaucho Group Holdings, Inc. / 3i, LP - SC 13G/A Passive Investment

SC 13G/A 1 g084553sch13ga.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* Gaucho Group Holdings, Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 36809R503 (CUSIP Number) September 30, 2024 (Date of Event which Requires Filing of this Statement) Check the a

November 13, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 13, 2024 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 13, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 Lin

November 13, 2024 EX-99.1

Stockholder update dated November 13, 2024

Exhibit 99.1

November 13, 2024 8-K/A

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 12, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 L

November 13, 2024 EX-99.1

GAUCHO HOLDINGS INITIATES CHAPTER 11 REORGANIZATION TO PROTECT CORE ASSETS

Exhibit 99.1 GAUCHO HOLDINGS INITIATES CHAPTER 11 REORGANIZATION TO PROTECT CORE ASSETS Strategic Filing Aims to Protect Operational Continuity for the Benefit of Stockholders MIAMI, FL / November 13, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and ac

November 12, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 12, 2024 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 12, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 Lin

November 12, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 7, 2024 Gaucho Group Holdings, Inc. (Exact name of registr

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 7, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 1111 Linc

November 12, 2024 EX-99.1

GAUCHO HOLDINGS REPORTS STRONG SALES GROWTH AND INCREASED PRICING POWER IN ARGENTINE WINE MARKET

Exhibit 99.1 GAUCHO HOLDINGS REPORTS STRONG SALES GROWTH AND INCREASED PRICING POWER IN ARGENTINE WINE MARKET YTD Sales Soar 185% With a Significant 40% Increase in Average Sales Price Source: Gaucho Group Holdings, Inc. 11.07.2024 MIAMI, FL / November 07, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on

November 12, 2024 EX-99.1

November 12, 2024

Exhibit 99.1 November 12, 2024 Dear Stockholders, As you may know, Gaucho Group Holdings, Inc. (the “Company”) has been embroiled in federal and state court litigation where we have been fighting back against a toxic dilution funder that has attempted to divest our great company of its assets, including our prized Algodon Mansion and Algodon Wine Estates in Argentina. While we have diligently pros

November 1, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 30, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

November 1, 2024 EX-99.1

Stockholder update dated October 30, 2024

Exhibit 99.1

October 8, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 8, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41s

October 8, 2024 EX-99.1

REVITALIZATION OF ARGENTINA’S PROPERTY MARKET: GAUCHO HOLDINGS FORECASTS A NEW ERA IN LUXURY REAL ESTATE

Exhibit 99.1 REVITALIZATION OF ARGENTINA’S PROPERTY MARKET: GAUCHO HOLDINGS FORECASTS A NEW ERA IN LUXURY REAL ESTATE Record Sales and Successful Tax Amnesty Propel Growth in Argentina’s Luxury Real Estate MIAMI, FL / October 8, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real esta

October 8, 2024 EX-99.2

Stockholder update dated October 8, 2024

Exhibit 99.2

September 25, 2024 EX-99.2

GAUCHO HOLDINGS’ ALGODON FINE WINES EXPANDS U.S. DISTRIBUTION NETWORK WITH GIANNONE WINE & LIQUOR CO

Exhibit 99.2 GAUCHO HOLDINGS’ ALGODON FINE WINES EXPANDS U.S. DISTRIBUTION NETWORK WITH GIANNONE WINE & LIQUOR CO New Partnership Enhances Presence of Gaucho Holdings’ Wine Brand in Key Markets MIAMI, FL / September 25, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and l

September 25, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 24, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE

September 25, 2024 EX-99.1

Stockholder update and press release dated September 24, 2024

Exhibit 99.1

September 16, 2024 EX-99.2

Update to stockholders dated September 16, 2024

Exhibit 99.2

September 16, 2024 8-K/A

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 16, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 N

September 16, 2024 EX-99.1

GAUCHO HOLDINGS OPTIMIZES COSTS AMIDST ARGENTINE ECONOMIC OVERHAUL

Exhibit 99.1 GAUCHO HOLDINGS OPTIMIZES COSTS AMIDST ARGENTINE ECONOMIC OVERHAUL Projected $1.6 Million in Savings as Company Leverages Argentine Economic Reforms MIAMI, FL / September 16, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (th

September 16, 2024 EX-99.1

GAUCHO HOLDINGS OPTIMIZES COSTS AMIDST ARGENTINE ECONOMIC OVERHAUL

Exhibit 99.1 GAUCHO HOLDINGS OPTIMIZES COSTS AMIDST ARGENTINE ECONOMIC OVERHAUL Projected $1.6 Million in Savings as Company Leverages Argentine Economic Reforms MIAMI, FL / September 16, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (th

September 16, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 16, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE

August 29, 2024 EX-99.1

Stockholder update dated August 28, 2024

Exhibit 99.1

August 29, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 28, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41s

August 22, 2024 8-K

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 20, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41s

August 22, 2024 EX-99.1

GAUCHO GROUP HOLDINGS, INC. STRENGTHENS LEADERSHIP WITH APPOINTMENT OF DAVID REINECKE TO BOARD OF DIRECTORS

Exhibit 99.1 GAUCHO GROUP HOLDINGS, INC. STRENGTHENS LEADERSHIP WITH APPOINTMENT OF DAVID REINECKE TO BOARD OF DIRECTORS Strategic Appointment Underscores Commitment to Leveraging New Opportunities in Argentina’s Evolving Market Landscape MIAMI, FL / August 22, 2024 / Gaucho Group Holdings, Inc. (NASDAQ: VINO), a company that includes a growing collection of e-commerce platforms with a concentrati

August 21, 2024 EX-4.1

Amendment to the Company’s 2018 Equity Incentive Plan (21)

Exhibit 4.1 AMENDMENT NO. 5 TO THE GAUCHO GROUP HOLDINGS, INC. (FORMERLY ALGODON WINES & LUXURY DEVELOPMENT GROUP, INC.) 2018 AWLD EQUITY INCENTIVE PLAN Section 4(a) of the Plan, as previously amended, is hereby further amended as follows: Section 4. Shares Available for Awards (a) Shares Available. Subject to adjustment as provided in Section 4(c) of the Plan, the aggregate number of Shares that

August 21, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 16, 2024 Gaucho Group Holdings, Inc. (Exact name of registra

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 16, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41s

August 16, 2024 EX-99.2

Argentina Could Lead Global Returns in 5 Years, According to Explorador Capital

Exhibit 99.2 Argentina Could Lead Global Returns in 5 Years, According to Explorador Capital Andrew Cummins, founder of Explorador Capital, stated in an interview with Bloomberg Línea that the country’s bonds and stocks could stand out on a global scale Argentina Could Lead Global Returns in 5 Years, According to Explorador Capital By Francisco Aldaya August 15, 2024 | 05:00 AM Buenos Aires — Expl

August 16, 2024 EX-99.1

Stockholder update dated August 16, 2024

Exhibit 99.1

August 16, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 16, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41s

August 14, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 ☐ TRANSITION REPORT UNDER SECTIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to . Commission file number: 001-40075 Gaucho Group Holdings, I

August 1, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 31, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

August 1, 2024 EX-99.1

Stockholder update dated July 31, 2024

Exhibit 99.1

August 1, 2024 EX-99.2

Benzinga article

Exhibit 99.2

July 12, 2024 EX-99.1

July 11, 2024 Investor Presentation

Exhibit 99.1

July 12, 2024 8-K

Regulation FD Disclosure, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 11, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

July 9, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definitive Proxy Statement ☒ Definitive Additional Material ☐ Solicitation Mat

July 3, 2024 EX-99.1

GAUCHO GROUP HOLDINGS, INC. TO HOST EXCLUSIVE SHAREHOLDER EVENT ON JULY 11 AT NASDAQ MARKETSITE IN NEW YORK CITY

Exhibit 99.1 GAUCHO GROUP HOLDINGS, INC. TO HOST EXCLUSIVE SHAREHOLDER EVENT ON JULY 11 AT NASDAQ MARKETSITE IN NEW YORK CITY Event to Feature Insights into Expansion Plans and Initiatives for 2024 and Beyond MIAMI, FL / July 3, 2024 / Gaucho Group Holdings, Inc. (NASDAQ: VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real est

July 3, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 3, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 3, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st S

July 1, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 1, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st S

July 1, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☒ Definitive Proxy Statement ☐ Definitive Additional Material ☐ Solicitation Material under §240.

July 1, 2024 EX-99.1

GAUCHO HOLDINGS ENGAGES RENOWNED ARCHITECT GERHARD HEUSCH TO LEAD RENOVATIONS AT ALGODON MANSION

Exhibit 99.1 GAUCHO HOLDINGS ENGAGES RENOWNED ARCHITECT GERHARD HEUSCH TO LEAD RENOVATIONS AT ALGODON MANSION Enhancements Include Addition of Showroom and Sales Office for Algodon’s Vineyard Real Estate Project MIAMI, FL / July 1, 2024 / Gaucho Group Holdings, Inc. (NASDAQ), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate

June 26, 2024 PRER14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1) Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definitive Proxy Statement ☐ Definitive Additional Material ☐ Solicitation Ma

June 21, 2024 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definitive Proxy Statement ☐ Definitive Additional Material ☐ Solicitation Material under §240.

June 17, 2024 8-K

Regulation FD Disclosure, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 7, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st S

May 30, 2024 EX-99.1

Press release dated May 30, 2024

Exhibit 99.1

May 30, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 30, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st S

May 22, 2024 EX-3.1

Certificate of Designation of Senior Convertible Preferred Stock, dated May 21, 2024

Exhibit 3.1 CERTIFICATE OF DESIGNATION OF SENIOR CONVERTIBLE PREFERRED STOCK OF gaucho group holdings, INC. PURSUANT TO SECTION 151 OF THE DELAWARE GENERAL CORPORATION LAW Gaucho Group Holdings, Inc., a corporation organized and existing under the General Corporation Law of the State of Delaware (hereinafter called the “Corporation”), DOES HEREBY CERTIFY: That pursuant to resolutions adopted by un

May 22, 2024 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 21, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State Commission IRS Employer of Incorporation File Number Identification No. 112 NE 41st S

May 21, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 21, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 21, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State Commission IRS Employer of Incorporation File Number Identification No. 112 NE 41st S

May 20, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 ☐ TRANSITION REPORT UNDER SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to . Commission file number: 001-40075 Gaucho Group Holdings,

May 15, 2024 EX-99.2

Letter to stockholders dated May 15, 2024

Exhibit 99.2

May 15, 2024 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: March 31, 2024 ☐ Transition Report on Form 10-K ☐ Tr

May 15, 2024 EX-99.1

GAUCHO HOLDINGS ACHIEVES KEY NASDAQ MILESTONE

Exhibit 99.1 GAUCHO HOLDINGS ACHIEVES KEY NASDAQ MILESTONE Company Leverages Argentina’s Favorable Investment Climate to Expand Luxury Real Estate Portfolio MIAMI, FL / May 15, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (the “Company”

May 15, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 15, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st S

May 1, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 1, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant a

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 1, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st St

May 1, 2024 EX-99.1

GAUCHO GROUP HOLDINGS ANNOUNCES COMPLETION OF REVERSE STOCK SPLIT

Exhibit 99.1 GAUCHO GROUP HOLDINGS ANNOUNCES COMPLETION OF REVERSE STOCK SPLIT Strategic Move Aims to Enhance Stock Marketability and Attract Institutional Investment MIAMI, FL / May 1, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (the

May 1, 2024 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 1, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st St

April 30, 2024 EX-99.1

Algodon Wine Estates Property Map*

Exhibit 99.1

April 30, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K (Mark one) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Fiscal Year Ended December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40075 Gaucho Group Hold

April 30, 2024 EX-4.19

Description of Capital Stock of the Company*

Exhibit 4.19 DESCRIPTION OF OUR SECURITIES The following description summarizes important terms of our capital stock and our other securities. For a complete description, you should refer to our Certificate of Incorporation and bylaws, forms of which are incorporated by reference to this annual report, as well as the relevant portions of the Delaware General Corporation Law (“DGCL”). Capital Stock

April 30, 2024 EX-97.1

Clawback Policy for the Recovery of Erroneously Awarded Compensation*

Exhibit 97.1 GAUCHO Group HOLDINGS, Inc. Clawback Policy for the REcovery of Erroneously Awarded Compensation Adopted by the Board of Directors on November 27, 2023 Effective December 1, 2023 Purpose In accordance with the applicable rules of The Nasdaq Stock Market (the “Nasdaq Rules”), and Section 10D and Rule 10D-1 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), the Boa

April 29, 2024 EX-3.1

Amended and Restated Certificate of Incorporation filed with the Delaware Secretary of State effective May 1, 2024(23)

Exhibit 3.1

April 29, 2024 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: April 24, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

April 29, 2024 EX-99.1

GAUCHO GROUP HOLDINGS, INC. ANNOUNCES REVERSE STOCK SPLIT

Exhibit 99.1 GAUCHO GROUP HOLDINGS, INC. ANNOUNCES REVERSE STOCK SPLIT VINO common stock expected to begin trading on a split-adjusted basis on May 1, 2024 MIAMI, FL / APRIL 29, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (the “Company

April 24, 2024 8-K

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: April 18, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

April 24, 2024 EX-99.1

ARGENTINA’S NATO BID MAY PAVE THE WAY FOR ECONOMIC GROWTH, WITH POTENTIAL ADVANTAGES FOR GAUCHO GROUP HOLDINGS, INC.

Exhibit 99.1 ARGENTINA’S NATO BID MAY PAVE THE WAY FOR ECONOMIC GROWTH, WITH POTENTIAL ADVANTAGES FOR GAUCHO GROUP HOLDINGS, INC. Company Anticipates Stability and Growth to Positively Impact Real Estate Sector MIAMI, FL / April 22, 2024 Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real es

April 24, 2024 EX-99.2

GAUCHO GROUP HOLDINGS receives notice from Nasdaq REGARDING CONTINUED LISTING REQUIREMENTS

Exhibit 99.2 For Immediate Release GAUCHO GROUP HOLDINGS receives notice from Nasdaq REGARDING CONTINUED LISTING REQUIREMENTS MIAMI, FL / April 24, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (the “Company” or “Gaucho Holdings”), today

April 22, 2024 8-K

Unregistered Sales of Equity Securities, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: April 11, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

April 22, 2024 EX-99.1

GAUCHO GROUP HOLDINGS RESPONDS TO POSITIVE ECONOMIC SHIFTS IN ARGENTINA

Exhibit 99.1 GAUCHO GROUP HOLDINGS RESPONDS TO POSITIVE ECONOMIC SHIFTS IN ARGENTINA Leadership Discusses the Impact of Improved Financial Conditions on Real Estate Operations MIAMI, FL / April 19, 2024 / Gaucho Group Holdings, Inc. (NASDAQ: VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and acce

April 17, 2024 EX-99.1

GAUCHO GROUP HOLDINGS ANNOUNCES DELAY IN ANNUAL REPORT FILING

Exhibit 99.1 GAUCHO GROUP HOLDINGS ANNOUNCES DELAY IN ANNUAL REPORT FILING MIAMI, FL / April 16, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (the “Company” or “Gaucho Holdings”), today announced that the Company and its auditors are co

April 17, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: April 16, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

April 10, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: April 9, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

April 10, 2024 EX-99.1

Press release and letter dated April 9, 2024

Exhibit 99.1

April 2, 2024 POS AM

As filed with the Securities and Exchange Commission on April 2, 2024

As filed with the Securities and Exchange Commission on April 2, 2024 Registration No.

April 1, 2024 NT 10-K

UNITED STATES SECURITIES AND EXCHANGE Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☒ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: December 31, 2023 ☐ Transition Report on Form 10-K ☐

April 1, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: March 29, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

April 1, 2024 EX-99.1

Letter to stockholders dated March 29, 2024

Exhibit 99.1

March 14, 2024 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: March 12, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

March 14, 2024 EX-99.1

BLENDING LUXURY AND INVESTMENT: GAUCHO HOLDINGS INTRODUCES INNOVATIVE VINEYARD HOME RENTAL PROGRAM

Exhibit 99.1 PRESS RELEASE - FOR IMMEDIATE RELEASE BLENDING LUXURY AND INVESTMENT: GAUCHO HOLDINGS INTRODUCES INNOVATIVE VINEYARD HOME RENTAL PROGRAM Algodon Wine Estates Sets New Standards in Real Estate and Resort Living with Enhanced Website and Rental Offerings MIAMI, FL / MARCH 12, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce pla

March 7, 2024 EX-99.1

GAUCHO GROUP HOLDINGS, INC. (NASDAQ:VINO) UNVEILS ENHANCED WEBSITE FOR ALGODON WINE ESTATES, INTEGRATING LUXURY REAL ESTATE SALES AND RESORT BOOKINGS

Exhibit 99.1 FOR IMMEDIATE RELEASE GAUCHO GROUP HOLDINGS, INC. (NASDAQ:VINO) UNVEILS ENHANCED WEBSITE FOR ALGODON WINE ESTATES, INTEGRATING LUXURY REAL ESTATE SALES AND RESORT BOOKINGS Revamped Portal Offers Effortless Access to Exclusive Homesites and Unforgettable Resort Stays MIAMI, FL / MARCH 05, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of

March 7, 2024 8-K

Regulation FD Disclosure, Triggering Events That Accelerate or Increase a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement, Other Events, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: March 1, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41st

March 1, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 28, 2024 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 28, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

February 27, 2024 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Triggering Events That Accelerate or Increase a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement, Other Events, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 21, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

February 27, 2024 EX-99.1

Gaucho Responds to Notice of Default Gaucho Received Notice of Default from Convertible Promissory Noteholder

Exhibit 99.1 PRESS RELEASE – FOR IMMEDIATE RELEASE Gaucho Responds to Notice of Default Gaucho Received Notice of Default from Convertible Promissory Noteholder Miami, FL / February 27, 2024 / Gaucho Group Holdings, Inc. (NASDAQ: VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (the

February 20, 2024 EX-99.1

Complaint Filed with United States District Court for the District of Delaware on February 16, 2024

Exhibit 99.1

February 20, 2024 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 7, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

February 20, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 16, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

February 12, 2024 8-K

Unregistered Sales of Equity Securities, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 6, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

February 12, 2024 EX-99.1

GAUCHO HOLDINGS PROVIDES UPDATE ON MARKET ACTIVITY

Exhibit 99.1 PRESS RELEASE - FOR IMMEDIATE RELEASE GAUCHO HOLDINGS PROVIDES UPDATE ON MARKET ACTIVITY Asserting 2024 Goals, the Company Focuses on Asset Liquidation Expected to Yield USD 10-11 Million MIAMI, FL / February 12, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate,

February 12, 2024 SC 13G

US36809R4048 / GAUCHO GROUP HOL / 3i, LP - SC 13G Passive Investment

SC 13G 1 g08402313g.htm SC 13G SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Gaucho Group Holdings, Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 36809R404 (CUSIP Number) February 6, 2024 (Date of Event which Requires Filing of this Statement) Check the appropriate bo

February 7, 2024 8-K

Unregistered Sales of Equity Securities, Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 2, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

February 5, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 5, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

January 31, 2024 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: January 26, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

January 25, 2024 EX-99.1

GAUCHO GROUP HOLDINGS ANTICIPATES REVENUE SURGE AMID ARGENTINA’S MONETARY SHIFT

Exhibit 99.1 GAUCHO GROUP HOLDINGS ANTICIPATES REVENUE SURGE AMID ARGENTINA’S MONETARY SHIFT Milei’s Dollarization Strategy Can Mean Significant Revenue Increases For Company Assets MIAMI, FL / January 24, 2024 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods a

January 25, 2024 8-K

Unregistered Sales of Equity Securities, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: January 22, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

January 22, 2024 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☒ Defini

January 19, 2024 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 24, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 24, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

January 18, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: January 15, 2024 Gaucho Group Holdings, Inc. (Exact name of registr

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: January 15, 2024 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

January 18, 2024 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☒ Defini

January 18, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definitive Proxy Statement ☒ Definitive Additional Material ☐ Solicitation Mat

January 5, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 29, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 29, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

January 5, 2024 PRER14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Defini

December 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 20, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 20, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

December 20, 2023 EX-99.1

GAUCHO HOLDINGS ANNOUNCES FIRESIDE CHAT WITH CNBC AND FOX BUSINESS NETWORK MARKET ANALYST KENNY POLCARI

Exhibit 99.1 GAUCHO HOLDINGS ANNOUNCES FIRESIDE CHAT WITH CNBC AND FOX BUSINESS NETWORK MARKET ANALYST KENNY POLCARI A Strategic Discussion on Argentina’s Investment Landscape Post-political Shift, Featuring Insights From CEO Scott Mathis MIAMI, FL / December 20, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentrat

December 19, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definitive Proxy Statement ☒ Definitive Additional Material ☐ Solicitation Mat

December 19, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 19, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 19, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

December 19, 2023 EX-99.1

Gaucho Group Holdings, INc. Announces the Postponement of its Special Stockholder MEeting

Exhibit 99.1 Gaucho Group Holdings, INc. Announces the Postponement of its Special Stockholder MEeting MIAMI, FL / December 19, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO) has announced that its Special Meeting of Stockholders, scheduled to be held at 12:00 p.m. Eastern Time on Thursday, December 28, 2023 (the “Stockholder Meeting”) has been postponed and will now take place on Thursday, Febr

December 14, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 8, 2023 Gaucho Group Holdings, Inc. (Exact name of registr

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 8, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

December 14, 2023 EX-99.1

Press release, dated December 13, 2023

Exhibit 99.1

December 13, 2023 8-K

Unregistered Sales of Equity Securities, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 7, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

December 13, 2023 8-K/A

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 30, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE

December 13, 2023 EX-99.1

GAUCHO HOLDINGS HIRES the basile law firm P.C. to recommend courses of action that may bring value to the company and its Stockholders

Exhibit 99.1 GAUCHO HOLDINGS HIRES the basile law firm P.C. to recommend courses of action that may bring value to the company and its Stockholders MIAMI, FL / December 13, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (the “Company” or

December 6, 2023 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 30, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

December 4, 2023 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 4, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

December 4, 2023 EX-99.1

GAUCHO HOLDINGS WELCOMES REAL ESTATE VISIONARY MICHAEL KOH TO ADVISORY BOARD

Exhibit 99.1 GAUCHO HOLDINGS WELCOMES REAL ESTATE VISIONARY MICHAEL KOH TO ADVISORY BOARD Strategic Move Strengthens Gaucho Holdings’ Position in the Evolving Luxury Market of Post-Election Argentina MIAMI, FL / DECEMBER 4, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, a

December 1, 2023 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 20, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

November 30, 2023 EX-99.1

GAUCHO HOLDINGS SEIZES NEW OPPORTUNITIES WITH NASDAQ EXTENSION AND ARGENTINE ECONOMIC REVIVAL

Exhibit 99.1 GAUCHO HOLDINGS SEIZES NEW OPPORTUNITIES WITH NASDAQ EXTENSION AND ARGENTINE ECONOMIC REVIVAL A Decade of Argentine Investment Poised to Deliver in Evolving Market MIAMI, FL / November 30, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and a

November 30, 2023 EX-99.2

GAUCHO HOLDINGS WELCOMES DOUG CASEY AS LEAD BUSINESS ADVISOR, BOLSTERING ARGENTINA INVESTMENT STRATEGY

Exhibit 99.2 GAUCHO HOLDINGS WELCOMES DOUG CASEY AS LEAD BUSINESS ADVISOR, BOLSTERING ARGENTINA INVESTMENT STRATEGY Renowned Author and Speculator to Guide Company’s Growth in the Wake of Argentina’s Opportunistic Economic Shift MIAMI, FL / NOVEMBER 30, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fin

November 30, 2023 8-K

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 29, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 4

November 28, 2023 EX-99.1

From the Desk of Scott Mathis

Exhibit 99.1 From the Desk of Scott Mathis Direct: 212.739.7650 Fax: 212.655.0140 [email protected] November 28, 2023 Via email: [email protected] Nasdaq Stock Market Listing Qualifications Department Attn: W. Wayne Bush, CFA, Director Re: Gaucho Group Holdings, Inc. (the “Company”) Nasdaq Security: Common Stock Nasdaq Symbol: VINO Dear Mr. Bush: On June 1, 2023, Gaucho Group Holdings

November 28, 2023 8-K

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 28, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

November 27, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 27, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 27, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 4

November 24, 2023 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☒ Defini

November 21, 2023 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 21, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

November 21, 2023 EX-99.1

Press release dated November 20, 2023

Exhibit 99.1

November 20, 2023 EX-99.1

“A HISTORIC LEAP FOR ARGENTINA’S ECONOMY”: GAUCHO GROUP HOLDINGS HAILS PRESIDENTIAL ELECTION AS CATALYST FOR UNPRECEDENTED GROWTH

Exhibit 99.1 “A HISTORIC LEAP FOR ARGENTINA’S ECONOMY”: GAUCHO GROUP HOLDINGS HAILS PRESIDENTIAL ELECTION AS CATALYST FOR UNPRECEDENTED GROWTH Chairman Scott Mathis Shares Insight on Argentina’s Potentially Transformative Era for Argentine Real Estate and Economic Growth MIAMI, FL / November 20, 2023 / Gaucho Group Holdings, Inc. (Gaucho Holdings) (Gauchoholdings.com) (NASDAQ: VINO), an organizati

November 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 20, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 20, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

November 20, 2023 EX-99.2

Stockholder update dated November 20, 2023

Exhibit 99.2

November 17, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 ☐ TRANSITION REPORT UNDER S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to . Commission file number: 001-40075 Gaucho Group Holdin

November 14, 2023 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: September 30, 2023 ☐ Transition Report on Form 10-K

November 13, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☒ Definit

November 13, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definitive Proxy Statement ☒ Definitive Additional Material ☐ Solicitation Mat

November 6, 2023 PRER14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Defini

November 3, 2023 PRER14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Defini

October 27, 2023 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definit

October 20, 2023 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 16, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

October 17, 2023 EX-99.1

Stockholder update dated October 16, 2023

Exhibit 99.1

October 17, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 16, 2023 Gaucho Group Holdings, Inc. (Exact name of registr

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 16, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41

October 10, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 9, 2023 Gaucho Group Holdings, Inc. (Exact name of registra

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 9, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41s

October 10, 2023 8-K

Other Events, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 4, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41s

October 10, 2023 EX-10.1

Second Amendment to Senior Secured Convertible Note, dated as of October 9, 2023, by and among Gaucho Group Holdings, Inc. and the holder listed therein

Exhibit 10.1 SECOND AMENDMENT TO SENIOR SECURED CONVERTIBLE NOTE This Second Amendment to Senior Secured Convertible Note (this “Amendment”) dated as of October 9, 2023 (the “Effective Date”) is entered into by and between Gaucho Group Holdings Inc., a Delaware corporation (the “Company”), and , (the “Purchaser”). RECITALS A. The Purchaser and the Company entered into that certain Securities Purch

October 10, 2023 EX-99.2

Gaucho Group Holdings, Inc.: The Case for Investing in Argentina

Exhibit 99.2 Gaucho Group Holdings, Inc.: The Case for Investing in Argentina A Glimpse into Argentina’s Economic Potential Despite often finding itself amidst negative headlines, Argentina’s stock market stands tall, representing one of the globe’s best performers. This not only defies the general skepticism surrounding the country but also underscores the immense confidence international investo

October 10, 2023 EX-99.1

SUSTAINABILITY MEETS LUXURY: GAUCHO HOLDINGS BEGINS PROCESS TO CONVERT SELECT VINEYARDS IN ITS PORTFOLIO TO ORGANIC CULTIVATION

Exhibit 99.1 SUSTAINABILITY MEETS LUXURY: GAUCHO HOLDINGS BEGINS PROCESS TO CONVERT SELECT VINEYARDS IN ITS PORTFOLIO TO ORGANIC CULTIVATION Gaucho’s Algodon Wine Estates Embarks on Organic Journey, Amplifying Wine Excellence and Stockholder Value MIAMI, FL / October 10, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a co

October 5, 2023 EX-10.1

First Amendment to Senior Secured Convertible Note, dated as of October 5, 2023, by and among Gaucho Group Holdings, Inc. and the holder listed therein

Exhibit 10.1 FIRST AMENDMENT TO SENIOR SECURED CONVERTIBLE NOTE This First Amendment to Senior Secured Convertible Note (this “Amendment”) dated as of October 5, 2023 (the “Effective Date”) is entered into by and between Gaucho Group Holdings Inc., a Delaware corporation (the “Company”), and , (the “Purchaser”). RECITALS A. The Purchaser and the Company entered into that certain Securities Purchas

October 5, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 5, 2023 Gaucho Group Holdings, Inc. (Exact name of registra

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 5, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41s

October 4, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 4, 2023 Gaucho Group Holdings, Inc. (Exact name of registra

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: October 4, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 41s

October 4, 2023 EX-99.1

GAUCHO GROUP HOLDINGS, INC. ANNOUNCES NEW INITIATIVES TO INCREASE STOCKHOLDER VALUE

Exhibit 99.1 GAUCHO GROUP HOLDINGS, INC. ANNOUNCES NEW INITIATIVES TO INCREASE STOCKHOLDER VALUE Sale of Non-Core Assets Enables Company to Sharpen Focus on Key Business Ventures MIAMI, FL / October 4, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and a

October 2, 2023 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 26, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE

September 29, 2023 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 27, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE

September 29, 2023 EX-10.1

Letter Agreement regarding LVH Holdings LLC, dated September 27, 2023

Exhibit 10.1 SLVH LLC 23 Corporate Plaza, Suite 150 Newport Beach, California 92660 September 27, 2023 Gaucho Ventures I – Las Vegas, LLC c/o Gaucho Group Holdings, Inc. 112 NE 41st Street, Suite 106 Miami, Florida 33137 Attn: Scott Mathis Re: LVH Holdings LLC – Suspension of Business Mr. Mathis: SLVH LLC, a Delaware limited liability company (“SLVH Member” or “Manager”) and Gaucho Ventures I – La

September 25, 2023 EX-99.1

Company Update as of September 25, 2023

Exhibit 99.1

September 25, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 25, 2023 Gaucho Group Holdings, Inc. (Exact name of regis

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 25, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE

September 22, 2023 EX-3.1

Amended and Restated Certificate of Incorporation filed with the Delaware Secretary of State effective September 25, 2023 (29)

Exhibit 3.1 AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF GAUCHO GROUP HOLDINGS, INC. Gaucho Group Holdings, Inc., a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (the “Corporation”), does hereby certify that: 1. The original name of the Corporation was Investprivate.com, Inc. The Corporation’s original Certificate of Incorpor

September 22, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 22, 2023 Gaucho Group Holdings, Inc. (Exact name of regis

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 22, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE

September 22, 2023 EX-99.1

GAUCHO GROUP HOLDINGS, INC. ANNOUNCES REVERSE STOCK SPLIT

Exhibit 99.1 GAUCHO GROUP HOLDINGS, INC. ANNOUNCES REVERSE STOCK SPLIT VINO common stock expected to begin trading on a split-adjusted basis on September 25, 2023 MIAMI, FL / SEPTEMBER 22, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and leather goods and accessories (t

September 18, 2023 8-K

Unregistered Sales of Equity Securities

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: September 15, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE

September 5, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 30, 2023 Gaucho Group Holdings, Inc. (Exact name of registra

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 30, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41s

August 28, 2023 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 24, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 24, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Incorporation Commission File Number IRS Employer Identification No. 112 NE 4

August 25, 2023 8-K

Submission of Matters to a Vote of Security Holders, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 24, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41s

August 14, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 ☐ TRANSITION REPORT UNDER SECTIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 OR ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to . Commission file number: 001-40075 Gaucho Group Holdings, I

August 11, 2023 8-K

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: August 11, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41s

August 11, 2023 EX-10.1

Letter Agreement, dated as of August 11, 2023, by and among Gaucho Group Holdings, Inc. and the subscriber listed therein

Exhibit 10.1 From the Desk of Scott Mathis Direct: 212.739.7650 Fax: 212.655.0140 [email protected] August 11, 2023 3i, LP 2 Wooster Street, Floor 2 New York, NY 10013 Re: Modification to Purchase Agreement Dear Sirs: Reference is made to (a) that certain Securities Purchase Agreement dated as of February 21, 2023 (the “Purchase Agreement”) between the Company and the purchaser identified

July 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 14, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: July 14, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st

July 11, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definitive Proxy Statement ☒ Definitive Additional Material ☐ Solicitation Mat

July 10, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☒ Definitive Proxy Statement ☐ Definitive Additional Material ☐ Solicitation Material under §240.

July 7, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 27, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 27, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st

July 5, 2023 EX-10.1

Fourth Amendment to Amended and Restated Limited Liability Agreement dated June 30, 2023 (27)

Exhibit 10.1 FOURTH AMENDMENT TO AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT This FOURTH AMENDMENT TO AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT (this “Fourth Amendment”) is entered into as of June 30, 2023 (the “Fourth Amendment Date”), by and between SLVH LLC, a Delaware limited liability company (the “SLVH Member”), and Gaucho Ventures I - Las Vegas LLC, a Delaware li

July 5, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 30, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 30, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st

June 29, 2023 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definitive Proxy Statement ☐ Definitive Additional Material ☐ Solicitation Material under §240.

June 12, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 12, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 12, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st

June 6, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 1, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 1, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st S

May 31, 2023 424B3

Gaucho Group Holdings, Inc. 2,000,000 Shares

Filed Pursuant to Rule 424(b)(3) Registration No. 333-271761 PROSPECTUS Gaucho Group Holdings, Inc. 2,000,000 Shares This prospectus relates to the resale from time to time of up to 2,000,000 shares of our common stock, par value $0.01 per share by the selling stockholders set forth under the caption “Selling Stockholders” beginning on page 12 of this prospectus (each individually as a “selling st

May 24, 2023 CORRESP

Via Edgar

Via Edgar May 24, 2023 Division of Corporate Finance United States Securities and Exchange Commission Office of Real Estate and Construction 100 F Street, NE Washington, DC 20549 Re: Gaucho Group Holdings, Inc.

May 22, 2023 S-1/A

As filed with the Securities and Exchange Commission on May 22, 2023

As filed with the Securities and Exchange Commission on May 22, 2023 Registration No.

May 22, 2023 EX-FILING FEES

EX-Filing Fees*

Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Gaucho Group Holdings, Inc.

May 19, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 ☐ TRANSITION REPORT UNDER SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to . Commission file number: 001-40075 Gaucho Group Holdings,

May 15, 2023 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: March 31, 2023 ☐ Transition Report on Form 10-K ☐ Tr

May 10, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 8, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant a

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 8, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st St

May 10, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 2, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant a

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 2, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st St

May 9, 2023 EX-FILING FEES

EX-Filing Fees*

Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Gaucho Group Holdings, Inc.

May 9, 2023 S-1

As filed with the Securities and Exchange Commission on May 9, 2023

As filed with the Securities and Exchange Commission on May 9, 2023 Registration No.

May 8, 2023 EX-99.1

Letter to stockholders dated May 8, 2023

Exhibit 99.1

May 8, 2023 EX-99.2

GAUCHO GROUP HOLDINGS PROJECTS OVER $6 MILLION IN SALES IN 2023 DRIVEN BY STRONG DEMAND FOR LUXURY REAL ESTATE PROPERTIES

Exhibit 99.2 GAUCHO GROUP HOLDINGS PROJECTS OVER $6 MILLION IN SALES IN 2023 DRIVEN BY STRONG DEMAND FOR LUXURY REAL ESTATE PROPERTIES Vineyard Real Estate Project Drives Growth, While Offering a Diversified Investment With Exceptional Lifestyle Offerings Miami, FL / May 8, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a

May 8, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 8, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant a

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: May 8, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st St

April 24, 2023 424B3

Gaucho Group Holdings, Inc. 1,519,454 Shares

Filed Pursuant to Rule 424(b)(3) Registration No. 333-271305 PROSPECTUS Gaucho Group Holdings, Inc. 1,519,454 Shares This prospectus relates to the resale from time to time of up to 1,519,454 shares of our common stock, par value $0.01 per share by the selling stockholders set forth under the caption “Selling Stockholders” beginning on page 12 of this prospectus (each individually as a “selling st

April 20, 2023 CORRESP

Via Edgar

Via Edgar April 20, 2023 Division of Corporate Finance United States Securities and Exchange Commission Office of Real Estate and Construction 100 F Street, NE Washington, DC 20549 Re: Gaucho Group Holdings, Inc.

April 20, 2023 CORRESP

Via Edgar

Via Edgar April 20, 2023 Division of Corporate Finance United States Securities and Exchange Commission Office of Real Estate and Construction 100 F Street, NE Washington, DC 20549 Re: Gaucho Group Holdings, Inc.

April 19, 2023 CORRESP

Via Edgar

Via Edgar April 19, 2023 Division of Corporate Finance United States Securities and Exchange Commission Office of Real Estate and Commodities 100 F Street, NE Washington, DC 20549 Re: Gaucho Group Holdings, Inc.

April 18, 2023 S-1

As filed with the Securities and Exchange Commission on April 17, 2023

As filed with the Securities and Exchange Commission on April 17, 2023 Registration No.

April 18, 2023 EX-FILING FEES

EX-Filing Fees*

Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Gaucho Group Holdings, Inc.

April 17, 2023 10-K

Form 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K (Mark one) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Fiscal Year Ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40075 Gaucho Group Hold

April 17, 2023 EX-99.1

Algodon Wine Estates Property Map(37)

Exhibit 99.1

April 17, 2023 EX-4.19

Description of Capital Stock of the Company*

Exhibit 4.19 DESCRIPTION OF OUR SECURITIES The following description summarizes important terms of our capital stock and our other securities. For a complete description, you should refer to our Certificate of Incorporation and bylaws, forms of which are incorporated by reference to this annual report, as well as the relevant portions of the Delaware General Corporation Law (“DGCL”). Capital Stock

April 4, 2023 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 18, 2022 Gaucho Group Holdings, Inc. (Exact name of regi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 18, 2022 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE

April 4, 2023 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 7, 2022 Gaucho Group Holdings, Inc. (Exact name of registran

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: June 7, 2022 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41st

March 31, 2023 NT 10-K

UNITED STATES SECURITIES AND EXCHANGE Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 OMB APPROVAL OMB Number: 3235- 0058 Estimated average burden hours per response .... 2.50 NOTIFICATION OF LATE FILING SEC FILE NUMBER CUSIP NUMBER (Check one): ☒ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: December 31, 2022 ☐ Transition Report on Form 10-K ☐

March 23, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definit

March 23, 2023 DEF 14A

Schedule 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☒ Definit

March 13, 2023 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party Other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for use of the Commission only as permitted by Rule 14a-6(e)(2) ☐ Definit

February 21, 2023 EX-10.4

Form of Security and Pledge Agreement

Exhibit 10.4 Execution Version SECURITY AND PLEDGE AGREEMENT SECURITY AND PLEDGE AGREEMENT, dated as of February 21, 2023 (this “Agreement”), made by Gaucho Group Holdings, Inc., a Delaware corporation with offices located at 112 NE 41st Street, Suite 106, Miami, Florida 33137 (the “Company”), and each of the undersigned grantors, if any (each a “Grantor” and together with the Company, collectivel

February 21, 2023 EX-99.1

GAUCHO GROUP HOLDINGS, INC ANNOUNCES SECUREMENT OF $5.6 MILLION CONVERTIBLE NOTE

Exhibit 99.1 GAUCHO GROUP HOLDINGS, INC ANNOUNCES SECUREMENT OF $5.6 MILLION CONVERTIBLE NOTE Company Continues to Lay Foundation to Pursue Objectives in Growth and Scale of its Diverse Assets MIAMI, FL / February 21, 2023 / Gaucho Group Holdings, Inc. (NASDAQ:VINO), a company that includes a growing collection of e-commerce platforms with a concentration on fine wines, luxury real estate, and lea

February 21, 2023 EX-4.1

Form Warrant (36)

Exhibit 4.1 [FORM OF WARRANT] NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE EXERCISABLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATI

February 21, 2023 EX-10.1

Exchange Agreement, dated as of February 20, 2023, by and among Gaucho Group Holdings, Inc. and the subscribers listed therein. (35)

Exhibit 10.1 EXECUTION VERSION AMENDMENT AND EXCHANGE AGREEMENT This Amendment and Exchange Agreement (the “Agreement”) is entered into as of the 20th day of February, 2023, by and among Gaucho Group Holdings, Inc., a Delaware corporation (the “Company”) and the investor signatory hereto (the “Holder”), with reference to the following facts: A. Prior to the date hereof, pursuant to that Securities

February 21, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 21, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 21, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 4

February 21, 2023 EX-10.6

Form of Registration Rights Agreement

Exhibit 10.6 REGISTRATION RIGHTS AGREEMENT This REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of February 21, 2023, is by and among Gaucho Group Holdings Inc., a Delaware corporation with offices located at 112 NE 41st Street, Suite 106, Miami, Florida 33137 (the “Company”), and the undersigned buyers (each, a “Buyer,” and collectively, the “Buyers”). RECITALS A. In connection with th

February 21, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 20, 2023 Gaucho Group Holdings, Inc. (Exact name of regist

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 20, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 4

February 21, 2023 EX-10.3

Form Warrant (35)

Exhibit 10.3 Execution Version NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE EXERCISABLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRAT

February 21, 2023 EX-10.1

Securities Purchase Agreement dated February 21, 2023

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the “Agreement”), dated as of February 21, 2023, is by and among Gaucho Group Holdings Inc., a Delaware corporation with offices located at 112 NE 41st Street, Suite 106, Miami, Florida 33137 (the “Company”), and each of the investors listed on the Schedule of Buyers attached hereto (individually, a “Buyer” and collecti

February 21, 2023 EX-10.2

Form of Senior Secured Convertible Note Issued by the Company(36)

Exhibit 10.2 Execution Version SENIOR SECURED CONVERTIBLE NOTE NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSEN

February 21, 2023 EX-10.5

Form of Stockholder Pledge Agreement

Exhibit 10.5 Execution STOCKHOLDER PLEDGE AGREEMENT This STOCKHOLDER PLEDGE AGREEMENT (this “Agreement”), dated as of February 21, 2023, is made by , a , with a principal address at (the “Pledgor”), Gaucho Group Holdings Inc., a Delaware corporation with offices located at 112 NE 41st Street, Suite 106, Miami, Florida 33137 (the “Company”), and the Secured Party listed on the signature page hereof

February 15, 2023 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 10, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 4

February 15, 2023 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 30, 2022 Gaucho Group Holdings, Inc. (Exact name of regi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: November 30, 2022 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE

February 15, 2023 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 19, 2022 Gaucho Group Holdings, Inc. (Exact name of regi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: December 19, 2022 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE

February 8, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 8, 2023 Gaucho Group Holdings, Inc. (Exact name of registr

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 8, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41

February 8, 2023 EX-10.1

Letter Agreement, dated as of February 8, 2023, by and among Gaucho Group Holdings, Inc. and the Holders listed therein. (34)

Exhibit 10.1 From the Desk of Scott Mathis Direct: 212.739.7650 Fax: 212.655.0140 [email protected] February 8, 2023 3i, LP 140 Broadway Floor 38 New York, NY 10005 Nomis Bay, Ltd. Wessex House 3rd Floor 45 Reid Street Hamilton, HM 12 Bermuda BPY Limited Wessex House 3rd Floor 45 Reid Street Hamilton, HM 12 Bermuda Re: Modification to Purchase Agreement Dear Sirs: Reference is made to (a)

February 3, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 2, 2023 Gaucho Group Holdings, Inc. (Exact name of registr

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report: February 2, 2023 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-40075 52-2158952 State of Commission IRS Employer Incorporation File Number Identification No. 112 NE 41

February 3, 2023 EX-10.1

Letter Agreement, dated as of February 2, 2023, by and among Gaucho Group Holdings, Inc. and the Holders listed therein. (33)

Exhibit 10.1 From the Desk of Scott Mathis Direct: 212.739.7650 Fax: 212.655.0140 [email protected] February 2, 2023 3i, LP 140 Broadway Floor 38 New York, NY 10005 Nomis Bay, Ltd. Wessex House 3rd Floor 45 Reid Street Hamilton, HM 12 Bermuda BPY Limited Wessex House 3rd Floor 45 Reid Street Hamilton, HM 12 Bermuda Re: Conversion Price Voluntary Adjustment Notice Dear Sirs: Reference is m

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