OSBC / Old Second Bancorp, Inc. - SEC फाइलिंग, वार्षिक रिपोर्ट, प्रॉक्सी स्टेटमेंट

ओल्ड सेकेंड बैनकॉर्प, इंक.
US ˙ NasdaqGS ˙ US6802771005

मूलभूत आँकड़े
LEI 549300XVJC1MPUT81C04
CIK 357173
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 Old Second Bancorp, 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 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

July 23, 2025 EX-99.1

Old Second Bancorp, Inc. Reports Second Quarter 2025 Net Income of $21.8 Million, or $0.48 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer July 23, 2025 (630) 906-5484 Old Second Bancorp, Inc. Reports Second Quarter 2025 Net Income of $21.8 Million, or $0.48 per Diluted Share AURORA, IL, July 23, 2025 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second National

July 23, 2025 EX-99.2

2 Portfolio Segment Outstanding Classified Allowance Commercial (incl. Leases) $1,243 $25 0.76% Commercial Real Estate Investor $1,119 $15 1.51% Commercial Real Estate Owner Occ. $652 $51 1.19% Construction $252 $2 1.14% Residential Real Estate $272

1 Loan Portfolio Disclosures AS OF JUNE 30, 2025 Exhibit 99.2 2 Portfolio Segment Outstanding Classified Allowance Commercial (incl. Leases) $1,243 $25 0.76% Commercial Real Estate Investor $1,119 $15 1.51% Commercial Real Estate Owner Occ. $652 $51 1.19% Construction $252 $2 1.14% Residential Real Estate $272 $3 0.92% Multifamily $334 $1 0.51% HELOC $111 $1 1.59% Other $16 - 0.33% Total $3,999 $9

July 23, 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 (Date of earliest event reported): July 23, 2025 (Exact name of regi

I 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 (Date of earliest event reported): July 23, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

July 15, 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 (Date of earliest event reported): July 15, 2025 (Exact name of regi

I 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 (Date of earliest event reported): July 15, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

July 2, 2025 8-K

Current Report

I 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 (Date of earliest event reported): July 2, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

July 1, 2025 EX-99.1

Old Second Completes Merger with Bancorp Financial

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, July 1, 2025 Chief Operating Officer and Chief Financial Officer (630) 906-5484 Old Second Completes Merger with Bancorp Financial AURORA, Illinois July 1, 2025 (PRNewswire) — Old Second Bancorp, Inc. (Nasdaq: OSBC) (“Old Second”) announced today that it has completed its previously announced merge

July 1, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets, Other Events

I 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 (Date of earliest event reported): July 1, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

July 1, 2025 EX-10.2

Compensation and Benefits Assurance Agreement, dated July 1, 2025, between Old Second Bancorp, Inc. and Darin Campbell. +

Exhibit 10.2 COMPENSATION AND BENEFITS ASSURANCE AGREEMENT Darin Campbell EXECUTIVE C-1 COMPENSATION AND BENEFITS ASSURANCE AGREEMENT This COMPENSATION AND BENEFITS ASSURANCE AGREEMENT (this “Agreement”) is made, entered into, and is effective as of July 1, 2025 (the “Effective Date”) by and between OLD SECOND BANCORP, INC. (hereinafter referred to as the “Company”) and DARIN CAMPBELL (hereinafter

July 1, 2025 EX-10.1

Executive Employment Agreement, dated February 24, 2025, between Old Second Bancorp, Inc. and Darin Campbell.

Exhibit 10.1 EXECUTIVE EMPLOYMENT AGREEMENT This EMPLOYMENT AGREEMENT (the “Agreement”) is entered into effective as of February 24, 2025 (“Effective Date”), by and between OLD SECOND BANCORP, INC. (the “Company”) and DARIN CAMPBELL (the “Executive”). RECITALS WHEREAS, the Company and its wholly-owned subsidiary, Old Second National Bank (the “Bank”) are presently engaged in the general business o

June 30, 2025 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 11-K ANNUAL REPORT Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the

11-K 1 tmb-20241231x11k.htm 11-K I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 11-K ANNUAL REPORT Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR oTRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT

June 18, 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 (Date of earliest event reported): June 18, 2025 (Exact name of regi

I 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 (Date of earliest event reported): June 18, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

June 3, 2025 8-K/A

United States Securities And Exchange Commission Washington, D.C. 20549 FORM 8-K/A (AMENDMENT NO. 1) Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 20, 2025

I United States Securities And Exchange Commission Washington, D.C. 20549 FORM 8-K/A (AMENDMENT NO. 1) Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 20, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File

June 2, 2025 S-8

As filed with the Securities and Exchange Commission on June 2, 2025

As filed with the Securities and Exchange Commission on June 2, 2025 Registration No.

June 2, 2025 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) Old Second Bancorp, Inc.

May 28, 2025 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

I 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 (Date of earliest event reported): May 23, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 28, 2025 EX-3.1

Amendment to Old Second Bancorp, Inc.’s Restated Certificate of Incorporation.

Exhibit 3.1 CERTIFICATE OF AMENDMENT TO THE RESTATED CERTIFICATE OF INCORPORATION OF OLD SECOND BANCORP, INC. (Pursuant to 8 Del. C. Section 242) Old Second Bancorp, Inc. (the “Corporation”), a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware, does hereby certify: FIRST: That at a meeting of the Board of Directors of the Corporation, re

May 22, 2025 EX-99.1

Old Second Bancorp, Inc. Announces Receipt of Regulatory Approvals to Complete its Merger Transaction with Bancorp Financial, Inc.

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, May 22, 2025 Chief Operating Officer and Chief Financial Officer (630) 906-5484 Old Second Bancorp, Inc. Announces Receipt of Regulatory Approvals to Complete its Merger Transaction with Bancorp Financial, Inc. Aurora, Illinois May 22, 2025 - Old Second Bancorp, Inc. (Nasdaq: OSBC) (“Old Second”) a

May 22, 2025 8-K

Financial Statements and Exhibits, Other Events

I 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 (Date of earliest event reported): May 22, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 20, 2025 EX-99.1

Old Second Bancorp, Inc. Annual Stockholders Meeting

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, May 20, 2025 Chief Operating Officer and Chief Financial Officer (630) 906-5484 Old Second Bancorp, Inc. Annual Stockholders Meeting AURORA, IL, – Old Second Bancorp, Inc. (“Old Second”) (NASDAQ: OSBC), announced the Annual Stockholders Meeting will be held on May 20, 2025 at 9:00 am CDT. Sharehold

May 20, 2025 8-K

Submission of Matters to a Vote of Security Holders

I 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 (Date of earliest event reported): May 20, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 20, 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 (Date of earliest event reported): May 20, 2025 (Exact name of regis

I 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 (Date of earliest event reported): May 20, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 15, 2025 424B3

Supplement to the Proxy Statement/Prospectus Dated May 8, 2025

Proxy Statement/Prospectus Supplement to Proxy Statement/Prospectus dated May 8, 2025 Filed Pursuant to Rule 424(b)(3) Registration Statement No.

May 9, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

May 9, 2025 EX-10.1

Form of Performance-Based Restricted Stock Unit Agreement

Exhibit 10.1 OLD SECOND BANCORP, INC. 2019 EQUITY INCENTIVE PLAN, AS AMENDED AND RESTATED PERFORMANCE-BASED RESTRICTED STOCK UNIT AGREEMENT The Participant specified below has been granted a restricted stock unit award (the “Award”) by Old Second Bancorp, Inc., a Delaware corporation (the “Company”), under the Old Second Bancorp, Inc. 2019 Equity Incentive Plan, As Amended and Restated (the “Plan”

May 8, 2025 424B3

MERGER PROPOSED — YOUR VOTE IS VERY IMPORTANT

TABLE OF CONTENTS  Filed pursuant to Rule 424(b)(3)  Registration No. 333-286687 MERGER PROPOSED — YOUR VOTE IS VERY IMPORTANT To the Stockholders of Bancorp Financial, Inc.: On February 24, 2025, Old Second Bancorp, Inc., which we refer to as “Old Second,” and Bancorp Financial, Inc., which we refer to as “Bancorp Financial,” entered into an Agreement and Plan of Merger, which we refer to as the

May 6, 2025 EX-99.3

Form of Proxy Card to be used by Bancorp Financial.**

Exhibit 99.3 Signature of Stockholder Date: Signature of Stockholder Date: Note: Please sign exactly as your name or names appear on this Proxy. When shares are held jointly, each holder should sign. When signing as executor, administrator, attorney, trustee or guardian, please give full title as such. If the signer is a corporation, please sign full corporate name by duly authorized officer, givi

May 6, 2025 CORRESP

May 6, 2025

May 6, 2025 Via Edgar U.S. Securities and Exchange Commission Division of Corporation Finance Office of Finance Washington, D.C. 20549 Attention: Aisha Adegbuyi Re: Request for Acceleration Old Second Bancorp, Inc. (the “Registrant”) Registration Statement on Form S-4 (File No. 333-286687) Dear Sir or Madam: Pursuant to Rule 461 under the Securities Act of 1933, as amended (the “Securities Act”),

May 6, 2025 S-4/A

As filed with the U.S. Securities and Exchange Commission on May 6, 2025

TABLE OF CONTENTS As filed with the U.S. Securities and Exchange Commission on May 6, 2025 File No. 333-286687 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to FORM S-4 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 OLD SECOND BANCORP, INC. (Exact Name of Registrant as Specified in its Charter) Delaware (State or Other Jurisdiction of Incorporatio

April 23, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

I 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 (Date of earliest event reported): April 23, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. E

April 23, 2025 EX-99.1

Consent of Keefe, Bruyette & Woods, Inc.*

Exhibit 99.1 CONSENT OF KEEFE, BRUYETTE & WOODS, INC. We hereby consent to the inclusion of our opinion letter to the Board of Directors of Bancorp Financial, Inc. (“Bancorp Financial”), as Annex B to the proxy statement/prospectus which forms a part of the Registration Statement on Form S-4 filed on the date hereof (the “Registration Statement”) relating to the proposed merger of Bancorp Financia

April 23, 2025 EX-FILING FEES

Filing Fee Table.*

Exhibit 107 Calculation of Filing Fee Tables Form S-4 (Form Type) Old Second Bancorp, Inc.

April 23, 2025 EX-99.2

Consent of Darin Campbell to be named as director.*

Exhibit 99.2 CONSENT OF DIRECTOR-NOMINEE This Consent of Director-Nominee is delivered in connection with the registration statement on Form S-4 of Old Second Bancorp, Inc. to be filed with the U.S. Securities Exchange Commission (as it may be amended from time to time, the “Registration Statement”) for the registration under the Securities Act of 1933, as amended, of the shares of Old Second Banc

April 23, 2025 S-4

As filed with the U.S. Securities and Exchange Commission on April 23, 2025

TABLE OF CONTENTS As filed with the U.S. Securities and Exchange Commission on April 23, 2025 File No. 333-       UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-4 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 OLD SECOND BANCORP, INC. (Exact Name of Registrant as Specified in its Charter) Delaware (State or Other Jurisdiction of Incorporation or Organizatio

April 23, 2025 EX-99.2

2 Portfolio Segment Outstanding Classified Allowance Commercial (incl. Leases) $1,238 $22 0.81% Commercial Real Estate Investor $1,105 $14 1.41% Commercial Real Estate Owner Occ. $670 $27 1.08% Construction $205 $18 1.30% Residential Real Estate $260

1 Loan Portfolio Disclosures AS OF MARCH 31, 2025 Exhibit 99.2 2 Portfolio Segment Outstanding Classified Allowance Commercial (incl. Leases) $1,238 $22 0.81% Commercial Real Estate Investor $1,105 $14 1.41% Commercial Real Estate Owner Occ. $670 $27 1.08% Construction $205 $18 1.30% Residential Real Estate $260 $3 0.92% Multifamily $341 - 0.54% HELOC $105 $1 1.60% Other $16 - 0.06% Total $3,940 $

April 23, 2025 EX-99.1

Old Second Bancorp, Inc. Reports First Quarter 2025 Net Income of $19.8 Million, or $0.43 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer April 23, 2025 (630) 906-5484 Old Second Bancorp, Inc. Reports First Quarter 2025 Net Income of $19.8 Million, or $0.43 per Diluted Share AURORA, IL, April 23, 2025 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second Nationa

April 18, 2025 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)) ⌧ Defin

April 15, 2025 8-K

Current Report

I 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 (Date of earliest event reported): April 15, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. E

April 1, 2025 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)) ◻ Defin

April 1, 2025 8-K

Current Report

I 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 (Date of earliest event reported): April 1, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

March 6, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ⌧ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ◻ 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 000-10537 (Exact n

March 6, 2025 EX-19.1

Insider Trading Policy

Exhibit 19.1 OLD SECOND BANCORP, INC. POLICY REGARDING TRADING IN COMPANY SECURITIES AND CONFIDENTIALITY OF INFORMATION Introduction As a publicly traded company, Old Second Bancorp, Inc. (the “Company”) has certain legal and ethical responsibilities with respect to the market for its securities and the confidentiality of information about the Company and the Company’s clients and other business a

March 6, 2025 EX-21.1

A list of all subsidiaries of the Company.

Exhibit 21.1 LIST OF SUBSIDIARIES Subsidiaries of the Company Incorporated Under Laws of Percent Owned by the Company Old Second National Bank United States 100% of the common stock Old Second Capital Trust II State of Delaware 100% of the common stock Old Second Affordable Housing Fund, L.L.C. State of Illinois Owned by Old Second National Bank Station I, LLC State of Illinois Owned by Old Second

March 6, 2025 EX-97

Old Second Bancorp, Inc. Clawback Policy dated August 15, 2023.

Exhibit 97 OLD SECOND BANCORP, INC. Incentive Compensation Recovery Policy (the “Policy”) A. Mandatory Clawback for Section 16 Officers. 1.Recovery of Excess Incentive Compensation. If Old Second Bancorp, Inc. (the “Company”) is required to prepare a Restatement, the Company’s board of directors (the “Board”) shall, unless the Board’s Compensation Committee (the “Compensation Committee”) determine

March 6, 2025 EX-4.5

Description of Capital Stock.

Exhibit 4.5 DESCRIPTION OF OLD SECOND BANCORP, INC. CAPITAL STOCK References to “we,” “us” or “our” and the “Company” herein refer to Old Second Bancorp, Inc., a Delaware corporation. This summary does not purport to be complete and is subject to and is qualified in its entirety by reference to our the applicable provisions of our Restated Certificate of Incorporation (as amended, the “Certificate

March 6, 2025 EX-10.17

Form of Performance-Based Restricted Stock Unit Agreement

Exhibit 10.17 OLD SECOND BANCORP, INC. 2019 EQUITY INCENTIVE PLAN, AS AMENDED AND RESTATED PERFORMANCE-BASED RESTRICTED STOCK UNIT AGREEMENT The Participant specified below has been granted a restricted stock unit award (the “Award”) by Old Second Bancorp, Inc., a Delaware corporation (the “Company”), under the Old Second Bancorp, Inc. 2019 Equity Incentive Plan, As Amended and Restated (the “Plan

February 26, 2025 425

Transcript of Old Second Bancorp, Inc.’s Investor Call on February 25, 2025 Related to the Proposed Business Combination with Bancorp Financial, Inc.

Filed by Old Second Bancorp, Inc. pursuant to Rule 425 under the Securities Act of 1933 and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934 Subject Company: Bancorp Financial, Inc. Filer’s Commission File No.: 000-10537 Date: February 26, 2025 Transcript of Old Second Bancorp, Inc.’s Investor Call on February 25, 2025 Related to the Proposed Business Combination with

February 25, 2025 425

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 (Date of earliest event reported): February 24, 2025 (Exact name of

I 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 (Date of earliest event reported): February 24, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S

February 25, 2025 EX-2.1

Agreement and Plan of Merger between Old Second Bancorp, Inc. and Bancorp Financial, Inc. dated as of February 24, 2025+

Exhibit 2.1 Execution Version AGREEMENT AND PLAN OF MERGER by and between OlD Second Bancorp, INc. and BANCORP FINANCIAL, INC. Dated as of February 24, 2025 Table of Contents Page Article 1 THE MERGER‌2 1.1 Merger.‌2 1.2 Time and Place of Closing.‌2 1.3 Effective Time.‌2 1.4 Charter of Surviving Entity.‌2 1.5 Bylaws of Surviving Entity.‌2 1.6 Directors and Officers.‌2 1.7 Bank Merger.‌3 1.8 Tax Tr

February 25, 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 (Date of earliest event reported): February 24, 2025 (Exact name of

I 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 (Date of earliest event reported): February 24, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S

February 25, 2025 EX-99.1

Old Second and Evergreen Bank Group Announce Strategic Combination

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, February 25, 2025 Chief Operating Officer and Chief Financial Officer (630) 906-5484 Old Second and Evergreen Bank Group Announce Strategic Combination AURORA and OAK BROOK, Illinois February 25, 2025 (PRNewswire) - Old Second Bancorp, Inc. (Nasdaq: OSBC) (“Old Second”) and Bancorp Financial, Inc.

February 25, 2025 EX-99.2

Exhibit 99.2

Exhibit 99.2

February 25, 2025 EX-99.1

Old Second and Evergreen Bank Group Announce Strategic Combination

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, February 25, 2025 Chief Operating Officer and Chief Financial Officer (630) 906-5484 Old Second and Evergreen Bank Group Announce Strategic Combination AURORA and OAK BROOK, Illinois February 25, 2025 (PRNewswire) - Old Second Bancorp, Inc. (Nasdaq: OSBC) (“Old Second”) and Bancorp Financial, Inc.

February 25, 2025 EX-99.2

Exhibit 99.2

Exhibit 99.2

February 25, 2025 EX-2.1

Agreement and Plan of Merger between Old Second Bancorp, Inc. and Bancorp Financial, Inc. dated as of February 24, 2025 (incorporated by reference to Exhibit 2.1 of the Old Second Bancorp, Inc. Current Report on Form 8-K filed on February 25, 2025)

Exhibit 2.1 Execution Version AGREEMENT AND PLAN OF MERGER by and between OlD Second Bancorp, INc. and BANCORP FINANCIAL, INC. Dated as of February 24, 2025 Table of Contents Page Article 1 THE MERGER‌2 1.1 Merger.‌2 1.2 Time and Place of Closing.‌2 1.3 Effective Time.‌2 1.4 Charter of Surviving Entity.‌2 1.5 Bylaws of Surviving Entity.‌2 1.6 Directors and Officers.‌2 1.7 Bank Merger.‌3 1.8 Tax Tr

January 22, 2025 EX-99.2

Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020

Exhibit 99.2 Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020 Loan Portfolio Composition Loan Portfolio Characteristics Balance Outstanding (000’s) $2,052,336 Total Commitment (000’s) $2,539,355 Average Loan Commitment $352,024 Number of Payment Deferrals /Modifications 449 Payment Modification Rate (% of Total Commitment)* 9.03% Loan Portfolio Characteristics • Lending focu

January 22, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

I 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 (Date of earliest event reported): January 22, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

January 22, 2025 EX-99.1

Old Second Bancorp, Inc. Reports Fourth Quarter 2024 Net Income of $19.1 Million, or $0.42 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer January 22, 2025 (630) 906-5484 Old Second Bancorp, Inc. Reports Fourth Quarter 2024 Net Income of $19.1 Million, or $0.42 per Diluted Share AURORA, IL, January 22, 2025 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second Na

January 21, 2025 8-K

Current Report

I 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 (Date of earliest event reported): January 21, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

January 2, 2025 8-K

Current Report

I 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 (Date of earliest event reported): January 2, 2025 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

December 20, 2024 8-K/A

Other Events

I United States Securities And Exchange Commission Washington, D.C. 20549 FORM 8-K/A (AMENDMENT NO. 1) Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 17, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission

December 17, 2024 8-K

Other Events

I 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 (Date of earliest event reported): December 17, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S

December 9, 2024 EX-99

OLD SECOND BANCORP, INC. ANNOUNCES COMPLETION OF CHICAGOLAND BRANCH TRANSACTION Old Second National Bank Completes Acquisition of Five Illinois Branches from First Merchants Bank

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, December 6, 2024 Chief Operating Officer and Chief Financial Officer (630) 906-5484 OLD SECOND BANCORP, INC. ANNOUNCES COMPLETION OF CHICAGOLAND BRANCH TRANSACTION Old Second National Bank Completes Acquisition of Five Illinois Branches from First Merchants Bank CHICAGO, IL-(December 6, 2024) - Old

December 9, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

I 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 (Date of earliest event reported): December 6, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

November 7, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

October 16, 2024 EX-99.2

Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020

Exhibit 99.2 Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020 Loan Portfolio Composition Loan Portfolio Characteristics Balance Outstanding (000’s) $2,052,336 Total Commitment (000’s) $2,539,355 Average Loan Commitment $352,024 Number of Payment Deferrals /Modifications 449 Payment Modification Rate (% of Total Commitment)* 9.03% Loan Portfolio Characteristics • Lending focu

October 16, 2024 EX-99.1

Old Second Bancorp, Inc. Reports Third Quarter 2024 Net Income of $23.0 Million, or $0.50 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer October 16, 2024 (630) 906-5484 Old Second Bancorp, Inc. Reports Third Quarter 2024 Net Income of $23.0 Million, or $0.50 per Diluted Share AURORA, IL, October 16, 2024 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second Nat

October 16, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

I 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 (Date of earliest event reported): October 16, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

October 15, 2024 8-K

Current Report

I 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 (Date of earliest event reported): October 15, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

October 1, 2024 8-K

Current Report

I 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 (Date of earliest event reported): October 1, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

August 27, 2024 EX-99.2

Exhibit 99.2

Exhibit 99.2

August 27, 2024 EX-99.1

OLD SECOND BANCORP, INC. AND FIRST MERCHANTS CORPORATION ANNOUNCE TRANSACTION INVOLVING CHICAGOLAND BRANCH OPERATIONS Old Second National Bank Acquires 5 Illinois Branches from First Merchants Bank Proposed Acquisition to Add $304 Million in Deposits

Exhibit 99.1 OLD SECOND BANCORP, INC. AND FIRST MERCHANTS CORPORATION ANNOUNCE TRANSACTION INVOLVING CHICAGOLAND BRANCH OPERATIONS Old Second National Bank Acquires 5 Illinois Branches from First Merchants Bank Proposed Acquisition to Add $304 Million in Deposits and $12 million in loans CHICAGO, IL-(August 27, 2024)—Old Second Bancorp, Inc. (“Old Second Bancorp”) (NASDAQ: OSBC), the parent compan

August 27, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

I 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 (Date of earliest event reported): August 26, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

August 8, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

July 17, 2024 EX-99.1

Old Second Bancorp, Inc. Reports Second Quarter 2024 Net Income of $21.9 Million, or $0.48 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer July 17, 2024 (630) 906-5484 Old Second Bancorp, Inc. Reports Second Quarter 2024 Net Income of $21.9 Million, or $0.48 per Diluted Share AURORA, IL, July 17, 2024 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second National

July 17, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

I 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 (Date of earliest event reported): July 17, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

July 17, 2024 EX-99.2

Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020

Exhibit 99.2 Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020 Loan Portfolio Composition Loan Portfolio Characteristics Balance Outstanding (000’s) $2,052,336 Total Commitment (000’s) $2,539,355 Average Loan Commitment $352,024 Number of Payment Deferrals /Modifications 449 Payment Modification Rate (% of Total Commitment)* 9.03% Loan Portfolio Characteristics • Lending focu

July 16, 2024 8-K

Current Report

I 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 (Date of earliest event reported): July 16, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

July 1, 2024 8-K

Current Report

I 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 (Date of earliest event reported): July 1, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

June 28, 2024 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 11-K ANNUAL REPORT Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the

I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 11-K ANNUAL REPORT Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR oTRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period

May 23, 2024 8-K

Submission of Matters to a Vote of Security Holders

I 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 (Date of earliest event reported): May 21, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 21, 2024 EX-99

Old Second Bancorp, Inc. Annual Stockholders Meeting

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, May 21, 2024 Chief Operating Officer and Chief Financial Officer (630) 906-5484 Old Second Bancorp, Inc. Annual Stockholders Meeting AURORA, IL, – Old Second Bancorp, Inc. (“Old Second”) (NASDAQ: OSBC), announced the Annual Stockholders Meeting will be held on May 21, 2024 at 9:00 am CDT. Sharehold

May 21, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

I 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 (Date of earliest event reported): May 21, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 9, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

May 8, 2024 EX-99

Old Second Bancorp, Inc. Investor Presentation

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, May 8, 2024 Chief Operating Officer and Chief Financial Officer (630) 906-5484 Old Second Bancorp, Inc. Investor Presentation AURORA, IL, – Old Second Bancorp, Inc. (“Old Second”) (NASDAQ: OSBC) announced the Company’s management is scheduled to attend the D.A. Davidson 26th Annual Financial Instit

May 8, 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 (Date of earliest event reported): May 8, 2024 (Exact name of regist

I 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 (Date of earliest event reported): May 8, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Empl

April 19, 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 (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)) ⌧ Defin

April 17, 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 (Date of earliest event reported): April 17, 2024 (Exact name of reg

I 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 (Date of earliest event reported): April 17, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. E

April 17, 2024 EX-99.2

Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020

Exhibit 99.2 Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020 Loan Portfolio Composition Loan Portfolio Characteristics Balance Outstanding (000’s) $2,052,336 Total Commitment (000’s) $2,539,355 Average Loan Commitment $352,024 Number of Payment Deferrals /Modifications 449 Payment Modification Rate (% of Total Commitment)* 9.03% Loan Portfolio Characteristics • Lending focu

April 17, 2024 EX-99.1

Old Second Bancorp, Inc. Reports First Quarter 2024 Net Income of $21.3 Million, or $0.47 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer April 17, 2024 (630) 906-5484 Old Second Bancorp, Inc. Reports First Quarter 2024 Net Income of $21.3 Million, or $0.47 per Diluted Share AURORA, IL, April 17, 2024 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second Nationa

April 16, 2024 8-K

Current Report

I 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 (Date of earliest event reported): April 16, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. E

April 1, 2024 8-K

Current Report

I 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 (Date of earliest event reported): April 1, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

March 26, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

I 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 (Date of earliest event reported): March 20, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. E

March 26, 2024 EX-10

Employment Agreement between Mr. Gary Collins and Old Second Bancorp, Inc. dated March 20, 2024.

Exhibit 10.1 EXECUTIVE EMPLOYMENT AGREEMENT This Employment Agreement (the “Agreement”) is entered into effective as of March 19, 2024 (“Effective Date”), by and between Old Second Bancorp, Inc. (the “Company”) and Gary Collins (the “Executive”). RECITALS WHEREAS, the Company and its wholly-owned subsidiary, Old Second National Bank (the “Bank”) are presently engaged in the general business of pro

March 7, 2024 EX-97

Old Second Bancorp, Inc. Clawback Policy dated August 15, 2023.

Exhibit 97 OLD SECOND BANCORP, INC. Incentive Compensation Recovery Policy (the “Policy”) A. Mandatory Clawback for Section 16 Officers. 1.Recovery of Excess Incentive Compensation. If Old Second Bancorp, Inc. (the “Company”) is required to prepare a Restatement, the Company’s board of directors (the “Board”) shall, unless the Board’s Compensation Committee (the “Compensation Committee”) determine

March 7, 2024 EX-4.5

Description of Capital Stock.

Exhibit 4.5 DESCRIPTION OF OLD SECOND BANCORP, INC. CAPITAL STOCK References to “we,” “us” or “our” and the “Company” herein refer to Old Second Bancorp, Inc., a Delaware corporation. This summary does not purport to be complete and is subject to and is qualified in its entirety by reference to our the applicable provisions of our Restated Certificate of Incorporation (as amended, the “Certificate

March 7, 2024 EX-21.1

A list of all subsidiaries of the Company.

Exhibit 21.1 LIST OF SUBSIDIARIES Subsidiaries of the Company Incorporated Under Laws of Percent Owned by the Company Old Second National Bank United States 100% of the common stock Old Second Capital Trust II State of Delaware 100% of the common stock Old Second Affordable Housing Fund, L.L.C. State of Illinois Owned by Old Second National Bank Station I, LLC State of Illinois Owned by Old Second

March 7, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ⌧ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ◻ 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 000-10537 (Exact n

February 13, 2024 SC 13G

OSBC / Old Second Bancorp, Inc. / VANGUARD GROUP INC - SCHEDULE 13G Passive Investment

SC 13G 1 tv01600-oldsecondbancorpinc.htm SCHEDULE 13G SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 Name of issuer: Old Second Bancorp Inc Title of Class of Securities: Common Stock CUSIP Number: 680277100 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appropriate box to designate the rule pursua

February 8, 2024 SC 13G/A

OSBC / Old Second Bancorp, Inc. / FJ Capital Management LLC Passive Investment

SC 13G/A 1 eps11128osbc.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4) * Old Second Bancorp, Inc. (OSBC) (Name of Issuer) Common Stock (Title of Class of Securities) 680277100 (CUSIP Number) 12/31/2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate t

January 24, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

I 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 (Date of earliest event reported): January 24, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

January 24, 2024 EX-99.1

Old Second Bancorp, Inc. Reports Fourth Quarter 2023 Net Income of $18.2 Million, or $0.40 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer January 24, 2024 (630) 906-5484 Old Second Bancorp, Inc. Reports Fourth Quarter 2023 Net Income of $18.2 Million, or $0.40 per Diluted Share AURORA, IL, January 24, 2024 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second Na

January 24, 2024 EX-99.2

Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020

Exhibit 99.2 Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020 Loan Portfolio Composition Loan Portfolio Characteristics Balance Outstanding (000’s) $2,052,336 Total Commitment (000’s) $2,539,355 Average Loan Commitment $352,024 Number of Payment Deferrals /Modifications 449 Payment Modification Rate (% of Total Commitment)* 9.03% Loan Portfolio Characteristics • Lending focu

January 16, 2024 8-K

Current Report

I 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 (Date of earliest event reported): January 16, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

January 3, 2024 8-K

Other Events

I 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 (Date of earliest event reported): January 3, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

January 2, 2024 8-K

Current Report

I 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 (Date of earliest event reported): January 2, 2024 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

November 8, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

October 27, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

I 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 (Date of earliest event reported): October 27, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

October 18, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

I 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 (Date of earliest event reported): October 18, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

October 18, 2023 EX-99.1

Old Second Bancorp, Inc. Reports Third Quarter 2023 Net Income of $24.3 Million, or $0.54 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer October 18, 2023 (630) 906-5484 Old Second Bancorp, Inc. Reports Third Quarter 2023 Net Income of $24.3 Million, or $0.54 per Diluted Share AURORA, IL, October 18, 2023 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second Nat

October 18, 2023 EX-99.2

Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020

Exhibit 99.2 Old Second Bancorp, Inc. Loan Portfolio Disclosures As of June 30, 2020 Loan Portfolio Composition Loan Portfolio Characteristics Balance Outstanding (000’s) $2,052,336 Total Commitment (000’s) $2,539,355 Average Loan Commitment $352,024 Number of Payment Deferrals /Modifications 449 Payment Modification Rate (% of Total Commitment)* 9.03% Loan Portfolio Characteristics • Lending focu

October 17, 2023 8-K

Current Report

I 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 (Date of earliest event reported): October 17, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

October 2, 2023 8-K

Current Report

I 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 (Date of earliest event reported): October 2, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

September 11, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

I 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 (Date of earliest event reported): September 8, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S

August 24, 2023 CORRESP

Old Second Bancorp, Inc. 37 South River Street Aurora, Illinois 60507 (630) 892-0202 August 24, 2023

Old Second Bancorp, Inc. 37 South River Street Aurora, Illinois 60507 (630) 892-0202 August 24, 2023 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, D.C. 20549 Attention: Aisha Adegbuyi Re: Old Second Bancorp, Inc. (the “Company”) Request for Acceleration of Effectiveness of Form S-3 SEC File No. 333-274068 (the “Registration

August 24, 2023 S-3/A

As filed with the Securities and Exchange Commission on August 24, 2023.

As filed with the Securities and Exchange Commission on August 24, 2023. Registration No. 333-274068 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 1 TO FORM S-3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 OLD SECOND BANCORP, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organ

August 24, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables FORM S-3 (Form Type) OLD SECOND BANCORP, INC.

August 24, 2023 EX-4

Form of Indenture.

Exhibit 4.8 OLD SECOND BANCORP, INC., as Issuer and [ ], as Trustee INDENTURE Dated as of , 20 CROSS REFERENCE SHEET* Provisions of Trust Indenture Act of 1939, as amended, and Indenture to be dated as of , 20 by and between Old Second Bancorp, Inc. and [ ], as Trustee: Section of the Trust Indenture Act Section of Indenture 310(a)(1), (2) and (5) 6.09 310(a)(3) and (4) Inapplicable 310(b) 6.08 an

August 18, 2023 EX-4.8

Form of Indenture.

Exhibit 4.8 OLD SECOND BANCORP, INC., as Issuer and [ ], as Trustee INDENTURE Dated as of , 20 CROSS REFERENCE SHEET* Provisions of Trust Indenture Act of 1939, as amended, and Indenture to be dated as of , 20 by and between Old Second Bancorp, Inc. and [ ], as Trustee: Section of the Trust Indenture Act Section of Indenture 310(a)(1), (2) and (5) 6.09 310(a)(3) and (4) Inapplicable 310(b) 6.08 an

August 18, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables FORM S-3 (Form Type) OLD SECOND BANCORP, INC.

August 18, 2023 S-3

As filed with the Securities and Exchange Commission on August 18, 2023.

As filed with the Securities and Exchange Commission on August 18, 2023. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 OLD SECOND BANCORP, INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 36-3143493 (I.R.

August 15, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

I 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 (Date of earliest event reported): August 15, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

August 8, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

August 7, 2023 EX-99

Old Second Bancorp, Inc. Investor Presentation

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, Chief Financial Officer August 7, 2023 (630) 906-5484 Old Second Bancorp, Inc. Investor Presentation AURORA, IL, – Old Second Bancorp, Inc. (“Old Second”) (NASDAQ: OSBC) announced the Company’s management is scheduled to attend the Keefe, Bruyette & Woods Community Bank Investor Conference on Augus

August 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 (Date of earliest event reported): August 7, 2023 (Exact name of reg

I 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 (Date of earliest event reported): August 7, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. E

July 19, 2023 EX-99

Old Second Bancorp, Inc. Reports Second Quarter 2023 Net Income of $25.6 Million, or $0.56 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer July 19, 2023 (630) 906-5484 Old Second Bancorp, Inc. Reports Second Quarter 2023 Net Income of $25.6 Million, or $0.56 per Diluted Share AURORA, IL, July 19, 2023 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second National

July 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 (Date of earliest event reported): July 19, 2023 (Exact name of regi

I 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 (Date of earliest event reported): July 19, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

July 18, 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 (Date of earliest event reported): July 18, 2023 (Exact name of regi

I 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 (Date of earliest event reported): July 18, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

July 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 (Date of earliest event reported): July 12, 2023 (Exact name of regi

I 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 (Date of earliest event reported): July 12, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

July 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 (Date of earliest event reported): July 3, 2023 (Exact name of regis

I 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 (Date of earliest event reported): July 3, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

June 30, 2023 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 11-K ANNUAL REPORT Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the

I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 11-K ANNUAL REPORT Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR oTRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period

May 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 (Date of earliest event reported): May 25, 2023 (Exact name of regis

I 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 (Date of earliest event reported): May 25, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 24, 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 (Date of earliest event reported): May 23, 2023 (Exact name of regis

I 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 (Date of earliest event reported): May 23, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 23, 2023 EX-99

Old Second Bancorp, Inc. Annual Stockholders Meeting

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, Chief Financial Officer May 23, 2023 (630) 906-5484 Old Second Bancorp, Inc. Annual Stockholders Meeting AURORA, IL, – Old Second Bancorp, Inc. (“Old Second”) (NASDAQ: OSBC), announced the Annual Stockholders Meeting will be held on May 23, 2023 at 9:00 am CDT. Shareholders and investors may access

May 23, 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 (Date of earliest event reported): May 23, 2023 (Exact name of regis

I 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 (Date of earliest event reported): May 23, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 15, 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 (Date of earliest event reported): May 15, 2023 (Exact name of regis

I 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 (Date of earliest event reported): May 15, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Emp

May 15, 2023 EX-99

Old Second Bancorp, Inc. Investor Presentation

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Executive Vice President, Chief Financial Officer May 15, 2023 (630) 906-5484 Old Second Bancorp, Inc. Investor Presentation AURORA, IL, – Old Second Bancorp, Inc. (“Old Second”) (NASDAQ: OSBC), announced: ● The Company’s management is scheduled to attend the D.A. Davidson 25th Annual Financial Institutions Conference on Ma

May 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

April 19, 2023 EX-99

Old Second Bancorp, Inc. Reports First Quarter 2023 Net Income of $23.6 Million, or $0.52 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer April 19, 2023 (630) 906-5484 Old Second Bancorp, Inc. Reports First Quarter 2023 Net Income of $23.6 Million, or $0.52 per Diluted Share AURORA, IL, April 19, 2023 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second Nationa

April 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 (Date of earliest event reported): April 19, 2023 (Exact name of reg

I 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 (Date of earliest event reported): April 19, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. E

April 18, 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 (Date of earliest event reported): April 18, 2023 (Exact name of reg

I 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 (Date of earliest event reported): April 18, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. E

April 14, 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)) ⌧ Defin

April 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 (Date of earliest event reported): April 3, 2023 (Exact name of regi

I 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 (Date of earliest event reported): April 3, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Em

March 9, 2023 EX-4.5

Description of the Company’s Securities Registered Pursuant to Section 12 of the Securities Exchange Act of 1934 (incorporated by reference to Exhibit 4.5 of the Company’s Annual Report on Form 10-K filed on March 9, 2023).

Exhibit 4.5 DESCRIPTION OF OLD SECOND BANCORP, INC. CAPITAL STOCK References to “we,” “us” or “our” and the “Company” herein refer to Old Second Bancorp, Inc., a Delaware corporation. This summary does not purport to be complete and is subject to and is qualified in its entirety by reference to our the applicable provisions of our Restated Certificate of Incorporation (as amended, the “Certificate

March 9, 2023 EX-21.1

A list of all subsidiaries of the Company.

Exhibit 21.1 LIST OF SUBSIDIARIES Subsidiaries of the Company Incorporated Under Laws of Percent Owned by the Company Old Second National Bank United States 100% of the common stock Old Second Capital Trust II State of Delaware 100% of the common stock Old Second Affordable Housing Fund, L.L.C. State of Illinois Owned by Old Second National Bank Station I, LLC State of Illinois Owned by Old Second

March 9, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ⌧ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ◻ 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 000-10537 (Exact n

February 8, 2023 SC 13G/A

OSBC / Old Second Bancorp Inc / FJ Capital Management LLC Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3) * Old Second Bancorp, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 680277100 (CUSIP Number) 12/31/2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Sche

January 25, 2023 EX-99

Old Second Bancorp, Inc. Reports Fourth Quarter 2022 Net Income of $23.6 Million, or $0.52 per Diluted Share

(NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer January 25, 2023 (630) 906-5484 Old Second Bancorp, Inc. Reports Fourth Quarter 2022 Net Income of $23.6 Million, or $0.52 per Diluted Share AURORA, IL, January 25, 2023 – Old Second Bancorp, Inc. (the “Company,” “Old Second,” “we,” “us,” and “our”) (NASDAQ: OSBC), the parent company of Old Second Na

January 25, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

I 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 (Date of earliest event reported): January 25, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

January 17, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Other Events

I 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 (Date of earliest event reported): January 13, 2023 (Exact name of registrant as specified in its charter) Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S.

January 3, 2023 8-K

Current Report

? I ? 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 (Date of earliest event reported): January 3, 2023 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numb

November 8, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

October 27, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

? I ? 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 (Date of earliest event reported): October 25, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File N

October 26, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

? I ? 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 (Date of earliest event reported): October 26, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numbe

October 26, 2022 EX-99

Old Second Bancorp, Inc. Reports Third Quarter 2022 Net Income of $19.5 Million, or $0.43 per Diluted Share

? ? ? ? ? ? ? ? ? ? ? (NASDAQ:OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer October 26, 2022 ? (630) 906-5484 ? ? ? ? Old Second Bancorp, Inc. Reports Third Quarter 2022 Net Income of $19.5 Million, or $0.43 per Diluted Share ? AURORA, IL, October 26, 2022 ? Old Second Bancorp, Inc. (the ?Company,? ?Old Second,? ?we,? ?us,? and ?our?) (NASDAQ: O

October 18, 2022 8-K

Current Report

? I ? 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 (Date of earliest event reported): October 18, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Num

October 3, 2022 8-K

Current Report

? I ? 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 (Date of earliest event reported): October 3, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numb

August 8, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

July 27, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

? I ? 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 (Date of earliest event reported): July 27, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number)

July 27, 2022 EX-99

Old Second Bancorp, Inc. Reports Second Quarter 2022 Net Income of $12.2 Million, or $0.27 per Diluted Share

? ? ? ? ? ? ? ? ? ? ? (NASDAQ:OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer July 27, 2022 ? (630) 906-5484 ? ? ? ? Old Second Bancorp, Inc. Reports Second Quarter 2022 Net Income of $12.2 Million, or $0.27 per Diluted Share ? AURORA, IL, July 27, 2022 ? Old Second Bancorp, Inc. (the ?Company,? ?Old Second,? ?we,? ?us,? and ?our?) (NASDAQ: OSBC),

July 19, 2022 8-K

Current Report

? I ? 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 (Date of earliest event reported): July 19, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number

July 1, 2022 8-K

Current Report

? I ? 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 (Date of earliest event reported): July 1, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number)

June 30, 2022 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 11-K ANNUAL REPORT Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the

I ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? Form 11-K ? ANNUAL REPORT ? Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 ? xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the fiscal year ended December 31, 2021 ? OR ? oTRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the

May 18, 2022 8-K

Other Events, Submission of Matters to a Vote of Security Holders

? I ? 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 (Date of earliest event reported): May 17, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numbe

May 17, 2022 EX-99.1

Old Second Bancorp, Inc. Annual Stockholders Meeting

? ? ? ? ? ? ? ? ? ? ? (NASDAQ:OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Executive Vice President, Chief Financial Officer May 17, 2022 ? (630) 906-5484 ? ? ? ? ? Old Second Bancorp, Inc. Annual Stockholders Meeting ? AURORA, IL, ? Old Second Bancorp, Inc. (?Old Second?) (NASDAQ: OSBC), announced the Annual Stockholders Meeting will be held on May 17, 2022 at 9:00 a

May 17, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

? I ? 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 (Date of earliest event reported): May 17, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numbe

May 9, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

April 27, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

? I ? 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 (Date of earliest event reported): April 27, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number)

April 27, 2022 EX-99.1

Old Second Bancorp, Inc. Reports First Quarter 2022 Net Income of $12.0 Million, or $0.27 per Diluted Share

? ? ? ? ? ? ? ? ? ? ? (NASDAQ:OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer April 27, 2022 ? (630) 906-5484 ? ? ? ? Old Second Bancorp, Inc. Reports First Quarter 2022 Net Income of $12.0 Million, or $0.27 per Diluted Share ? AURORA, IL, April 27, 2022 ? Old Second Bancorp, Inc. (the ?Company,? ?Old Second,? ?we,? ?us,? and ?our?) (NASDAQ: OSBC)

April 20, 2022 8-K/A

Other Events

? I ? United States Securities And Exchange Commission Washington, D.C. 20549 ? FORM 8-K/A (Amendment No.1) ? Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 19, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (

April 19, 2022 8-K

Current Report

? I ? 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 (Date of earliest event reported): April 19, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numbe

April 14, 2022 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)) ?

April 1, 2022 8-K

Current Report

? I ? 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 (Date of earliest event reported): April 1, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number

March 10, 2022 EX-4.5

Description of Capital Stock.

Exhibit 4.5 DESCRIPTION OF OLD SECOND BANCORP, INC. CAPITAL STOCK ? References to ?we,? ?us? or ?our? and the ?Company? herein refer to Old Second Bancorp, Inc., a Delaware corporation. ? This summary does not purport to be complete and is subject to and is qualified in its entirety by reference to our the applicable provisions of our Restated Certificate of Incorporation (as amended, the ?Certifi

March 10, 2022 EX-21.1

A list of all subsidiaries of the Company.

Exhibit 21.1 ? ? LIST OF SUBSIDIARIES ? ? ? ? ? ? ? ? Subsidiaries of the Company ? Incorporated Under Laws of ? Percent Owned by the Company Old Second National Bank ? United States ? 100% of the common stock Old Second Capital Trust II ? State of Delaware ? 100% of the common stock Old Second Affordable Housing Fund, L.L.C. ? State of Illinois ? Owned by Old Second National Bank Station I, LLC ?

March 10, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

February 16, 2022 EX-99.4

UNAUDITED PRO FORMA CONDENSED COMBINED CONSOLIDATED FINANCIAL INFORMATION

Exhibit 99.4 UNAUDITED PRO FORMA CONDENSED COMBINED CONSOLIDATED FINANCIAL INFORMATION The following tables show the condensed combined financial information for each of Old Second Bancorp, Inc. (“Old Second”) and West Suburban Bancorp, Inc. (“West Suburban”), as well as unaudited pro forma condensed combined financial information for Old Second and West Suburban reflecting the merger as of and fo

February 16, 2022 EX-99.2

INDEX TO FINANCIAL STATEMENTS West Suburban Bancorp, Inc. and Subsidiaries – Unaudited Consolidated Financial Statements for the Nine Months Ended September 30, 2021 and 2020

Exhibit 99.2 INDEX TO FINANCIAL STATEMENTS West Suburban Bancorp, Inc. and Subsidiaries – Unaudited Consolidated Financial Statements for the Nine Months Ended September 30, 2021 and 2020 Unaudited Consolidated Balance Sheets as of September 30, 2021 and December 31, 2020 2 Unaudited Consolidated Statements of Income for the nine months ended September 30, 2021 and 2020 3 Unaudited Consolidated St

February 16, 2022 8-K/A

Financial Statements and Exhibits

? I ? United States Securities And Exchange Commission Washington, D.C. 20549 ? FORM 8-K/A (Amendment No. 1) Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 1, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation)

February 15, 2022 144

INSTRUCTION: The person filing this notice should contact the issuer to obtain the I.R.S. Identification Number and the S.E.C. File Number.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933 OMB APPROVAL OMB Number: 3235-0101 Expires: May 31, 2017 Estimated average burden hours per response . . . . . . . . . 1.00 SEC USE ONLY DOCUMENT SEQUENCE NO. CUSIP NUMBER ATTENTION: Transmit for filing 3 copies of this form co

February 15, 2022 144

INSTRUCTION: The person filing this notice should contact the issuer to obtain the I.R.S. Identification Number and the S.E.C. File Number.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933 OMB APPROVAL OMB Number: 3235-0101 Expires: May 31, 2017 Estimated average burden hours per response . . . . . . . . . 1.00 SEC USE ONLY DOCUMENT SEQUENCE NO. CUSIP NUMBER ATTENTION: Transmit for filing 3 copies of this form co

February 15, 2022 144

INSTRUCTION: The person filing this notice should contact the issuer to obtain the I.R.S. Identification Number and the S.E.C. File Number.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933 OMB APPROVAL OMB Number: 3235-0101 Expires: May 31, 2017 Estimated average burden hours per response . . . . . . . . . 1.00 SEC USE ONLY DOCUMENT SEQUENCE NO. CUSIP NUMBER ATTENTION: Transmit for filing 3 copies of this form co

February 11, 2022 SC 13G/A

OSBC / Old Second Bancorp Inc / FJ Capital Management LLC Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2) * Old Second Bancorp, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 680277100 (CUSIP Number) 12/31/2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Sche

February 10, 2022 SC 13G/A

OSBC / Old Second Bancorp Inc / BANC FUNDS CO LLC - NONE Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Old Second Bancorp, Inc. (Name of Issuer) COMMON STOCK (Title of Class of Securities) 680277100 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which thi

January 26, 2022 EX-99.1

Old Second Bancorp, Inc. Reports Fourth Quarter 2021 Financial Results

? ? ? ? ? ? ? ? ? ? ? (NASDAQ: OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer January 26, 2022 ? (630) 906-5484 ? ? ? ? Old Second Bancorp, Inc. Reports Fourth Quarter 2021 Financial Results ? AURORA, IL, January 26, 2022 ? Old Second Bancorp, Inc. (the ?Company,? ?Old Second,? ?we,? ?us,? and ?our?) (NASDAQ: OSBC), the parent company of Old Seco

January 26, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

? I ? 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 (Date of earliest event reported): January 26, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numbe

January 18, 2022 8-K

Other Events

? I ? 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 (Date of earliest event reported): January 18, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File N

January 3, 2022 8-K

Current Report

? I ? 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 (Date of earliest event reported): January 3, 2022 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numb

December 1, 2021 EX-10.1

Employment Agreement, dated July 25, 2021, between Old Second Bancorp, Inc. and Keith Acker.

?Exhibit 10.1 ?Execution Copy EXECUTIVE EMPLOYMENT AGREEMENT This Employment Agreement (the ?Agreement?) is entered into as of July 25, 2021 (?Effective Date?), by and between Old Second Bancorp, Inc. (the ?Company? or ?Bank?) and Keith W. Acker (the ?Executive?). RECITALS WHEREAS, the Bank is presently engaged in the general business of providing community banking and trust business services. The

December 1, 2021 EX-99.1

Old Second Completes Merger with West Suburban

?Exhibit 99.1 ? ? ? ? ? ? ? ? ? ? (NASDAQ:OSBC) ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer December 1, 2021 ? (630) 906-5484 ? ? Old Second Completes Merger with West Suburban AURORA, Illinois December 1, 2021 (PRNewswire) ? Old Second Bancorp, Inc. (Nasdaq: OSBC) (?Old Second?) announced today that it has completed its previously announced merger with West Sub

December 1, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets, Other Events

? I ? 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 (Date of earliest event reported): December 1, 2021 (December 1, 2021) (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation)

November 30, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

? I ? 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 (Date of earliest event reported): November 30, 2021 (November 30, 2021) (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporatio

November 30, 2021 EX-99.1

Old Second and West Suburban Announce Shareholder Approval of Merger

?Exhibit 99.1 ? Old Second and West Suburban Announce Shareholder Approval of Merger ? AURORA and LOMBARD, Illinois November 30, 2021 (PRNewswire) ? Old Second Bancorp, Inc. (Nasdaq: OSBC) (?Old Second?) and West Suburban Bancorp, Inc. (?West Suburban?) jointly announced today that each has received shareholder approval for the merger of West Suburban into Old Second in a cash and stock transactio

November 5, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

October 25, 2021 424B3

MERGER PROPOSED — YOUR VOTE IS VERY IMPORTANT

TABLE OF CONTENTS ?Filed Pursuant to Rule 424(b)(3) ?Registration No. 333-259964? ? ? ? ? MERGER PROPOSED???YOUR VOTE IS VERY IMPORTANT To the Shareholders of Old Second Bancorp, Inc. and West Suburban Bancorp, Inc.: On July 25, 2021, Old Second Bancorp, Inc., which we refer to as ?Old Second,? and West Suburban Bancorp, Inc., which we refer to as ?West Suburban,? entered into an Agreement and Pla

October 21, 2021 EX-99.2

99.2 Loan Portfolio Disclosures for Old Second Bancorp, Inc. dated October 20, 2021

?Exhibit 99.2 ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ??

October 21, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

? I ? 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 (Date of earliest event reported): October 20, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numbe

October 21, 2021 EX-99.1

Old Second Reports Third Quarter Net Income of $8.4 million, or $0.29 per Diluted Share

? ? ? ? ? ? ? ? ? ? ? (NASDAQ: OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer October 20, 2021 ? (630) 906-5484 ? ? ? ? Old Second Reports Third Quarter Net Income of $8.4 million, or $0.29 per Diluted Share ? AURORA, IL, October 20, 2021 ? Old Second Bancorp, Inc. (the ?Company,? ?Old Second,? ?we,? ?us,? and ?our?) (NASDAQ: OSBC), the parent co

October 21, 2021 425

Old Second Reports Third Quarter Net Income of $8.4 million, or $0.29 per Diluted Share

Filed by Old Second Bancorp, Inc. pursuant to Rule 425 under the Securities Act of 1933 and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934 Subject Company: West Suburban Bancorp, Inc. Filer?s Commission File No.: 000-10537 Date: October 20, 2021 Set forth below is the third quarter 2021 earnings release for Old Second Bancorp, Inc., which references the proposed mer

October 19, 2021 EX-99.1

Consent of Citigroup Global Markets Inc.*

Exhibit 99.1 Consent of Citigroup Global Markets Inc. We hereby consent to (1) the inclusion of our opinion letter, dated July 25, 2021, to the Board of Directors of Old Second Bancorp, Inc. (?Old Second?) as Annex B, (2) the description of such opinion letter and the references to our name under the captions entitled ?Summary?Opinion of Old Second?s Financial Advisor?, ?The Merger?Background of t

October 19, 2021 CORRESP

October 19, 2021

October 19, 2021 Via Edgar U.S. Securities and Exchange Commission Division of Corporation Finance Office of Finance Washington, D.C. 20549 Attention: Tonya K. Aldave Re: Request for Acceleration Old Second Bancorp, Inc. (the ?Registrant?) Registration Statement on Form S-4 (File No. 333-259964) Dear Sir or Madam: Pursuant to Rule 461 under the Securities Act of 1933, as amended (the ?Securities A

October 19, 2021 EX-99.7

Form of Proxy Card to be used by West Suburban.*

Exhibit 99.7 Signature [PLEASE SIGN WITHIN BOX] Date Signature (Joint Owners) Date TO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS FOLLOWS: KEEP THIS PORTION FOR YOUR RECORDS DETACH AND RETURN THIS PORTION ONLY THIS PROXY CARD IS VALID ONLY WHEN SIGNED AND DATED. D61349-TBD For Against Abstain ! ! ! ! ! ! WEST SUBURBAN BANCORP, INC. ATTN: GEORGE RANSTEAD 2800 S. FINLEY ROAD DOWNERS GROVE, 60515

October 19, 2021 S-4/A

As filed with the Securities and Exchange Commission on October 19, 2021

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on October 19, 2021 File No.

October 19, 2021 EX-99.2

Consent of Keefe, Bruyette & Woods, Inc.*

Exhibit 99.2 CONSENT OF KEEFE, BRUYETTE & WOODS, INC. We hereby consent to the inclusion of our opinion letter to the Board of Directors of West Suburban Bancorp, Inc. (?West Suburban?), as Annex C to the Joint Proxy Statement/Prospectus which forms a part of Amendment No. 1 to the Registration Statement on Form S-4 filed on the date hereof (the ?Amended Registration Statement?) relating to the pr

October 19, 2021 8-K

Current Report

? I ? 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 (Date of earliest event reported): October 19, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Num

October 19, 2021 EX-99.6

Form of Proxy Card to be used by Old Second.*

Exhibit 99.6 Signature [PLEASE SIGN WITHIN BOX] Date Signature (Joint Owners) Date TO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS FOLLOWS: KEEP THIS PORTION FOR YOUR RECORDS DETACH AND RETURN THIS PORTION ONLY THIS PROXY CARD IS VALID ONLY WHEN SIGNED AND DATED. D61326-S33867 1. To adopt the Agreement and Plan of Merger and Reorganization, dated as of July 25, 2021 (as it may be amended from t

October 15, 2021 425

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 (Date of earliest event reported): October 14, 2021 (October 14, 202

? I ? 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 (Date of earliest event reported): October 14, 2021 (October 14, 2021) (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation)

October 15, 2021 8-K

Financial Statements and Exhibits, Other Events

? I ? 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 (Date of earliest event reported): October 14, 2021 (October 14, 2021) (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation)

October 15, 2021 EX-99.1

Old Second Bancorp, Inc. Announces Receipt of Regulatory Approvals to Complete its Merger Transaction with West Suburban Bancorp, Inc.

? ? ? ? ? (NASDAQ: OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer October 14, 2021 ? (630) 906-5484 ? ? ? Old Second Bancorp, Inc. Announces Receipt of Regulatory Approvals to Complete its Merger Transaction with West Suburban Bancorp, Inc. ? Aurora, IL, October 14, 2021 - Aurora, IL-based Old Second Bancorp, Inc. (?Old Second?, NASDAQ: OSBC), th

October 15, 2021 EX-99.1

Old Second Bancorp, Inc. Announces Receipt of Regulatory Approvals to Complete its Merger Transaction with West Suburban Bancorp, Inc.

? ? ? ? ? (NASDAQ: OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer October 14, 2021 ? (630) 906-5484 ? ? ? Old Second Bancorp, Inc. Announces Receipt of Regulatory Approvals to Complete its Merger Transaction with West Suburban Bancorp, Inc. ? Aurora, IL, October 14, 2021 - Aurora, IL-based Old Second Bancorp, Inc. (?Old Second?, NASDAQ: OSBC), th

October 1, 2021 8-K

Current Report

? I ? 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 (Date of earliest event reported): October 1, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numb

October 1, 2021 EX-99.4

Consent of Keith Kotche to be named as director.*

Exhibit 99.4 CONSENT OF DIRECTOR-NOMINEE This Consent of Director-Nominee is delivered in connection with the registration statement on Form S-4 of Old Second Bancorp, Inc. to be filed with the Securities Exchange Commission (as it may be amended from time to time, the ?Registration Statement?) for the registration under the Securities Act of 1933, as amended, of the shares of Old Second Bancorp,

October 1, 2021 EX-99.1

Consent of Citigroup Global Markets Inc.*

Exhibit 99.1 Consent of Citigroup Global Markets Inc. We hereby consent to (1) the inclusion of our opinion letter, dated July 25, 2021, to the Board of Directors of Old Second Bancorp, Inc. (?Old Second?) as Annex B, (2) the description of such opinion letter and the references to our name under the captions entitled ?Summary?Opinion of Old Second?s Financial Advisor?, ?The Merger?Background of t

October 1, 2021 EX-99.3

Consent of Keith Acker to be named as director.*

Exhibit 99.3 CONSENT OF DIRECTOR-NOMINEE This Consent of Director-Nominee is delivered in connection with the registration statement on Form S-4 of Old Second Bancorp, Inc. to be filed with the Securities Exchange Commission (as it may be amended from time to time, the ?Registration Statement?) for the registration under the Securities Act of 1933, as amended, of the shares of Old Second Bancorp,

October 1, 2021 EX-99.2

Consent of Keefe, Bruyette & Woods, Inc.*

Exhibit 99.2 CONSENT OF KEEFE, BRUYETTE & WOODS, INC. We hereby consent to the inclusion of our opinion letter to the Board of Directors of West Suburban Bancorp, Inc. (?West Suburban?), as Annex C to the Joint Proxy Statement/Prospectus which forms a part of the Registration Statement on Form S-4 filed on the date hereof (the ?Registration Statement?) relating to the proposed merger of West Subur

October 1, 2021 S-4

Power of Attorney (included on signature page).**

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on October 1, 2021 File No.

October 1, 2021 EX-99.5

Consent of John Williams, Jr. to be named as director.*

Exhibit 99.5 CONSENT OF DIRECTOR-NOMINEE This Consent of Director-Nominee is delivered in connection with the registration statement on Form S-4 of Old Second Bancorp, Inc. to be filed with the Securities Exchange Commission (as it may be amended from time to time, the ?Registration Statement?) for the registration under the Securities Act of 1933, as amended, of the shares of Old Second Bancorp,

August 18, 2021 S-8

As filed with the Securities and Exchange Commission on August 18, 2021

As filed with the Securities and Exchange Commission on August 18, 2021 Registration No.

August 17, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

? I ? 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 (Date of earliest event reported): August 17, 2021 (August 17, 2021) (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (

August 6, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents I ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

July 27, 2021 425

Transcript of Old Second Bancorp, Inc.’s Investor Call on July 26, 2021 Related to the Proposed Business Combination with West Suburban Bancorp, Inc.

Filed by Old Second Bancorp, Inc. pursuant to Rule 425 under the Securities Act of 1933 and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934 Subject Company: West Suburban Bancorp, Inc. Filer’s Commission File No.: 000-10537 Date: July 27, 2021 Transcript of Old Second Bancorp, Inc.’s Investor Call on July 26, 2021 Related to the Proposed Business Combination with Wes

July 26, 2021 EX-99.2

Investor Presentation

Exhibit 99.2 ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

July 26, 2021 EX-99.1

Old Second and West Suburban Announce Combination to Create the Leading Community Bank in Chicago

? ? ? ? ? ? ? ? ? ? ? (NASDAQ:OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer July 26, 2021 ? (630) 906-5484 ? ? ? Old Second and West Suburban Announce Combination to Create the Leading Community Bank in Chicago ? AURORA and LOMBARD, Illinois July 26, 2021 (PRNewswire) - Old Second Bancorp, Inc. (Nasdaq: OSBC) (?Old Second?) and West Suburban Ban

July 26, 2021 EX-2.1

Agreement and Plan of Merger between Old Second Bancorp, Inc. and West Suburban Bancorp, Inc. dated as of July 25, 2021+

Exhibit 2.1 ? Execution Version ? ? ? ? ? ? ? ? ? ? ? AGREEMENT AND PLAN OF MERGER AND REORGANIZATION ? by and between ? OLD SECOND BANCORP, INC. ? and ? WEST SUBURBAN BANCORP, INC. ? ? Dated as of July 25, 2021 ? ? ? ? ? ? ? ? ? TABLE OF CONTENTS ? ? Page LIST OF EXHIBITS?iv AGREEMENT AND PLAN OF MERGER AND REORGANIZATION?1 ARTICLE 1 THE MERGER?2 1.1Merger.?2 1.2Time and Place of Closing.?2 1.3Ef

July 26, 2021 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

? I ? 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 (Date of earliest event reported): July 26, 2021 (July 25, 2021) (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Comm

July 26, 2021 EX-2.1

Agreement and Plan of Merger between Old Second Bancorp, Inc. and West Suburban Bancorp, Inc. dated as of July 25, 2021+

Exhibit 2.1 ? Execution Version ? ? ? ? ? ? ? ? ? ? ? AGREEMENT AND PLAN OF MERGER AND REORGANIZATION ? by and between ? OLD SECOND BANCORP, INC. ? and ? WEST SUBURBAN BANCORP, INC. ? ? Dated as of July 25, 2021 ? ? ? ? ? ? ? ? ? TABLE OF CONTENTS ? ? Page LIST OF EXHIBITS?iv AGREEMENT AND PLAN OF MERGER AND REORGANIZATION?1 ARTICLE 1 THE MERGER?2 1.1Merger.?2 1.2Time and Place of Closing.?2 1.3Ef

July 26, 2021 425

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 (Date of earliest event reported): July 26, 2021 (July 25, 2021) (Ex

? I ? 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 (Date of earliest event reported): July 26, 2021 (July 25, 2021) (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Comm

July 26, 2021 EX-99.2

Investor Presentation

Exhibit 99.2 ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

July 26, 2021 EX-99.1

Old Second and West Suburban Announce Combination to Create the Leading Community Bank in Chicago

? ? ? ? ? ? ? ? ? ? ? (NASDAQ:OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer July 26, 2021 ? (630) 906-5484 ? ? ? Old Second and West Suburban Announce Combination to Create the Leading Community Bank in Chicago ? AURORA and LOMBARD, Illinois July 26, 2021 (PRNewswire) - Old Second Bancorp, Inc. (Nasdaq: OSBC) (?Old Second?) and West Suburban Ban

July 21, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

? I ? 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 (Date of earliest event reported): July 21, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number)

July 21, 2021 EX-99.1

Old Second Reports Second Quarter Net Income of $8.8 million, or $0.30 per Diluted Share

? ? ? ? ? ? ? ? ? ? ? (NASDAQ:OSBC) Exhibit 99.1 ? ? ? Contact: Bradley S. Adams For Immediate Release ? Chief Financial Officer July 21, 2021 ? (630) 906-5484 ? ? ? ? Old Second Reports Second Quarter Net Income of $8.8 million, or $0.30 per Diluted Share ? AURORA, IL, July 21, 2021 ? Old Second Bancorp, Inc. (the ?Company,? ?we,? ?us,? and ?our?) (NASDAQ: OSBC), the parent company of Old Second

July 21, 2021 EX-99.2

99.2 Loan Portfolio Disclosures for Old Second Bancorp, Inc. dated June 30, 2021

July 20, 2021 8-K

Current Report

? I ? 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 (Date of earliest event reported): July 20, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number

July 8, 2021 8-K

Current Report

? I ? 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 (Date of earliest event reported): July 7, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number)

June 25, 2021 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 11-K ANNUAL REPORT Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the

I ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? Form 11-K ? ANNUAL REPORT ? Pursuant to Section 15 (d) of the Securities Exchange Act of 1934 ? xANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the fiscal year ended December 31, 2020 ? OR ? oTRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the

May 19, 2021 8-K

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

? I ? 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 (Date of earliest event reported): May 18, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (

May 18, 2021 EX-99.1

Old Second Bancorp, Inc. Annual Stockholders Meeting

EX-99.1 2 osbc-20210518ex991e078fd.htm EX-99.1 (NASDAQ:OSBC) Exhibit 99.1 Contact: James L. Eccher For Immediate Release President, Chief Executive Officer May 18, 2021 (630) 966-2435 Old Second Bancorp, Inc. Annual Stockholders Meeting AURORA, IL, – Old Second Bancorp, Inc. (“Old Second”) (NASDAQ: OSBC), announced: ●The Annual Stockholders Meeting will be held on May 18, 2021 at 9:00am CDT. Inves

May 18, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

? I ? 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 (Date of earliest event reported): May 18, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number) (

May 7, 2021 10-Q

Quarterly Report - 10-Q

Table of Contents I ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

April 21, 2021 EX-99.1

Old Second Reports First Quarter Net Income of $11.9 million, or $0.40 per Diluted Share, Increases Quarterly Dividend to $0.05 per Share

EX-99.1 2 osbc-20210421ex9912ac345.htm EX-99.1 (NASDAQ:OSBC) Exhibit 99.1 Contact: Bradley S. Adams For Immediate Release Chief Financial Officer April 21, 2021 (630) 906-5484 Old Second Reports First Quarter Net Income of $11.9 million, or $0.40 per Diluted Share, Increases Quarterly Dividend to $0.05 per Share AURORA, IL, April 21, 2021 – Old Second Bancorp, Inc. (the “Company,” “we,” “us,” and

April 21, 2021 EX-99.2

99.2 Loan Portfolio Disclosures for Old Second Bancorp, Inc. dated March 31, 2021

April 21, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

? I ? 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 (Date of earliest event reported): April 21, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number)

April 20, 2021 8-K

Current Report

? I ? 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 (Date of earliest event reported): April 20, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numbe

April 16, 2021 DEF 14A

Definitive Proxy Statement on 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)) ?

April 8, 2021 EX-10.1

Form of Subordinated Note Purchase Agreement, dated as of April 6, 2021, by and among Old Second Bancorp, Inc. and the Purchasers

Exhibit 10.1 FORM OF SUBORDINATED NOTE PURCHASE AGREEMENT This SUBORDINATED NOTE PURCHASE AGREEMENT (this ?Agreement?) is dated as of April 6, 2021, and is made by and among OLD SECOND BANCORP, INC., a Delaware corporation (the ?Company?), and the purchasers of the Subordinated Notes (as defined herein) identified on the signature pages hereto (each a ?Purchaser? and collectively, the ?Purchasers?

April 8, 2021 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

? I ? 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 (Date of earliest event reported): April 6, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Numb

April 8, 2021 EX-4.1

Form of 3.50% Fixed-to-Floating Subordinated Note due April 15, 2031 of Old Second Bancorp, Inc. (incorporated by reference to Exhibit 4.1 of the Company’s Current Report on Form 8-K filed on April 7, 2021).

Exhibit 4.1 SUBORDINATED NOTE ? OLD SECOND BANCORP, INC. 3.50% FIXED-TO-FLOATING RATE Subordinated Note due april 15, 2031 THE INDEBTEDNESS EVIDENCED BY THIS SUBORDINATED NOTE IS SUBORDINATED AND JUNIOR IN RIGHT OF PAYMENT TO SENIOR INDEBTEDNESS (AS DEFINED IN SECTION 3 OF THIS SUBORDINATED NOTE) OF OLD SECOND BANCORP, INC. (THE ?COMPANY?), INCLUDING OBLIGATIONS OF THE COMPANY TO ITS GENERAL CREDI

April 8, 2021 EX-99.1

Old Second Bancorp, Inc. Subordinated Note Placement Investor Presentation dated March 2021

Exhibit 99.1 ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

April 1, 2021 8-K

Current Report

? I ? 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 (Date of earliest event reported): April 1, 2021 (Exact name of registrant as specified in its charter) ? ? ? Delaware 000-10537 36-3143493 (State or other jurisdiction of incorporation) (Commission File Number

March 19, 2021 EX-10.1

Compensation and Benefits Assurance Agreement dated as of March 16, 2021, between Old Second Bancorp, Inc. and Richard A. Gartelmann, Jr., Executive Vice President.

? ? ? COMPENSATION AND BENEFITS ASSURANCE AGREEMENT ? ? ? Richard A. Gartelmann, Jr. March 2021 ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? 2673058.DOC1 ? COMPENSATION AND BENEFITS ASSURANCE AGREEMENT This COMPENSATION AND BENEFITS ASSURANCE AGREEMENT (this ?Agreement?) is made, entered into, and is effective as of this 16th day of March, 2021 (the ?Effective Date?) by and between OLD SECOND BANCORP, INC. (

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