OLD SECOND BANCORP INC | Business Contracts

Description of Capital Stock (Filed With SEC on March 9, 2023)

Description of Capital Stock (Filed With SEC on March 10, 2022)

EXECUTIVE EMPLOYMENT AGREEMENT (Filed With SEC on December 1, 2021)

Form of 3.50% Fixed-to-Floating Subordinated Note due April 15, 2031 of Old Second Bancorp, Inc (Filed With SEC on April 8, 2021)

Form of Subordinated Note Purchase Agreement, dated as of April 6, 2021, by and among Old Second Bancorp, Inc. and the Purchasers (Filed With SEC on April 8, 2021)

Compensation and Benefits Assurance Agreement dated as of March 16, 2021, between Old Second Bancorp, Inc. and Richard A. Gartelmann, Jr., Executive Vice President (Filed With SEC on March 19, 2021)

Description of Capital Stock (Filed With SEC on March 8, 2021)

Compensation and Benefits Assurance Agreement, effective June 17, 2014, between the Company and Richard A. Gartelmann (Filed With SEC on March 8, 2021)

Form of Performance-Based Restricted Stock Unit Agreement (Filed With SEC on February 18, 2021)

Description of Capital Stock (Filed With SEC on March 6, 2020)

Old Second Bancorp, Inc. Amended and Restated Voluntary Deferred Compensation Plan for Directors dated September 1, 2008 (Filed With SEC on March 6, 2020)

Old Second Bancorp, Inc. Amended and Restated Voluntary Deferred Compensation Plan for Executives dated September 1, 2008 (Filed With SEC on March 6, 2020)

Restated Old Second Bancorp, Inc. 2014 Equity Incentive Plan (restated to combine the 2014 Equity Incentive Plan included (Filed With SEC on November 7, 2018)

Form of Director Performance-Based Restricted Stock Agreement (Filed With SEC on August 7, 2018)

Form of Performance-Based Restricted Stock Unit Agreement (Filed With SEC on April 18, 2018)

Executive Annual Incentive Plan dated February 19, 2018 (Filed With SEC on February 23, 2018)

Sample Compensation and Benefits Assurance Agreement dated as of September 1, 2017, between Old Second Bancorp, Inc. and the Executive Vice President as named in the agreement (Filed With SEC on September 1, 2017)

First Amendment of Old Second Bancorp, Inc. Employment Agreement with James Eccher dated as of September 1, 2017 (Filed With SEC on September 1, 2017)

COMPENSATION AND BENEFITS ASSURANCE AGREEMENT GARY COLLINS (Filed With SEC on April 28, 2017)

COMPENSATION AND BENEFITS ASSURANCE AGREEMENT (Filed With SEC on April 25, 2017)

RETIREMENT AGREEMENT AND RELEASE (Filed With SEC on March 17, 2017)

OLD SECOND BANCORP, INC., as Issuer and WELLS FARGO BANK, NATIONAL ASSOCIATION, as Trustee INDENTURE Dated as of December 15, 2016 (Filed With SEC on December 15, 2016)

OLD SECOND BANCORP, INC., Company and WELLS FARGO BANK, NATIONAL ASSOCIATION, Trustee FIRST SUPPLEMENTAL INDENTURE DATED AS OF DECEMBER 15, 2016 TO INDENTURE DATED AS OF DECEMBER... (Filed With SEC on December 15, 2016)

$45,000,000 OLD SECOND BANCORP, INC. 5.750% Fixed-to-Floating Rate Senior Notes due 2026 UNDERWRITING AGREEMENT (Filed With SEC on December 15, 2016)

COMPENSATION AND BENEFITS ASSURANCE AGREEMENT (Filed With SEC on November 8, 2016)

SECOND AMENDMENT TO AMENDED AND RESTATED RIGHTS AGREEMENT AND TAX BENEFITS PRESERVATION PLAN (Filed With SEC on September 4, 2015)

OLD SECOND BANCORP, INC. EMPLOYMENT AGREEMENT (Filed With SEC on September 18, 2014)

FIRST AMENDMENT TO AMENDED AND RESTATED RIGHTS AGREEMENT AND TAX BENEFITS PRESERVATION PLAN (Filed With SEC on August 13, 2014)

OLD SECOND BANCORP, INC. (a Delaware corporation) [ ] Shares of Common Stock (Par Value $1.00 Per Share) UNDERWRITING AGREEMENT (Filed With SEC on March 26, 2014)

INCORPORATED UNDER THE LAWS OF THE STATE OF DELAWARE OLD SECOND BANCORP, INC. AURORA, ILLINOIS (Filed With SEC on January 17, 2014)

OLD SECOND BANCORP, INC. and OLD SECOND NATIONAL BANK, as Rights Agent AMENDED AND RESTATED RIGHTS AGREEMENT AND TAX BENEFITS PRESERVATION PLAN Dated as of September 12, 2012 (Filed With SEC on September 13, 2012)

UNITED STATES OF AMERICA BEFORE THE BOARD OF GOVERNORS OF THE FEDERAL RESERVE SYSTEM WASHINGTON, D.C. (Filed With SEC on August 9, 2011)

OLDSECOND BANCORP, INC. 2008EQUITY INCENTIVE PLAN NON-QUALIFIEDSTOCK OPTION (Filed With SEC on February 23, 2009)

OLD SECOND BANCORP, INC. 2008 EQUITY INCENTIVE PLAN INCENTIVE STOCK OPTION (Filed With SEC on February 23, 2009)

OLD SECOND BANCORP, INC. 2008 EQUITY INCENTIVE PLAN RESTRICTED STOCK AWARD AGREEMENT (Filed With SEC on February 23, 2009)

OLD SECOND BANCORP, INC. 2008 EQUITY INCENTIVE PLAN RESTRICTEDSTOCK UNIT AWARD AGREEMENT (Filed With SEC on February 23, 2009)

Incorporated Under the Laws of the State of Delaware (Filed With SEC on January 16, 2009)

WARRANTTO PURCHASE COMMON STOCK (Filed With SEC on January 16, 2009)

UNITED STATES DEPARTMENT OF THE TREASURY 1500 PENNSYLVANIA AVENUE, NW WASHINGTON, D.C. 20220 (Filed With SEC on January 16, 2009)

WAIVER (Filed With SEC on January 16, 2009)

[OLD SECOND BANCORP LETTERHEAD] January , 2009 (Filed With SEC on January 16, 2009)

LOAN AND SUBORDINATED DEBENTURE PURCHASE AGREEMENT between LASALLE BANK NATIONAL ASSOCIATION and OLD SECOND BANCORP, INC. Dated as of January 31, 2008 (Filed With SEC on March 17, 2008)

AGREED UPON TERMS AND PROCEDURES (Filed With SEC on March 17, 2008)

AGREEMENT AND PLAN OF MERGER AMONG OLD SECOND BANCORP, INC., OLD SECOND ACQUISITION, INC. AND HERITAGEBANC, INC. NOVEMBER 5, 2007 (Filed With SEC on November 6, 2007)

PROMISSORY NOTE (Filed With SEC on May 9, 2007)

PROMISSORY NOTE (Filed With SEC on March 15, 2007)

SUMMARY OF FEES FOR BOARD OF DIRECTORS (Filed With SEC on March 15, 2007)

COMPENSATIONAND BENEFITS ASSURANCEAGREEMENT [EXECUTIVE] (Filed With SEC on November 8, 2006)

SUMMARY OF FEES FOR BOARD OFDIRECTORS (Filed With SEC on March 14, 2006)

OLD SECOND BANCORP, INC. 2002 LONG-TERM INCENTIVE PLAN AMENDEDSTOCK OPTION AWARD AGREEMENT (Filed With SEC on December 21, 2005)

AMENDMENT2005-1 TO THE OLD SECOND BANCORP, INC. SUPPLEMENTALEXECUTIVE RETIREMENT PLAN (Filed With SEC on October 24, 2005)

SUMMARY OF FEES FOR BOARD OF DIRECTORS (Filed With SEC on March 15, 2005)

COMPENSATION AND BENEFITS ASSURANCE AGREEMENT FOR Old Second Bancorp, Inc. (Amended 3/1/2000) James Eccher (Filed With SEC on February 10, 2005)

OLD SECOND BANCORP INC (53)