| Date | Name | Title | Type | Security | Shares | Price | Value | Ownership | Reported |
| 08/08/2023 | Lyons Billy J Jr. | Director | Grant | Old Second Bancorp, Inc. Common Stock | 21 | $15.99 | $335.8 | | 08/08/2023 |
| 06/30/2023 | Eccher James | CHAIRMAN AND CEO | Grant | Old Second Bancorp, Inc. Common Stock | 140 | $0.00 | $0 | By 401-K | 06/30/2023 |
| 06/30/2023 | Eccher James | CHAIRMAN AND CEO | Grant | Old Second Bancorp, Inc. Common Stock | 27 | $0.00 | $0 | By Profit Sharing | 06/30/2023 |
| 06/30/2023 | COLLINS GARY S | VICE CHAIRMAN | Grant | Old Second Bancorp, Inc. Common Stock | 26 | $0.00 | $0 | By 401-K | 06/30/2023 |
| 06/30/2023 | Pilmer Donald | EVP | Grant | Old Second Bancorp, Inc. Common Stock | 17 | $0.00 | $0 | By 401-K Plan | 06/30/2023 |
| 06/30/2023 | ADAMS BRADLEY S. | CFO | Grant | Old Second Bancorp, Inc. Common Stock | 43 | $0.00 | $0 | By 401-k Plan | 06/30/2023 |
| 06/30/2023 | Gartelmann Richard A JR | EVP | Grant | Old Second Bancorp, Inc. Common Stock | 140 | $0.00 | $0 | By 401-K | 06/30/2023 |
| 05/09/2023 | Lyons Billy J Jr. | Director | Grant | Old Second Bancorp, Inc. Common Stock | 30 | $11.15 | $334.5 | | 05/09/2023 |
| 03/31/2023 | ADAMS BRADLEY S. | CFO | Other (acquisition) | Old Second Bancorp, Inc. Common Stock | 28 | $0.00 | $0 | By 401-k Plan | 03/31/2023 |
| 03/31/2023 | Eccher James | CHAIRMAN AND CEO | Other (acquisition) | Old Second Bancorp, Inc. Common Stock | 18 | $0.00 | $0 | By Profit Sharing | 03/31/2023 |
| 03/31/2023 | Eccher James | CHAIRMAN AND CEO | Other (acquisition) | Old Second Bancorp, Inc. Common Stock | 372 | $0.00 | $0 | By 401-K | 03/31/2023 |
| 03/31/2023 | COLLINS GARY S | VICE CHAIRMAN | Other (acquisition) | Old Second Bancorp, Inc. Common Stock | 77 | $0.00 | $0 | By 401-K | 03/31/2023 |
| 03/31/2023 | Pilmer Donald | EVP | Other (acquisition) | Old Second Bancorp, Inc. Common Stock | 1 | $0.00 | $0 | By Profit Sharing Plan | 03/31/2023 |
| 03/31/2023 | Pilmer Donald | EVP | Other (acquisition) | Old Second Bancorp, Inc. Common Stock | 11 | $0.00 | $0 | By 401-K Plan | 03/31/2023 |
| 03/31/2023 | Gartelmann Richard A JR | EVP | Other (acquisition) | Old Second Bancorp, Inc. Common Stock | 156 | $0.00 | $0 | By 401-K | 03/31/2023 |
| 03/23/2023 | Kotche Keith | Director | Grant | Old Second Bancorp, Inc. Common Stock | 5.5k | $13.75 | $75k | | 03/23/2023 |
| 03/13/2023 | Kotche Keith | Director | Grant | Old Second Bancorp, Inc. Common Stock | 5.3k | $14.33 | $75.5k | | 03/10/2023 |
| 03/10/2023 | Kotche Keith | Director | Grant | Old Second Bancorp, Inc. Common Stock | 4.8k | $15.00 | $72.7k | | 03/10/2023 |
| 03/01/2023 | Gartelmann Richard A JR | EVP | Grant | Old Second Bancorp, Inc. Common Stock | 5.2k | $0.00 | $0 | | 02/21/2023 |
| 03/01/2023 | Pilmer Donald | EVP | Grant | Old Second Bancorp, Inc. Common Stock | 10.5k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | Williams John JR | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | Finn Barry | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | Temple Rocks Patti | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | Tapscott James F | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | SKOGLUND WILLIAM B | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | Pilmer Donald | EVP | Grant | Old Second Bancorp, Inc. Common Stock | 16.5k | $0.00 | $0 | | 02/18/2023 |
| 02/21/2023 | MCLEAN HUGH H | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | Lyons Billy J Jr. | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/07/2023 |
| 02/21/2023 | Ladowicz John | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | Kotche Keith | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | KLAESER DENNIS L | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | KANE WILLIAM | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/21/2023 | Gartelmann Richard A JR | EVP | Grant | Old Second Bancorp, Inc. Common Stock | 16.5k | $0.00 | $0 | | 02/18/2023 |
| 02/21/2023 | Eccher James | CHAIRMAN AND CEO | Grant | Old Second Bancorp, Inc. Common Stock | 50.1k | $0.00 | $0 | | 02/18/2023 |
| 02/21/2023 | YORK JILL E | Director | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
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