| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 02/21/2023 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/21/2023 |
| 02/15/2022 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 3.1k | $0.00 | $0 | | 02/15/2022 |
| 03/08/2021 | OLD SECOND BANCORP INC | OSBC | Payment of Exercise | Old Second Bancorp, Inc. Common Stock | 1.6k | $13.78 | $21.8k | | 03/08/2021 |
| 02/16/2021 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 3.8k | $0.00 | $0 | | 02/16/2021 |
| 02/18/2020 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 1.5k | $0.00 | $0 | | 02/18/2020 |
| 06/03/2019 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 1.5k | $0.00 | $0 | | 06/03/2019 |
| 01/04/2019 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 1.5k | $7.49 | $11.2k | | 01/04/2019 |
| 04/17/2018 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 5k | $0.00 | $0 | | 04/17/2018 |
| 02/20/2018 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 1.5k | $0.00 | $0 | | 02/20/2018 |
| 06/17/2014 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 2.5k | $4.82 | $12k | | 06/17/2014 |
| 04/08/2014 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 11.4k | $4.40 | $50k | | 04/08/2014 |
| 01/19/2010 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp Inc. Common Stock | 1.2k | $0.00 | $0 | | 01/19/2010 |