| 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 |
| 09/03/2021 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 6.8k | $11.81 | $80.7k | | 09/01/2021 |
| 09/02/2021 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 203 | $11.85 | $2.4k | | 09/01/2021 |
| 09/01/2021 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 3k | $11.72 | $34.7k | | 09/01/2021 |
| 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 |
| 08/06/2019 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 5k | $11.97 | $59.8k | | 08/06/2019 |
| 06/03/2019 | OLD SECOND BANCORP INC | OSBC | Grant | Old Second Bancorp, Inc. Common Stock | 1.5k | $0.00 | $0 | | 06/03/2019 |
| 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 |
| 02/21/2017 | OLD SECOND BANCORP INC | OSBC | Grant | Old second Bancorp, Inc. Common Stock | 2.5k | $0.00 | $0 | | 02/21/2017 |