| 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 |
| 04/27/2020 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 1.1k | $6.97 | $7.7k | IRA | 04/27/2020 |
| 04/27/2020 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bncorp, Inc. Common Stock | 601 | $6.95 | $4.2k | IRA | 04/27/2020 |
| 04/27/2020 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 300 | $6.96 | $2.1k | IRA | 04/27/2020 |
| 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 | Other (acquisition) | Old Second Bancorp, Inc. Common Stock | 2.5k | $0.00 | $0 | IRA | 06/03/2019 |
| 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 |
| 08/28/2017 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 550 | $11.48 | $6.3k | IRA | 08/28/2017 |
| 08/29/2016 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 4k | $8.11 | $32.1k | IRA | 08/29/2016 |
| 08/29/2016 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 600 | $8.11 | $4.9k | IRA | 08/29/2016 |
| 08/29/2016 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 100 | $8.10 | $810.2 | IRA | 08/29/2016 |
| 08/29/2016 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 500 | $8.09 | $4k | IRA | 08/29/2016 |
| 08/29/2016 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 200 | $8.09 | $1.6k | IRA | 08/29/2016 |
| 08/29/2016 | OLD SECOND BANCORP INC | OSBC | Purchase | Old Second Bancorp, Inc. Common Stock | 643 | $8.08 | $5.2k | IRA | 08/29/2016 |