Head to Head
| Scotland League One Play-Offs | 2023/05/13 14:00 | Dumbarton v Annan Athletic | D | 0-0 |
| Scotland League One Play-Offs | 2023/05/09 18:45 | Annan Athletic v Dumbarton | W | 6-0 |
| Scotland League Two | 2023/04/08 14:00 | Annan Athletic v Dumbarton | W | 3-1 |
| Scotland League Two | 2023/02/11 15:00 | Dumbarton v Annan Athletic | L | 2-1 |
| Scotland League Two | 2022/10/29 14:00 | Annan Athletic v Dumbarton | L | 0-1 |
| Scotland League Two | 2022/08/13 14:00 | Dumbarton v Annan Athletic | L | 4-0 |
| Scotland League Cup | 2019/07/13 14:00 | Annan Athletic v Dumbarton | L | 0-1 |
| Scotland League Cup | 2017/07/25 18:45 | Dumbarton v Annan Athletic | W | 3-4 |