[1] Dumbarton 2-1 Annan Athletic [3] 2023-02-11 15:00
Stadium: YOUR Radio 103FM Stadium Pitch: Regular Round: 24
Head to Head
| Scotland League Two | 2022/10/29 14:00 | Annan Athletic v Dumbarton | W | 0-1 |
| Scotland League Two | 2022/08/13 14:00 | Dumbarton v Annan Athletic | W | 4-0 |
| Scotland League Cup | 2019/07/13 14:00 | Annan Athletic v Dumbarton | W | 0-1 |
| Scotland League Cup | 2017/07/25 18:45 | Dumbarton v Annan Athletic | L | 3-4 |