| League Cup | 25/07/17 | Dumbarton FC | - | Annan Athletic | 3:4 pso | ||||
| League Cup | 13/07/19 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| League Two | 13/08/22 | Dumbarton FC | - | Annan Athletic | 4:0 |  |
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| League Two | 08/04/23 | Annan Athletic | - | Dumbarton FC | 3:1 | ||||
| Playoffs | 09/05/23 | Annan Athletic | - | Dumbarton FC | 6:0 |
England