| League Cup | 15.07.17 | Clyde FC | - | Annan Athletic | 2:1 |  |
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| Playoffs | 14.05.19 | Annan Athletic | - | Clyde FC | 1:0 | ||||
| Playoffs | 18.05.19 | Clyde FC | - | Annan Athletic | 2:0 |  |
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| League Two | 14.08.21 | Annan Athletic | - | Stirling Albion FC | 3:1 | ||||
| League Two | 19.03.22 | Stirling Albion FC | - | Annan Athletic | 0:3 | ||||
| League Two | 13.08.22 | Dumbarton FC | - | Annan Athletic | 4:0 | ||||
| League Two | 29.10.22 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| League Two | 11.02.23 | Dumbarton FC | - | Annan Athletic | 2:1 | ||||
| League Two | 08.04.23 | Annan Athletic | - | Dumbarton FC | 3:1 | ||||
| Playoffs | 09.05.23 | Annan Athletic | - | Dumbarton FC | 6:0 | ||||
| Playoffs | 13.05.23 | Dumbarton FC | - | Annan Athletic | 0:0 |
Schotland