| League Cup | 25.07.17 | Dumbarton FC | - | Annan Athletic | 3:4 i.E. | ||||
| League Cup | 10.07.21 | Airdrieonians FC | - | Annan Athletic | 4:5 i.E. | ||||
| League Cup | 20.07.24 | Arbroath FC | - | Annan Athletic | 0:3 | ||||
| League One | 21.09.24 | Arbroath FC | - | Annan Athletic | 2:0 | ||||
| League One | 21.12.24 | Annan Athletic | - | Arbroath FC | 0:4 | ||||
| League One | 01.03.25 | Arbroath FC | - | Annan Athletic | 3:0 |  |
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| League One | 19.04.25 | Annan Athletic | - | Arbroath FC | 5:1 |
Schottland