| League Two | 31.07.21 | Annan Athletic | - | Forfar Athletic | 0:2 |  |
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| League Two | 16.04.22 | Forfar Athletic | - | Annan Athletic | 5:1 | ||||
| Playoffs | 03.05.22 | Annan Athletic | - | Forfar Athletic | 1:0 | ||||
| Playoffs | 07.05.22 | Forfar Athletic | - | Annan Athletic | 1:1 | ||||
| League Cup | 18.07.23 | Dunfermline Athletic | - | Annan Athletic | 4:0 |  |
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| League One | 08.03.25 | Annan Athletic | - | Stenhousemuir FC | 0:2 |
Schottland