| FA Cup | 29.11.14 | Annan Athletic | - | Brechin City FC | 1:1 | ||||
| FA Cup | 09.12.14 | Brechin City FC | - | Annan Athletic | 4:2 | ||||
| League Two | 17.09.22 | Annan Athletic | - | East Fife FC | 2:2 | ||||
| League Two | 03.12.22 | East Fife FC | - | Annan Athletic | 1:3 |  |
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| League Two | 28.01.23 | Annan Athletic | - | East Fife FC | 3:0 | ||||
| League Two | 01.04.23 | East Fife FC | - | Annan Athletic | 0:1 | ||||
| Playoffs | 13.05.25 | East Fife FC | - | Annan Athletic | 3:2 |  |
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| Playoffs | 16.05.25 | Annan Athletic | - | East Fife FC | 1:1 |
Schottland