| League Two | 02.10.21 | Kelty Hearts | - | Annan Athletic | 2:1 | ||||
| League Two | 26.12.21 | Annan Athletic | - | Kelty Hearts | 5:1 |  |
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| League Two | 26.02.22 | Kelty Hearts | - | Annan Athletic | 3:1 |  |
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| 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 |
England