| League Two | 28.08.21 | Cowdenbeath FC | - | Annan Athletic | 1:3 |  |
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| League Two | 30.10.21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
| League Two | 08.01.22 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
| League Two | 09.04.22 | Annan Athletic | - | Cowdenbeath FC | 2:3 | ||||
| League One | 23.09.23 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
| League One | 03.02.24 | Annan Athletic | - | Alloa Athletic | 2:3 | ||||
| League One | 30.03.24 | Alloa Athletic | - | Annan Athletic | 1:1 | |
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| League One | 21.09.24 | Arbroath FC | - | Annan Athletic | 2:0 | ||||
| League One | 21.12.24 | Annan Athletic | - | Arbroath FC | 0:4 | |
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| League One | 15.02.25 | Cove Rangers | - | Annan Athletic | 3:1 | ||||
| League One | 03.05.25 | Annan Athletic | - | Cove Rangers | 2:4 |
Schotland