| League Two | 14.08.21 | Annan Athletic | - | Stirling Albion FC | 3:1 |  |
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| League Two | 18.12.21 | Stirling Albion FC | - | Annan Athletic | 2:3 | ||||
| League Two | 29.01.22 | Annan Athletic | - | Stirling Albion FC | 0:0 | ||||
| League Two | 19.03.22 | Stirling Albion FC | - | Annan Athletic | 0:3 | ||||
| Playoffs | 16.05.23 | Annan Athletic | - | Clyde FC | 3:1 | ||||
| Playoffs | 19.05.23 | Clyde FC | - | Annan Athletic | 1:2 |  |
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| League One | 23.09.23 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
| League One | 03.02.24 | Annan Athletic | - | Alloa Athletic | 2:3 | |
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| League One | 13.02.24 | Alloa Athletic | - | Annan Athletic | 2:1 | ||||
| League One | 30.03.24 | Alloa Athletic | - | Annan Athletic | 1:1 | |
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| League One | 24.08.24 | Annan Athletic | - | Alloa Athletic | 0:1 | ||||
| League One | 22.02.25 | Annan Athletic | - | Alloa Athletic | 3:4 | ||||
| League One | 12.04.25 | Alloa Athletic | - | Annan Athletic | 1:0 |
Schotland
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