| 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 |
Scotland
USA