| 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 | 27/01/24 | Annan Athletic | - | Edinburgh City | 3:0 | ||||
| League One | 20/04/24 | Edinburgh City | - | Annan Athletic | 1:2 | |
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| Playoffs | 06/05/25 | Elgin City | - | Annan Athletic | 2:4 | ||||
| Playoffs | 10/05/25 | Annan Athletic | - | Elgin City | 1:2 | |
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Scotland