| League One | 26/08/23 | Annan Athletic | - | Edinburgh City | 3:2 |  |
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| League One | 28/10/23 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| League One | 17/02/24 | Annan Athletic | - | Stirling Albion FC | 2:1 | |
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| League One | 04/05/24 | Stirling Albion FC | - | Annan Athletic | 1:1 |
Scotland