| League One | 30.12.23 | Queen Of The South | - | Annan Athletic | 2:1 |  |
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| League One | 23.03.24 | Annan Athletic | - | Kelty Hearts | 3:2 | |
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| League One | 19.10.24 | Inverness CT | - | Annan Athletic | 1:0 | ||||
| League One | 08.02.25 | Annan Athletic | - | Dumbarton FC | 2:1 | ||||
| League One | 29.03.25 | Annan Athletic | - | Kelty Hearts | 2:1 |
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