| League Two | 18.03.23 | Forfar Athletic | - | Annan Athletic | 2:1 | ||||
| League One | 13.02.24 | Alloa Athletic | - | Annan Athletic | 2:1 |  |
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| League One | 06.04.24 | Annan Athletic | - | Hamilton Academical | 1:3 | |
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| League One | 23.11.24 | Montrose FC | - | Annan Athletic | 2:1 | |
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| League One | 22.03.25 | Montrose FC | - | Annan Athletic | 3:1 |
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