| League Two | 18.02.23 | Annan Athletic | - | Stirling Albion FC | 2:2 |  |
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| League Two | 08.04.23 | Annan Athletic | - | Dumbarton FC | 3:1 |  |
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| League One | 06.01.24 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| League Cup | 16.07.24 | Annan Athletic | - | Bonnyrigg Rose Athletic | 7:6 tab | ||||
| League One | 03.08.24 | Cove Rangers | - | Annan Athletic | 1:3 | ||||
| Chall. Cup | 07.09.24 | Stranraer FC | - | Annan Athletic | 1:5 | |
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| League One | 26.10.24 | Annan Athletic | - | Queen Of The South | 1:0 | |
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| League One | 07.12.24 | Annan Athletic | - | Cove Rangers | 1:1 |
Écosse