| League Two | 27.08.22 | Albion Rovers | - | Annan Athletic | 2:2 | ||||
| League One | 11.11.23 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| League One | 16.12.23 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| League One | 14.12.24 | Dumbarton FC | - | Annan Athletic | 1:5 |  |
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| League One | 15.02.25 | Cove Rangers | - | Annan Athletic | 3:1 |
Inglaterra