| League Two | 08/10/22 | Stenhousemuir FC | - | Annan Athletic | 2:2 |  |
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| League Two | 18/02/23 | Annan Athletic | - | Stirling Albion FC | 2:2 | ||||
| League Cup | 16/07/24 | Annan Athletic | - | Bonnyrigg Rose Athletic | 7:6 pso | ||||
| League One | 03/08/24 | Cove Rangers | - | Annan Athletic | 1:3 |
England