| League Two | 05/02/22 | Annan Athletic | - | Stenhousemuir FC | 0:2 | ||||
| League Two | 26/02/22 | Kelty Hearts | - | Annan Athletic | 3:1 |  |
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| League One | 16/09/23 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| League One | 04/11/23 | Annan Athletic | - | Kelty Hearts | 2:2 | |
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| League One | 09/12/23 | Annan Athletic | - | Cove Rangers | 1:3 | ||||
| League One | 20/04/24 | Edinburgh City | - | Annan Athletic | 1:2 |  |
England