| League Two | 30.07.22 | Stranraer FC | - | Annan Athletic | 1:0 | ||||
| League Two | 05.11.22 | Forfar Athletic | - | Annan Athletic | 1:4 | ||||
| League Two | 11.03.23 | Annan Athletic | - | Elgin City | 4:1 | ||||
| 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 |
Écosse