| League Two | 17.09.22 | Annan Athletic | - | East Fife FC | 2:2 | ||||
| League Two | 03.12.22 | East Fife FC | - | Annan Athletic | 1:3 | ||||
| League Two | 28.01.23 | Annan Athletic | - | East Fife FC | 3:0 | ||||
| League Two | 01.04.23 | East Fife FC | - | Annan Athletic | 0:1 |  |
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| League Cup | 20.07.24 | Arbroath FC | - | Annan Athletic | 0:3 | ||||
| League One | 09.11.24 | Annan Athletic | - | Stenhousemuir FC | 1:1 | ||||
| League One | 04.01.25 | Stenhousemuir FC | - | Annan Athletic | 1:1 | ||||
| League One | 19.04.25 | Annan Athletic | - | Arbroath FC | 5:1 | |
Écosse