| League Two | 28.08.21 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
| League Two | 19.02.22 | Annan Athletic | - | Edinburgh City FC | 2:1 | ||||
| League Two | 30.04.22 | Annan Athletic | - | Kelty Hearts | 1:2 | ||||
| League Two | 13.08.22 | Dumbarton FC | - | Annan Athletic | 4:0 | ||||
| League Two | 17.09.22 | Annan Athletic | - | East Fife FC | 2:2 |  |
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| League Two | 08.04.23 | Stenhousemuir FC | - | Bonnyrigg Rose Athletic | 0:0 |
Écosse