| League Two | 25.09.21 | Annan Athletic | - | Edinburgh City FC | 1:3 | ||||
| League Two | 03.12.21 | Edinburgh City FC | - | Annan Athletic | 0:1 | ||||
| League Two | 09.04.22 | Annan Athletic | - | Cowdenbeath FC | 2:3 | ||||
| League Two | 17.09.22 | Annan Athletic | - | East Fife FC | 2:2 |  |
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| 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 | ||||
| League One | 19.08.23 | Queen Of The South | - | Annan Athletic | 3:1 | ||||
| League One | 21.10.23 | Annan Athletic | - | Queen Of The South | 0:1 | |
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| League One | 30.12.23 | Queen Of The South | - | Annan Athletic | 2:1 | ||||
| League One | 09.03.24 | Annan Athletic | - | Queen Of The South | 2:1 |
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