| League Cup | 16.07.19 | Queen Of The South | - | Annan Athletic | 5:4 pn. |  |
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| 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 One | 28.10.23 | Edinburgh City | - | Annan Athletic | 3:2 |  |
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| League Cup | 16.07.24 | Annan Athletic | - | Bonnyrigg Rose Athletic | 7:6 pn. | ||||
| League One | 28.09.24 | Kelty Hearts | - | Annan Athletic | 3:0 | |
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| League One | 16.11.24 | Annan Athletic | - | Kelty Hearts | 0:2 |
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