| League Cup | 09.07.22 | Queen Of The South | - | Annan Athletic | 2:3 |  |
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| 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 | ||||
| League One | 17.08.24 | Queen Of The South | - | Annan Athletic | 2:0 |  |
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| League One | 01.03.25 | Arbroath FC | - | Annan Athletic | 3:0 | ||||
| League One | 19.04.25 | Annan Athletic | - | Arbroath FC | 5:1 |
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