| League Cup | 20.07.21 | Annan Athletic | - | Queen's Park FC | 1:2 | ||||
| League One | 10.02.24 | Hamilton Academical | - | Annan Athletic | 2:3 |  |
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| League One | 06.04.24 | Annan Athletic | - | Hamilton Academical | 1:3 | ||||
| League Cup | 13.07.24 | Annan Athletic | - | Inverness CT | 1:0 | ||||
| League One | 10.08.24 | Annan Athletic | - | Inverness CT | 1:0 | ||||
| League One | 19.10.24 | Inverness CT | - | Annan Athletic | 1:0 |
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