| League Cup | 10.07.21 | Airdrieonians FC | - | Annan Athletic | 4:5 pn. | ||||
| League Two | 15.01.22 | Annan Athletic | - | Forfar Athletic | 2:2 |  |
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| League Two | 26.03.22 | Annan Athletic | - | Albion Rovers | 2:4 | ||||
| Playoffs | 07.05.22 | Forfar Athletic | - | Annan Athletic | 1:1 | ||||
| League One | 28.10.23 | Edinburgh City | - | Annan Athletic | 3:2 | |
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| League One | 23.12.23 | Annan Athletic | - | Falkirk FC | 0:3 | |
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| League One | 10.02.24 | Hamilton Academical | - | Annan Athletic | 2:3 | |
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| League One | 02.03.24 | Falkirk FC | - | Annan Athletic | 1:1 | ||||
| League One | 01.03.25 | Arbroath FC | - | Annan Athletic | 3:0 |
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