| 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 | |
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| 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 | ||||
| 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 |
England