| League Two | 23.12.22 | Annan Athletic | - | Albion Rovers | 5:1 | ||||
| League Two | 25.02.23 | Albion Rovers | - | Annan Athletic | 0:2 | ||||
| League Two | 15.04.23 | Annan Athletic | - | Albion Rovers | 4:0 |  |
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| League One | 11.11.23 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| League One | 06.01.24 | Annan Athletic | - | Montrose FC | 2:2 |  |
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| League One | 16.03.24 | Montrose FC | - | Annan Athletic | 1:1 | |
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| League Cup | 23.07.24 | Dundee FC | - | Annan Athletic | 3:1 |
Schotland