| 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 |
Scotland