| League Cup | 10.11.20 | Albion Rovers | - | Annan Athletic | 1:5 | ||||
| League Two | 21.08.21 | Albion Rovers | - | Annan Athletic | 0:1 |  |
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| League Two | 20.11.21 | Annan Athletic | - | Albion Rovers | 1:1 | ||||
| League Two | 02.03.22 | Albion Rovers | - | Annan Athletic | 1:4 | ||||
| League One | 19.08.23 | Queen Of The South | - | Annan Athletic | 3:1 | ||||
| League One | 21.10.23 | Annan Athletic | - | Queen Of The South | 0:1 | |
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| League One | 30.12.23 | Queen Of The South | - | Annan Athletic | 2:1 | |
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| League One | 09.03.24 | Annan Athletic | - | Queen Of The South | 2:1 | ||||
| League One | 17.08.24 | Queen Of The South | - | Annan Athletic | 2:0 | ||||
| League One | 26.10.24 | Annan Athletic | - | Queen Of The South | 1:0 | ||||
| League One | 28.12.24 | Queen Of The South | - | Annan Athletic | 1:1 |
Écosse