| 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 |
Scotland