| League Cup | 13/10/20 | Ayr United | - | Annan Athletic | 1:0 | ||||
| League Cup | 19/07/22 | Annan Athletic | - | Ayr United | 5:4 pso | ||||
| League One | 29/09/23 | Hamilton Academical | - | Annan Athletic | 5:0 | ||||
| League One | 28/11/23 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| League One | 06/04/24 | Annan Athletic | - | Hamilton Academical | 1:3 |  |
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| 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