| League One | 02/09/23 | Kelty Hearts | - | Annan Athletic | 1:1 |  |
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| League One | 04/11/23 | Annan Athletic | - | Kelty Hearts | 2:2 | ||||
| League One | 13/01/24 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| League One | 23/03/24 | Annan Athletic | - | Kelty Hearts | 3:2 | ||||
| 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 | ||||
| League One | 05/04/25 | Annan Athletic | - | Queen Of The South | 0:2 |
Scotland