| League Two | 02/10/21 | Kelty Hearts | - | Annan Athletic | 2:1 |  |
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| League Two | 26/12/21 | Annan Athletic | - | Kelty Hearts | 5:1 | ||||
| League Two | 26/02/22 | Kelty Hearts | - | Annan Athletic | 3:1 | |
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| League Two | 30/04/22 | Annan Athletic | - | Kelty Hearts | 1:2 | ||||
| League One | 29/09/23 | Hamilton Academical | - | Annan Athletic | 5:0 | |
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| League One | 28/11/23 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| League One | 10/02/24 | Hamilton Academical | - | Annan Athletic | 2:3 |
England