| League Two | 28/08/21 | Cowdenbeath FC | - | Annan Athletic | 1:3 |  |
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| League Two | 30/10/21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
| League Two | 08/01/22 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
| League Two | 09/04/22 | Annan Athletic | - | Cowdenbeath FC | 2:3 | ||||
| League One | 23/09/23 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
| League One | 03/02/24 | Annan Athletic | - | Alloa Athletic | 2:3 | ||||
| League One | 30/03/24 | Alloa Athletic | - | Annan Athletic | 1:1 | |
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| League One | 21/09/24 | Arbroath FC | - | Annan Athletic | 2:0 | ||||
| League One | 21/12/24 | Annan Athletic | - | Arbroath FC | 0:4 | |
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| League One | 15/02/25 | Cove Rangers | - | Annan Athletic | 3:1 | ||||
| League One | 03/05/25 | Annan Athletic | - | Cove Rangers | 2:4 |
Scotland