| League Two | 18/09/21 | Elgin City | - | Annan Athletic | 0:2 | ||||
| League Two | 11/12/21 | Annan Athletic | - | Elgin City | 4:1 | ||||
| League Two | 15/02/22 | Elgin City | - | Annan Athletic | 0:2 | ||||
| League Two | 12/03/22 | Annan Athletic | - | Elgin City | 2:1 |  |
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| League Cup | 16/07/22 | Annan Athletic | - | Elgin City | 4:0 | ||||
| League Two | 01/10/22 | Elgin City | - | Annan Athletic | 5:1 | |
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| League Two | 19/11/22 | Annan Athletic | - | Elgin City | 1:3 |  |
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| League Two | 14/01/23 | Elgin City | - | Annan Athletic | 1:1 | |
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| League Two | 11/03/23 | Annan Athletic | - | Elgin City | 4:1 | |
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| League One | 12/08/23 | Annan Athletic | - | Montrose FC | 1:3 | |
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| League One | 11/11/23 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| League One | 06/01/24 | Annan Athletic | - | Montrose FC | 2:2 |  |
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| League One | 16/03/24 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| League One | 05/10/24 | Annan Athletic | - | Montrose FC | 1:0 | |
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| League One | 23/11/24 | Montrose FC | - | Annan Athletic | 2:1 | ||||
| Playoffs | 06/05/25 | Elgin City | - | Annan Athletic | 2:4 | ||||
| Playoffs | 10/05/25 | Annan Athletic | - | Elgin City | 1:2 | |
Scotland