| 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 | |
Schottland