| League Two | 25.09.21 | Annan Athletic | - | Edinburgh City FC | 1:3 | ||||
| League Two | 03.12.21 | Edinburgh City FC | - | Annan Athletic | 0:1 | ||||
| League Two | 19.02.22 | Annan Athletic | - | Edinburgh City FC | 2:1 | ||||
| League Two | 22.04.22 | Edinburgh City FC | - | Annan Athletic | 2:1 | ||||
| Playoffs | 10.05.22 | Edinburgh City FC | - | Annan Athletic | 2:0 |  |
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| Playoffs | 13.05.22 | Annan Athletic | - | Edinburgh City FC | 2:1 | |
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| League One | 26.08.23 | Annan Athletic | - | Edinburgh City | 3:2 | |
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| League One | 28.10.23 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| League Cup | 20.07.24 | Arbroath FC | - | Annan Athletic | 0:3 | ||||
| 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 | 01.03.25 | Arbroath FC | - | Annan Athletic | 3:0 | ||||
| League One | 19.04.25 | Annan Athletic | - | Arbroath FC | 5:1 |
Schottland