| League One | 26.08.23 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
| League One | 28.10.23 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| League One | 27.01.24 | Annan Athletic | - | Edinburgh City | 3:0 |  |
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| League One | 20.04.24 | Edinburgh City | - | Annan Athletic | 1:2 | ||||
| League One | 31.08.24 | Stenhousemuir FC | - | Annan Athletic | 5:1 | ||||
| League One | 09.11.24 | Annan Athletic | - | Stenhousemuir FC | 1:1 |
Schottland