| 5. Jornada | 31.08.2024 | Stenhousemuir FC | - | Annan Athletic | 5:1 | ||||
| 6. Jornada | 14.09.2024 | Annan Athletic | - | Dumbarton FC | 1:1 | ||||
| 7. Jornada | 21.09.2024 | Arbroath FC | - | Annan Athletic | 2:0 | ||||
| 8. Jornada | 28.09.2024 | Kelty Hearts | - | Annan Athletic | 3:0 | ||||
| 9. Jornada | 05.10.2024 | Annan Athletic | - | Montrose FC | 1:0 | ||||
| 13. Jornada | 09.11.2024 | Annan Athletic | - | Stenhousemuir FC | 1:1 | ||||
| 14. Jornada | 16.11.2024 | Annan Athletic | - | Kelty Hearts | 0:2 |
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