| 5. Jornada | 31.08.2024 | Stenhousemuir FC | - | Annan Athletic | 5:1 | ||||
| 8. Jornada | 28.09.2024 | Kelty Hearts | - | Annan Athletic | 3:0 | ||||
| 21. Jornada | 18.01.2025 | Annan Athletic | - | Inverness CT | 0:3 | ||||
| 22. Jornada | 25.01.2025 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| 25. Jornada | 15.02.2025 | Cove Rangers | - | Annan Athletic | 3:1 | ||||
| 28. Jornada | 08.03.2025 | Annan Athletic | - | Stenhousemuir FC | 0:2 |  |
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| 29. Jornada | 15.03.2025 | Inverness CT | - | Annan Athletic | 0:1 | ||||
| 30. Jornada | 22.03.2025 | Montrose FC | - | Annan Athletic | 3:1 | ||||
| 31. Jornada | 29.03.2025 | Annan Athletic | - | Kelty Hearts | 2:1 | ||||
| 32. Jornada | 05.04.2025 | Annan Athletic | - | Queen Of The South | 0:2 | ||||
| 33. Jornada | 12.04.2025 | Alloa Athletic | - | Annan Athletic | 1:0 | ||||
| 34. Jornada | 19.04.2025 | Annan Athletic | - | Arbroath FC | 5:1 |
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