| 5. Round | 31/08/2024 | Stenhousemuir FC | - | Annan Athletic | 5:1 | ||||
| 8. Round | 28/09/2024 | Kelty Hearts | - | Annan Athletic | 3:0 | ||||
| 21. Round | 18/01/2025 | Annan Athletic | - | Inverness CT | 0:3 | ||||
| 22. Round | 25/01/2025 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| 25. Round | 15/02/2025 | Cove Rangers | - | Annan Athletic | 3:1 | ||||
| 28. Round | 08/03/2025 | Annan Athletic | - | Stenhousemuir FC | 0:2 |  |
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| 29. Round | 15/03/2025 | Inverness CT | - | Annan Athletic | 0:1 | ||||
| 30. Round | 22/03/2025 | Montrose FC | - | Annan Athletic | 3:1 | ||||
| 31. Round | 29/03/2025 | Annan Athletic | - | Kelty Hearts | 2:1 | ||||
| 32. Round | 05/04/2025 | Annan Athletic | - | Queen Of The South | 0:2 | ||||
| 33. Round | 12/04/2025 | Alloa Athletic | - | Annan Athletic | 1:0 | ||||
| 34. Round | 19/04/2025 | Annan Athletic | - | Arbroath FC | 5:1 | ||||
| 35. Round | 26/04/2025 | Dumbarton FC | - | Annan Athletic | 3:1 |
Scotland