| 8. Round | 28/09/2024 | Kelty Hearts | - | Annan Athletic | 3:0 | ||||
| 9. Round | 05/10/2024 | Annan Athletic | - | Montrose FC | 1:0 |  |
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| 10. Round | 19/10/2024 | Inverness CT | - | Annan Athletic | 1:0 | ||||
| 11. Round | 26/10/2024 | Annan Athletic | - | Queen Of The South | 1:0 | ||||
| 12. Round | 02/11/2024 | Alloa Athletic | - | Annan Athletic | 5:0 | ||||
| 13. Round | 09/11/2024 | Annan Athletic | - | Stenhousemuir FC | 1:1 | ||||
| 14. Round | 16/11/2024 | Annan Athletic | - | Kelty Hearts | 0:2 | ||||
| 15. Round | 23/11/2024 | Montrose FC | - | Annan Athletic | 2:1 | ||||
| 16. Round | 07/12/2024 | Annan Athletic | - | Cove Rangers | 1:1 | ||||
| 17. Round | 14/12/2024 | Dumbarton FC | - | Annan Athletic | 1:5 | |
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| 18. Round | 21/12/2024 | Annan Athletic | - | Arbroath FC | 0:4 | ||||
| 19. Round | 28/12/2024 | Queen Of The South | - | Annan Athletic | 1:1 | ||||
| 20. Round | 04/01/2025 | Stenhousemuir FC | - | Annan Athletic | 1:1 | ||||
| 22. Round | 25/01/2025 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| 23. Round | 01/02/2025 | Kelty Hearts | - | Annan Athletic | 1:3 | ||||
| 24. Round | 08/02/2025 | Annan Athletic | - | Dumbarton FC | 2:1 | ||||
| 25. Round | 15/02/2025 | Cove Rangers | - | Annan Athletic | 3:1 |
Scotland