| 22. Round | 27/01/2024 | Annan Athletic | - | Edinburgh City | 3:0 | ||||
| 23. Round | 03/02/2024 | Annan Athletic | - | Alloa Athletic | 2:3 | ||||
| 24. Round | 10/02/2024 | Hamilton Academical | - | Annan Athletic | 2:3 |  |
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| 15. Round | 13/02/2024 | Alloa Athletic | - | Annan Athletic | 2:1 | ||||
| 25. Round | 17/02/2024 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| 26. Round | 24/02/2024 | Cove Rangers | - | Annan Athletic | 2:1 | ||||
| 27. Round | 02/03/2024 | Falkirk FC | - | Annan Athletic | 1:1 | ||||
| 29. Round | 16/03/2024 | Montrose FC | - | Annan Athletic | 1:1 |  |
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| 30. Round | 23/03/2024 | Annan Athletic | - | Kelty Hearts | 3:2 | ||||
| 31. Round | 30/03/2024 | Alloa Athletic | - | Annan Athletic | 1:1 | ||||
| 32. Round | 06/04/2024 | Annan Athletic | - | Hamilton Academical | 1:3 | ||||
| 33. Round | 13/04/2024 | Annan Athletic | - | Cove Rangers | 4:2 | |
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| 34. Round | 20/04/2024 | Edinburgh City | - | Annan Athletic | 1:2 | ||||
| 35. Round | 27/04/2024 | Annan Athletic | - | Falkirk FC | 3:3 | ||||
| 36. Round | 04/05/2024 | Stirling Albion FC | - | Annan Athletic | 1:1 |
Scotland