| 20. Round | 06/01/2024 | Alloa Athletic | - | Edinburgh City | 3:1 | ||||
| 22. Round | 27/01/2024 | Alloa Athletic | - | Falkirk FC | 0:5 | ||||
| 24. Round | 10/02/2024 | Alloa Athletic | - | Stirling Albion FC | 1:0 | ||||
| 26. Round | 24/02/2024 | Hamilton Academical | - | Alloa Athletic | 1:2 |  |
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| 29. Round | 16/03/2024 | Edinburgh City | - | Alloa Athletic | 2:5 | ||||
| 30. Round | 23/03/2024 | Alloa Athletic | - | Queen Of The South | 0:2 | ||||
| 31. Round | 30/03/2024 | Alloa Athletic | - | Annan Athletic | 1:1 | ||||
| 32. Round | 06/04/2024 | Stirling Albion FC | - | Alloa Athletic | 1:5 | ||||
| 35. Round | 27/04/2024 | Alloa Athletic | - | Hamilton Academical | 0:1 |
Scotland