| 2. Round | 12/08/2023 | Alloa Athletic | - | Stirling Albion FC | 0:1 | ||||
| 3. Round | 19/08/2023 | Kelty Hearts | - | Alloa Athletic | 2:1 | ||||
| 5. Round | 02/09/2023 | Alloa Athletic | - | Cove Rangers | 1:0 | ||||
| 6. Round | 16/09/2023 | Hamilton Academical | - | Alloa Athletic | 2:1 |  |
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| 7. Round | 23/09/2023 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
| 8. Round | 30/09/2023 | Alloa Athletic | - | Edinburgh City | 1:1 | ||||
| 24. Round | 10/02/2024 | Alloa Athletic | - | Stirling Albion FC | 1:0 | ||||
| 15. Round | 13/02/2024 | Alloa Athletic | - | Annan Athletic | 2:1 | ||||
| 28. Round | 09/03/2024 | Alloa Athletic | - | Kelty Hearts | 3:0 | ||||
| 29. Round | 16/03/2024 | Edinburgh City | - | Alloa Athletic | 2:5 | |
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| 19. Round | 19/03/2024 | Kelty Hearts | - | Alloa Athletic | 2:1 | ||||
| 30. Round | 23/03/2024 | Alloa Athletic | - | Queen Of The South | 0:2 | ||||
| 34. Round | 20/04/2024 | Cove Rangers | - | Alloa Athletic | 2:3 | ||||
| 36. Round | 04/05/2024 | Falkirk FC | - | Alloa Athletic | 2:2 |  |
Scotland