| 8. Round | 30/09/2023 | Alloa Athletic | - | Edinburgh City | 1:1 |  |
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| 9. Round | 07/10/2023 | Montrose FC | - | Alloa Athletic | 2:1 | |
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| 12. Round | 04/11/2023 | Stirling Albion FC | - | Alloa Athletic | 0:2 | |
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| 13. Round | 11/11/2023 | Alloa Athletic | - | Queen Of The South | 1:0 | |
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| 14. Round | 18/11/2023 | Edinburgh City | - | Alloa Athletic | 3:0 | ||||
| 16. Round | 09/12/2023 | Alloa Athletic | - | Hamilton Academical | 0:0 | ||||
| 20. Round | 06/01/2024 | Alloa Athletic | - | Edinburgh City | 3:1 | |
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| 21. Round | 13/01/2024 | Queen Of The South | - | Alloa Athletic | 1:1 | ||||
| 22. Round | 27/01/2024 | Alloa Athletic | - | Falkirk FC | 0:5 | ||||
| 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 | ||||
| 19. Round | 19/03/2024 | Kelty Hearts | - | Alloa Athletic | 2:1 | ||||
| 30. Round | 23/03/2024 | Alloa Athletic | - | Queen Of The South | 0:2 | ||||
| 35. Round | 27/04/2024 | Alloa Athletic | - | Hamilton Academical | 0:1 |  |
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| 36. Round | 04/05/2024 | Falkirk FC | - | Alloa Athletic | 2:2 |
Scotland