| 1. Round | 05/08/2023 | Hamilton Academical | - | Cove Rangers | 1:0 | ||||
| 4. Round | 26/08/2023 | Hamilton Academical | - | Montrose FC | 1:0 | ||||
| 6. Round | 16/09/2023 | Hamilton Academical | - | Alloa Athletic | 2:1 | ||||
| 8. Round | 29/09/2023 | Hamilton Academical | - | Annan Athletic | 5:0 | ||||
| 11. Round | 28/10/2023 | Montrose FC | - | Hamilton Academical | 0:3 | ||||
| 13. Round | 11/11/2023 | Hamilton Academical | - | Stirling Albion FC | 5:0 | ||||
| 14. Round | 28/11/2023 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| 16. Round | 09/12/2023 | Alloa Athletic | - | Hamilton Academical | 0:0 | ||||
| 17. Round | 16/12/2023 | Hamilton Academical | - | Falkirk FC | 1:3 | ||||
| 18. Round | 23/12/2023 | Hamilton Academical | - | Kelty Hearts | 1:1 | ||||
| 19. Round | 30/12/2023 | Edinburgh City | - | Hamilton Academical | 2:5 |  |
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| 21. Round | 13/01/2024 | Hamilton Academical | - | Cove Rangers | 2:0 | ||||
| 22. Round | 27/01/2024 | Hamilton Academical | - | Montrose FC | 1:1 | ||||
| 28. Round | 09/03/2024 | Hamilton Academical | - | Edinburgh City | 1:0 | ||||
| 32. Round | 06/04/2024 | Annan Athletic | - | Hamilton Academical | 1:3 |  |
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| 36. Round | 04/05/2024 | Hamilton Academical | - | Kelty Hearts | 4:1 |
Scotland