| 7. Jornada | 23.09.2023 | Montrose FC | - | Stirling Albion FC | 1:0 |  |
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| 9. Jornada | 07.10.2023 | Montrose FC | - | Alloa Athletic | 2:1 | ||||
| 11. Jornada | 28.10.2023 | Montrose FC | - | Hamilton Academical | 0:3 | ||||
| 12. Jornada | 04.11.2023 | Edinburgh City | - | Montrose FC | 1:5 | ||||
| 13. Jornada | 11.11.2023 | Montrose FC | - | Annan Athletic | 1:1 |  |
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| 10. Jornada | 14.11.2023 | Cove Rangers | - | Montrose FC | 1:0 | ||||
| 18. Jornada | 23.12.2023 | Alloa Athletic | - | Montrose FC | 2:2 | ||||
| 19. Jornada | 30.12.2023 | Montrose FC | - | Cove Rangers | 1:1 | ||||
| 20. Jornada | 06.01.2024 | Annan Athletic | - | Montrose FC | 2:2 | |
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