| 3. Jornada | 19.08.2023 | Montrose FC | - | Cove Rangers | 0:3 | ||||
| 5. Jornada | 02.09.2023 | Queen Of The South | - | Montrose FC | 2:3 | ||||
| 6. Jornada | 16.09.2023 | Montrose FC | - | Edinburgh City | 5:2 |  |
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| 7. Jornada | 23.09.2023 | Montrose FC | - | Stirling Albion FC | 1:0 | ||||
| 9. Jornada | 07.10.2023 | Montrose FC | - | Alloa Athletic | 2:1 | ||||
| 11. Jornada | 28.10.2023 | Montrose FC | - | Hamilton Academical | 0:3 |  |
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| 12. Jornada | 04.11.2023 | Edinburgh City | - | Montrose FC | 1:5 | |
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| 13. Jornada | 11.11.2023 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| 10. Jornada | 14.11.2023 | Cove Rangers | - | Montrose FC | 1:0 | ||||
| 14. Jornada | 28.11.2023 | Montrose FC | - | Falkirk FC | 0:0 | ||||
| 16. Jornada | 09.12.2023 | Montrose FC | - | Queen Of The South | 1:4 | |
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| 17. Jornada | 16.12.2023 | Kelty Hearts | - | Montrose FC | 0:1 |
Escocia