| 16. Ronde | 09.12.2023 | Montrose FC | - | Queen Of The South | 1:4 | ||||
| 20. Ronde | 06.01.2024 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| 21. Ronde | 13.01.2024 | Montrose FC | - | Stirling Albion FC | 0:1 |  |
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| 22. Ronde | 27.01.2024 | Hamilton Academical | - | Montrose FC | 1:1 | ||||
| 15. Ronde | 06.02.2024 | Stirling Albion FC | - | Montrose FC | 0:2 | ||||
| 24. Ronde | 10.02.2024 | Montrose FC | - | Edinburgh City | 3:0 | ||||
| 25. Ronde | 17.02.2024 | Montrose FC | - | Kelty Hearts | 4:2 | ||||
| 23. Ronde | 20.02.2024 | Falkirk FC | - | Montrose FC | 3:0 | |
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| 26. Ronde | 24.02.2024 | Queen Of The South | - | Montrose FC | 2:3 | ||||
| 27. Ronde | 02.03.2024 | Montrose FC | - | Alloa Athletic | 4:3 | ||||
| 30. Ronde | 23.03.2024 | Stirling Albion FC | - | Montrose FC | 1:0 | ||||
| 31. Ronde | 30.03.2024 | Montrose FC | - | Falkirk FC | 1:7 | ||||
| 32. Ronde | 16.04.2024 | Edinburgh City | - | Montrose FC | 1:0 | ||||
| 35. Ronde | 27.04.2024 | Kelty Hearts | - | Montrose FC | 0:2 | ||||
| 36. Ronde | 04.05.2024 | Montrose FC | - | Queen Of The South | 3:2 |
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