| 1. Jornada | 05.08.2023 | Montrose FC | - | Kelty Hearts | 0:2 |  |
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| 2. Jornada | 12.08.2023 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| 3. Jornada | 19.08.2023 | Montrose FC | - | Cove Rangers | 0:3 | ||||
| 4. Jornada | 26.08.2023 | Hamilton Academical | - | Montrose FC | 1:0 | ||||
| 6. Jornada | 16.09.2023 | Montrose FC | - | Edinburgh City | 5:2 | ||||
| 7. Jornada | 23.09.2023 | Montrose FC | - | Stirling Albion FC | 1:0 | ||||
| 8. Jornada | 30.09.2023 | Falkirk FC | - | Montrose FC | 3:2 | ||||
| 36. Jornada | 04.05.2024 | Montrose FC | - | Queen Of The South | 3:2 |
Escocia