1. Round | 05/08/2023 | Montrose FC | - | Kelty Hearts | 0:2 | ||||
2. Round | 12/08/2023 | Annan Athletic | - | Montrose FC | 1:3 | ||||
3. Round | 19/08/2023 | Montrose FC | - | Cove Rangers | 0:3 | ||||
4. Round | 26/08/2023 | Hamilton Academical | - | Montrose FC | 1:0 | ||||
6. Round | 16/09/2023 | Montrose FC | - | Edinburgh City | 5:2 | ||||
7. Round | 23/09/2023 | Montrose FC | - | Stirling Albion FC | 1:0 | ||||
8. Round | 30/09/2023 | Falkirk FC | - | Montrose FC | 3:2 | ||||
36. Round | 04/05/2024 | Montrose FC | - | Queen Of The South | 3:2 |