All countries
| 16. Round | Kelty Hearts | Montrose | details | 06.12.2025 16:00 | |||
| 1/32-finals | Benburb | Montrose | 0:3 (0:2, 0:1) | details | 29.11.2025 | |||
| 15. Round | Montrose | East Fife | 2:1 (2:1, 0:0) | details | 22.11.2025 | |||
| 6. Round | Montrose | Hibernian B | 4:4 (2:3, 2:1) | details | 17.11.2025 | |||
| 14. Round | Peterhead | Montrose | 1:1 (0:0, 1:1) | details | 15.11.2025 | |||
| 13. Round | Montrose | Alloa | 0:4 (0:1, 0:3) | details | 08.11.2025 | |||
| 16. Round | Kelty Hearts | Montrose | details | 06.12.2025 16:00 | |||
| 1/16-finals | Montrose | Spartans | details | 09.12.2025 20:45 | |||
| 17. Round | Montrose | Stenhousemuir | details | 13.12.2025 16:00 | |||
| 18. Round | Queen of South | Montrose | details | 20.12.2025 16:00 | |||
| 19. Round | Montrose | Inverness | details | 27.12.2025 16:00 | |||