| 1. Round | 31/07/2021 | Airdrieonians FC | - | Montrose FC | 0:3 | ||||
| 8. Round | 25/09/2021 | Montrose FC | - | Falkirk FC | 2:2 | ||||
| 11. Round | 23/10/2021 | Montrose FC | - | East Fife FC | 4:1 | ||||
| 12. Round | 30/10/2021 | Peterhead FC | - | Montrose FC | 0:0 | ||||
| 13. Round | 06/11/2021 | Montrose FC | - | Cove Rangers | 0:0 | ||||
| 14. Round | 13/11/2021 | Alloa Athletic | - | Montrose FC | 2:2 | ||||
| 15. Round | 20/11/2021 | Falkirk FC | - | Montrose FC | 0:1 | ||||
| 16. Round | 07/12/2021 | Montrose FC | - | Airdrieonians FC | 2:1 |  |
|||
| 19. Round | 22/12/2021 | Montrose FC | - | Peterhead FC | 2:0 | ||||
| 22. Round | 15/01/2022 | Cove Rangers | - | Montrose FC | 1:0 | ||||
| 23. Round | 29/01/2022 | Montrose FC | - | Falkirk FC | 2:1 | ||||
| 24. Round | 05/02/2022 | Montrose FC | - | Dumbarton FC | 1:1 | ||||
| 26. Round | 19/02/2022 | Montrose FC | - | Clyde FC | 1:1 | |
|||
| 27. Round | 26/02/2022 | Queen's Park FC | - | Montrose FC | 0:1 |  |
|||
| 28. Round | 05/03/2022 | Montrose FC | - | East Fife FC | 0:0 |  |
|||
| 32. Round | 02/04/2022 | Falkirk FC | - | Montrose FC | 0:3 |
Scotland