| 20. Round | 02/01/2022 | East Fife FC | - | Montrose FC | 0:2 | ||||
| 21. Round | 08/01/2022 | Montrose FC | - | Alloa Athletic | 1:1 | ||||
| 22. Round | 15/01/2022 | Cove Rangers | - | Montrose FC | 1:0 |  |
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| 23. Round | 29/01/2022 | Montrose FC | - | Falkirk FC | 2:1 | ||||
| 24. Round | 05/02/2022 | Montrose FC | - | Dumbarton FC | 1:1 | ||||
| 25. Round | 12/02/2022 | Airdrieonians FC | - | Montrose FC | 4:1 | ||||
| 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 | ||||
| 29. Round | 12/03/2022 | Peterhead FC | - | Montrose FC | 0:1 | ||||
| 30. Round | 19/03/2022 | Montrose FC | - | Cove Rangers | 1:2 | ||||
| 31. Round | 26/03/2022 | Dumbarton FC | - | Montrose FC | 0:0 |  |
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| 36. Round | 30/04/2022 | Alloa Athletic | - | Montrose FC | 4:1 |
England