| 2. Round | 06/08/2022 | Montrose FC | - | Queen Of The South | 0:0 | ||||
| 12. Round | 22/10/2022 | Montrose FC | - | Dunfermline Athletic | 2:0 | ||||
| 13. Round | 29/10/2022 | Airdrieonians FC | - | Montrose FC | 4:0 | ||||
| 14. Round | 05/11/2022 | Montrose FC | - | Peterhead FC | 3:0 | ||||
| 15. Round | 12/11/2022 | Kelty Hearts | - | Montrose FC | 1:3 | ||||
| 16. Round | 19/11/2022 | Queen Of The South | - | Montrose FC | 4:0 | ||||
| 18. Round | 17/12/2022 | FC Edinburgh | - | Montrose FC | 2:2 |
Scotland