| Montrose FC v Dundee United FC 19/01/2019 | View match | |
| Dumbarton v Montrose FC 26/01/2019 | View match | |
| Montrose FC v Brechin City FC 02/02/2019 | View match | |
| Stenhousemuir FC v Montrose FC 09/02/2019 | View match | |
| Montrose FC v Forfar Athletic FC 16/02/2019 | View match | |
| Raith Rovers FC v Montrose FC 23/02/2019 | View match | |
| Airdrieonians (Old) v Montrose FC 02/03/2019 | View match | |
| Montrose FC v Dumbarton 09/03/2019 | View match | |
| Montrose FC v Stenhousemuir FC 23/03/2019 | View match | |
| Montrose FC v Stranraer 30/03/2019 | View match | |
| Brechin City FC v Montrose FC 02/04/2019 | View match | |
| Arbroath FC v Montrose FC 06/04/2019 | View match |