| East Fife FC v Montrose FC 13/04/2019 | View match | |
| Montrose FC v Airdrieonians (Old) 20/04/2019 | View match | |
| Forfar Athletic FC v Montrose FC 27/04/2019 | View match | |
| Montrose FC v Raith Rovers FC 04/05/2019 | View match | |
| Stranraer v Montrose FC 03/08/2019 | View match | |
| Montrose FC v Airdrieonians (Old) 10/08/2019 | View match | |
| Falkirk FC v Montrose FC 17/08/2019 | View match | |
| Raith Rovers FC v Montrose FC 24/08/2019 | View match | |
| Montrose FC v Dumbarton 31/08/2019 | View match | |
| Montrose FC v East Fife FC 14/09/2019 | View match | |
| Forfar Athletic FC v Montrose FC 21/09/2019 | View match | |
| Montrose FC v Peterhead 28/09/2019 | View match |