| Clyde v Montrose FC 05/10/2019 | View match | |
| Airdrieonians (Old) v Montrose FC 19/10/2019 | View match | |
| Montrose FC v Stranraer 26/10/2019 | View match | |
| East Fife FC v Montrose FC 02/11/2019 | View match | |
| Montrose FC v Forfar Athletic FC 09/11/2019 | View match | |
| Peterhead v Montrose FC 16/11/2019 | View match | |
| Bonnyrigg Rose Athletic v Montrose FC 23/11/2019 | View match | |
| Montrose FC v Raith Rovers FC 30/11/2019 | View match | |
| Dumbarton v Montrose FC 07/12/2019 | View match | |
| Montrose FC v Clyde 14/12/2019 | View match | |
| Montrose FC v Falkirk FC 21/12/2019 | View match | |
| Forfar Athletic FC v Montrose FC 28/12/2019 | View match |