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