| Raith Rovers FC v Falkirk FC 05/10/2019 | View match | |
| Clyde v Raith Rovers FC 19/10/2019 | View match | |
| Raith Rovers FC v East Fife FC 26/10/2019 | View match | |
| Peterhead v Raith Rovers FC 02/11/2019 | View match | |
| Raith Rovers FC v Stranraer 09/11/2019 | View match | |
| Raith Rovers FC v Elgin City FC 15/11/2019 | View match | |
| Raith Rovers FC v Peterhead 23/11/2019 | View match | |
| Raith Rovers FC v Forfar Athletic FC 26/11/2019 | View match | |
| Montrose FC v Raith Rovers FC 30/11/2019 | View match | |
| Raith Rovers FC v Airdrieonians (Old) 07/12/2019 | View match | |
| Falkirk FC v Raith Rovers FC 14/12/2019 | View match | |
| Raith Rovers FC v Dumbarton 21/12/2019 | View match |