| 1 | 2/2/2019 | 1-1 v Forfar AthleticRaith Rovers 1-1 Forfar Athletic | Ladbrokes League One |
| 2 | 9/2/2019 | 1-3 v HibernianHibernian 3-1 Raith Rovers | William Hill Scottish Cup Fifth Round |
| 3 | 16/2/2019 | 0-1 v ArbroathRaith Rovers 0-1 Arbroath | Ladbrokes League One |
| 4 | 23/2/2019 | 4-1 v MontroseRaith Rovers 4-1 Montrose | Ladbrokes League One |
| 5 | 26/2/2019 | 2-2 v DumbartonDumbarton 2-2 Raith Rovers | Ladbrokes League One |
| 6 | 2/3/2019 | 2-2 v StranraerStranraer 2-2 Raith Rovers | Ladbrokes League One |
| 7 | 9/3/2019 | 1-0 v AirdrieoniansRaith Rovers 1-0 Airdrieonians | Ladbrokes League One |
| 8 | 16/3/2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Raith Rovers | Ladbrokes League One |
| 9 | 23/3/2019 | 4-1 v DumbartonRaith Rovers 4-1 Dumbarton | Ladbrokes League One |
| 10 | 6/4/2019 | 1-1 v StenhousemuirStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 11 | 13/4/2019 | 2-3 v StranraerRaith Rovers 2-3 Stranraer | Ladbrokes League One |
| 12 | 21/4/2019 | 2-2 v ArbroathArbroath 2-2 Raith Rovers | Ladbrokes League One |
| 13 | 27/4/2019 | 3-2 v Brechin CityRaith Rovers 3-2 Brechin City | Ladbrokes League One |
| 14 | 4/5/2019 | 1-1 v MontroseMontrose 1-1 Raith Rovers | Ladbrokes League One |
| 15 | 7/5/2019 | 2-1 v Forfar AthleticRaith Rovers 2-1 Forfar Athletic | Ladbrokes League One Play-off |
| 16 | 11/5/2019 | 1-1 v Forfar AthleticForfar Athletic 1-1 Raith Rovers | Ladbrokes League One Play-off |
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