| 1 | 6/10/2018 | 1-1 v ArbroathRaith Rovers 1-1 Arbroath | Ladbrokes League One |
| 2 | 20/10/2018 | 2-1 v StranraerRaith Rovers 2-1 Stranraer | Ladbrokes League One |
| 3 | 27/10/2018 | 2-3 v Forfar AthleticForfar Athletic 3-2 Raith Rovers | Ladbrokes League One |
| 4 | 3/11/2018 | 2-1 v Brechin CityRaith Rovers 2-1 Brechin City | Ladbrokes League One |
| 5 | 10/11/2018 | 1-2 v East FifeEast Fife 2-1 Raith Rovers | Ladbrokes League One |
| 6 | 17/11/2018 | 3-1 v StenhousemuirStenhousemuir 1-3 Raith Rovers | Ladbrokes League One |
| 7 | 5/1/2019 | 5-1 v StenhousemuirRaith Rovers 5-1 Stenhousemuir | Ladbrokes League One |
| 8 | 12/1/2019 | 1-1 v AirdrieoniansAirdrieonians 1-1 Raith Rovers | Ladbrokes League One |
| 9 | 19/1/2019 | 3-0 v Dunfermline AthleticRaith Rovers 3-0 Dunfermline Athletic | William Hill Scottish Cup Fourth Round |
| 10 | 26/1/2019 | 1-2 v Brechin CityBrechin City 2-1 Raith Rovers | Ladbrokes League One |
| 11 | 16/2/2019 | 0-1 v ArbroathRaith Rovers 0-1 Arbroath | Ladbrokes League One |
| 12 | 23/2/2019 | 4-1 v MontroseRaith Rovers 4-1 Montrose | Ladbrokes League One |
| 13 | 26/2/2019 | 2-2 v DumbartonDumbarton 2-2 Raith Rovers | Ladbrokes League One |
| 14 | 2/3/2019 | 2-2 v StranraerStranraer 2-2 Raith Rovers | Ladbrokes League One |
| 15 | 9/3/2019 | 1-0 v AirdrieoniansRaith Rovers 1-0 Airdrieonians | Ladbrokes League One |
| 16 | 16/3/2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Raith Rovers | Ladbrokes League One |
| 17 | 23/3/2019 | 4-1 v DumbartonRaith Rovers 4-1 Dumbarton | Ladbrokes League One |
| 18 | 6/4/2019 | 1-1 v StenhousemuirStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 19 | 13/4/2019 | 2-3 v StranraerRaith Rovers 2-3 Stranraer | Ladbrokes League One |
| 20 | 21/4/2019 | 2-2 v ArbroathArbroath 2-2 Raith Rovers | Ladbrokes League One |
| 21 | 27/4/2019 | 3-2 v Brechin CityRaith Rovers 3-2 Brechin City | Ladbrokes League One |
| 22 | 4/5/2019 | 1-1 v MontroseMontrose 1-1 Raith Rovers | Ladbrokes League One |
| 23 | 7/5/2019 | 2-1 v Forfar AthleticRaith Rovers 2-1 Forfar Athletic | Ladbrokes League One Play-off |
| 24 | 11/5/2019 | 1-1 v Forfar AthleticForfar Athletic 1-1 Raith Rovers | Ladbrokes League One Play-off |
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