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