| 1 | Sat 1 Sep 2018 | 4-0 v Forfar AthleticRaith Rovers 4-0 Forfar Athletic | Ladbrokes League One |
| 2 | Sat 8 Sep 2018 | 0-5 v Ross CountyRoss County 5-0 Raith Rovers | IRN-BRU Cup Second Round |
| 3 | Sat 15 Sep 2018 | 1-1 v Brechin CityBrechin City 1-1 Raith Rovers | Ladbrokes League One |
| 4 | Sat 22 Sep 2018 | 1-1 v MontroseRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 5 | Sat 6 Oct 2018 | 1-1 v ArbroathRaith Rovers 1-1 Arbroath | Ladbrokes League One |
| 6 | Sat 15 Dec 2018 | 4-2 v DumbartonRaith Rovers 4-2 Dumbarton | Ladbrokes League One |
| 7 | Sat 22 Dec 2018 | 2-0 v ArbroathArbroath 0-2 Raith Rovers | Ladbrokes League One |
| 8 | Sat 29 Dec 2018 | 1-2 v East FifeRaith Rovers 1-2 East Fife | Ladbrokes League One |
| 9 | Sat 5 Jan 2019 | 5-1 v StenhousemuirRaith Rovers 5-1 Stenhousemuir | Ladbrokes League One |
| 10 | Sat 12 Jan 2019 | 1-1 v AirdrieoniansAirdrieonians 1-1 Raith Rovers | Ladbrokes League One |
| 11 | Sat 19 Jan 2019 | 3-0 v Dunfermline AthleticRaith Rovers 3-0 Dunfermline Athletic | William Hill Scottish Cup Fourth Round |
| 12 | Sat 26 Jan 2019 | 1-2 v Brechin CityBrechin City 2-1 Raith Rovers | Ladbrokes League One |
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