| 1 | Sat 14 Jul 2018 | 0-2 v CowdenbeathRaith Rovers 0-2 Cowdenbeath | Betfred Cup Group C |
| 2 | Sat 21 Jul 2018 | 1-1 v Heart of MidlothianRaith Rovers 1-1 Heart of Midlothian | Betfred Cup Group C |
| 3 | Sat 28 Jul 2018 | 0-2 v Cove RangersCove Rangers 2-0 Raith Rovers | Betfred Cup Group C |
| 4 | Sat 25 Aug 2018 | 4-3 v AirdrieoniansAirdrieonians 3-4 Raith Rovers | Ladbrokes League One |
| 5 | Sat 1 Sep 2018 | 4-0 v Forfar AthleticRaith Rovers 4-0 Forfar Athletic | Ladbrokes League One |
| 6 | Sat 8 Sep 2018 | 0-5 v Ross CountyRoss County 5-0 Raith Rovers | IRN-BRU Cup Second Round |
| 7 | Sat 15 Sep 2018 | 1-1 v Brechin CityBrechin City 1-1 Raith Rovers | Ladbrokes League One |
| 8 | Sat 22 Sep 2018 | 1-1 v MontroseRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 9 | Sat 1 Dec 2018 | 2-0 v AirdrieoniansRaith Rovers 2-0 Airdrieonians | Ladbrokes League One |
| 10 | Sat 8 Dec 2018 | 2-3 v MontroseMontrose 3-2 Raith Rovers | Ladbrokes League One |
| 11 | Sat 15 Dec 2018 | 4-2 v DumbartonRaith Rovers 4-2 Dumbarton | Ladbrokes League One |
| 12 | Sat 22 Dec 2018 | 2-0 v ArbroathArbroath 0-2 Raith Rovers | Ladbrokes League One |
| 13 | Sat 29 Dec 2018 | 1-2 v East FifeRaith Rovers 1-2 East Fife | Ladbrokes League One |
| 14 | Sat 5 Jan 2019 | 5-1 v StenhousemuirRaith Rovers 5-1 Stenhousemuir | Ladbrokes League One |
| 15 | Sat 12 Jan 2019 | 1-1 v AirdrieoniansAirdrieonians 1-1 Raith Rovers | Ladbrokes League One |
| 16 | Sat 19 Jan 2019 | 3-0 v Dunfermline AthleticRaith Rovers 3-0 Dunfermline Athletic | William Hill Scottish Cup Fourth Round |
| 17 | Sat 26 Jan 2019 | 1-2 v Brechin CityBrechin City 2-1 Raith Rovers | Ladbrokes League One |
| 18 | Sat 2 Feb 2019 | 1-1 v Forfar AthleticRaith Rovers 1-1 Forfar Athletic | Ladbrokes League One |
| 19 | Sat 9 Feb 2019 | 1-3 v HibernianHibernian 3-1 Raith Rovers | William Hill Scottish Cup Fifth Round |
| 20 | Sun 21 Apr 2019 | 2-2 v ArbroathArbroath 2-2 Raith Rovers | Ladbrokes League One |
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