| 1 | Sat 28 Jul 2018 | 0-2 v Cove RangersCove Rangers 2-0 Raith Rovers | Betfred Cup Group C |
| 2 | Sat 4 Aug 2018 | 1-1 v StranraerStranraer 1-1 Raith Rovers | Ladbrokes League One |
| 3 | Sat 11 Aug 2018 | 2-0 v StenhousemuirRaith Rovers 2-0 Stenhousemuir | Ladbrokes League One |
| 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 6 Oct 2018 | 1-1 v ArbroathRaith Rovers 1-1 Arbroath | Ladbrokes League One |
| 10 | Sat 20 Oct 2018 | 2-1 v StranraerRaith Rovers 2-1 Stranraer | Ladbrokes League One |
| 11 | Sat 27 Oct 2018 | 2-3 v Forfar AthleticForfar Athletic 3-2 Raith Rovers | Ladbrokes League One |
| 12 | Sat 3 Nov 2018 | 2-1 v Brechin CityRaith Rovers 2-1 Brechin City | Ladbrokes League One |
| 13 | Sat 10 Nov 2018 | 1-2 v East FifeEast Fife 2-1 Raith Rovers | Ladbrokes League One |
| 14 | Sat 24 Nov 2018 | 3-0 v Queens ParkQueens Park 0-3 Raith Rovers | William Hill Scottish Cup Third Round |
| 15 | Sat 1 Dec 2018 | 2-0 v AirdrieoniansRaith Rovers 2-0 Airdrieonians | Ladbrokes League One |
| 16 | Sat 8 Dec 2018 | 2-3 v MontroseMontrose 3-2 Raith Rovers | Ladbrokes League One |
| 17 | Sat 15 Dec 2018 | 4-2 v DumbartonRaith Rovers 4-2 Dumbarton | Ladbrokes League One |
| 18 | Sat 22 Dec 2018 | 2-0 v ArbroathArbroath 0-2 Raith Rovers | Ladbrokes League One |
| 19 | Sat 29 Dec 2018 | 1-2 v East FifeRaith Rovers 1-2 East Fife | Ladbrokes League One |
| 20 | Sat 5 Jan 2019 | 5-1 v StenhousemuirRaith Rovers 5-1 Stenhousemuir | Ladbrokes League One |
| 21 | Sat 12 Jan 2019 | 1-1 v AirdrieoniansAirdrieonians 1-1 Raith Rovers | Ladbrokes League One |
| 22 | Sat 19 Jan 2019 | 3-0 v Dunfermline AthleticRaith Rovers 3-0 Dunfermline Athletic | William Hill Scottish Cup Fourth Round |
| 23 | Sat 26 Jan 2019 | 1-2 v Brechin CityBrechin City 2-1 Raith Rovers | Ladbrokes League One |
| 24 | Sat 2 Feb 2019 | 1-1 v Forfar AthleticRaith Rovers 1-1 Forfar Athletic | Ladbrokes League One |
| 25 | Sat 9 Feb 2019 | 1-3 v HibernianHibernian 3-1 Raith Rovers | William Hill Scottish Cup Fifth Round |
| 26 | Sat 16 Feb 2019 | 0-1 v ArbroathRaith Rovers 0-1 Arbroath | Ladbrokes League One |
| 27 | Sat 23 Feb 2019 | 4-1 v MontroseRaith Rovers 4-1 Montrose | Ladbrokes League One |
| 28 | Tue 26 Feb 2019 | 2-2 v DumbartonDumbarton 2-2 Raith Rovers | Ladbrokes League One |
| 29 | Sat 9 Mar 2019 | 1-0 v AirdrieoniansRaith Rovers 1-0 Airdrieonians | Ladbrokes League One |
| 30 | Sat 16 Mar 2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Raith Rovers | Ladbrokes League One |
| 31 | Sat 23 Mar 2019 | 4-1 v DumbartonRaith Rovers 4-1 Dumbarton | Ladbrokes League One |
| 32 | Sat 6 Apr 2019 | 1-1 v StenhousemuirStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 33 | Sat 13 Apr 2019 | 2-3 v StranraerRaith Rovers 2-3 Stranraer | Ladbrokes League One |
| 34 | Sat 27 Apr 2019 | 3-2 v Brechin CityRaith Rovers 3-2 Brechin City | Ladbrokes League One |
| 35 | Sat 4 May 2019 | 1-1 v MontroseMontrose 1-1 Raith Rovers | Ladbrokes League One |
| 36 | Tue 7 May 2019 | 2-1 v Forfar AthleticRaith Rovers 2-1 Forfar Athletic | Ladbrokes League One Play-off |
| 37 | Sat 11 May 2019 | 1-1 v Forfar AthleticForfar Athletic 1-1 Raith Rovers | Ladbrokes League One Play-off |
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