| 1 | 14/7/2018 | 0-2 v CowdenbeathRaith Rovers 0-2 Cowdenbeath | Betfred Cup Group C |
| 2 | 21/7/2018 | 1-1 v Heart of MidlothianRaith Rovers 1-1 Heart of Midlothian | Betfred Cup Group C |
| 3 | 24/7/2018 | 1-2 v Inverness Caledonian ThistleInverness Caledonian Thistle 2-1 Raith Rovers | Betfred Cup Group C |
| 4 | 28/7/2018 | 0-2 v Cove RangersCove Rangers 2-0 Raith Rovers | Betfred Cup Group C |
| 5 | 4/8/2018 | 1-1 v StranraerStranraer 1-1 Raith Rovers | Ladbrokes League One |
| 6 | 11/8/2018 | 2-0 v StenhousemuirRaith Rovers 2-0 Stenhousemuir | Ladbrokes League One |
| 7 | 25/8/2018 | 4-3 v AirdrieoniansAirdrieonians 3-4 Raith Rovers | Ladbrokes League One |
| 8 | 1/9/2018 | 4-0 v Forfar AthleticRaith Rovers 4-0 Forfar Athletic | Ladbrokes League One |
| 9 | 8/9/2018 | 0-5 v Ross CountyRoss County 5-0 Raith Rovers | IRN-BRU Cup Second Round |
| 10 | 15/9/2018 | 1-1 v Brechin CityBrechin City 1-1 Raith Rovers | Ladbrokes League One |
| 11 | 22/9/2018 | 1-1 v MontroseRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 12 | 6/10/2018 | 1-1 v ArbroathRaith Rovers 1-1 Arbroath | Ladbrokes League One |
| 13 | 20/10/2018 | 2-1 v StranraerRaith Rovers 2-1 Stranraer | Ladbrokes League One |
| 14 | 27/10/2018 | 2-3 v Forfar AthleticForfar Athletic 3-2 Raith Rovers | Ladbrokes League One |
| 15 | 3/11/2018 | 2-1 v Brechin CityRaith Rovers 2-1 Brechin City | Ladbrokes League One |
| 16 | 10/11/2018 | 1-2 v East FifeEast Fife 2-1 Raith Rovers | Ladbrokes League One |
| 17 | 17/11/2018 | 3-1 v StenhousemuirStenhousemuir 1-3 Raith Rovers | Ladbrokes League One |
| 18 | 24/11/2018 | 3-0 v Queens ParkQueens Park 0-3 Raith Rovers | William Hill Scottish Cup Third Round |
| 19 | 1/12/2018 | 2-0 v AirdrieoniansRaith Rovers 2-0 Airdrieonians | Ladbrokes League One |
| 20 | 8/12/2018 | 2-3 v MontroseMontrose 3-2 Raith Rovers | Ladbrokes League One |
| 21 | 15/12/2018 | 4-2 v DumbartonRaith Rovers 4-2 Dumbarton | Ladbrokes League One |
| 22 | 22/12/2018 | 2-0 v ArbroathArbroath 0-2 Raith Rovers | Ladbrokes League One |
| 23 | 29/12/2018 | 1-2 v East FifeRaith Rovers 1-2 East Fife | Ladbrokes League One |
| 24 | 5/1/2019 | 5-1 v StenhousemuirRaith Rovers 5-1 Stenhousemuir | Ladbrokes League One |
| 25 | 26/1/2019 | 1-2 v Brechin CityBrechin City 2-1 Raith Rovers | Ladbrokes League One |
| 26 | 2/2/2019 | 1-1 v Forfar AthleticRaith Rovers 1-1 Forfar Athletic | Ladbrokes League One |
| 27 | 9/2/2019 | 1-3 v HibernianHibernian 3-1 Raith Rovers | William Hill Scottish Cup Fifth Round |
| 28 | 16/2/2019 | 0-1 v ArbroathRaith Rovers 0-1 Arbroath | Ladbrokes League One |
| 29 | 23/2/2019 | 4-1 v MontroseRaith Rovers 4-1 Montrose | Ladbrokes League One |
| 30 | 26/2/2019 | 2-2 v DumbartonDumbarton 2-2 Raith Rovers | Ladbrokes League One |
| 31 | 2/3/2019 | 2-2 v StranraerStranraer 2-2 Raith Rovers | Ladbrokes League One |
| 32 | 9/3/2019 | 1-0 v AirdrieoniansRaith Rovers 1-0 Airdrieonians | Ladbrokes League One |
| 33 | 16/3/2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Raith Rovers | Ladbrokes League One |
| 34 | 23/3/2019 | 4-1 v DumbartonRaith Rovers 4-1 Dumbarton | Ladbrokes League One |
| 35 | 6/4/2019 | 1-1 v StenhousemuirStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 36 | 13/4/2019 | 2-3 v StranraerRaith Rovers 2-3 Stranraer | Ladbrokes League One |
| 37 | 21/4/2019 | 2-2 v ArbroathArbroath 2-2 Raith Rovers | Ladbrokes League One |
| 38 | 27/4/2019 | 3-2 v Brechin CityRaith Rovers 3-2 Brechin City | Ladbrokes League One |
| 39 | 7/5/2019 | 2-1 v Forfar AthleticRaith Rovers 2-1 Forfar Athletic | Ladbrokes League One Play-off |
| 40 | 11/5/2019 | 1-1 v Forfar AthleticForfar Athletic 1-1 Raith Rovers | Ladbrokes League One Play-off |
