| 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 | 17/11/2018 | 3-1 v StenhousemuirStenhousemuir 1-3 Raith Rovers | Ladbrokes League One |
| 11 | 2/3/2019 | 2-2 v StranraerStranraer 2-2 Raith Rovers | Ladbrokes League One |
| 12 | 9/3/2019 | 1-0 v AirdrieoniansRaith Rovers 1-0 Airdrieonians | Ladbrokes League One |
| 13 | 16/3/2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Raith Rovers | Ladbrokes League One |
| 14 | 23/3/2019 | 4-1 v DumbartonRaith Rovers 4-1 Dumbarton | Ladbrokes League One |
| 15 | 6/4/2019 | 1-1 v StenhousemuirStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 16 | 13/4/2019 | 2-3 v StranraerRaith Rovers 2-3 Stranraer | Ladbrokes League One |
| 17 | 21/4/2019 | 2-2 v ArbroathArbroath 2-2 Raith Rovers | Ladbrokes League One |
| 18 | 27/4/2019 | 3-2 v Brechin CityRaith Rovers 3-2 Brechin City | Ladbrokes League One |
| 19 | 4/5/2019 | 1-1 v MontroseMontrose 1-1 Raith Rovers | Ladbrokes League One |
| 20 | 7/5/2019 | 2-1 v Forfar AthleticRaith Rovers 2-1 Forfar Athletic | Ladbrokes League One Play-off |
| 21 | 11/5/2019 | 1-1 v Forfar AthleticForfar Athletic 1-1 Raith Rovers | Ladbrokes League One Play-off |
