| 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 | Tue 24 Jul 2018 | 1-2 v Inverness Caledonian ThistleInverness Caledonian Thistle 2-1 Raith Rovers | Betfred Cup Group C |
| 4 | Sat 28 Jul 2018 | 0-2 v Cove RangersCove Rangers 2-0 Raith Rovers | Betfred Cup Group C |
| 5 | Sat 4 Aug 2018 | 1-1 v StranraerStranraer 1-1 Raith Rovers | Ladbrokes League One |
| 6 | Sat 11 Aug 2018 | 2-0 v StenhousemuirRaith Rovers 2-0 Stenhousemuir | Ladbrokes League One |
| 7 | Sat 25 Aug 2018 | 4-3 v AirdrieoniansAirdrieonians 3-4 Raith Rovers | Ladbrokes League One |
| 8 | Sat 1 Sep 2018 | 4-0 v Forfar AthleticRaith Rovers 4-0 Forfar Athletic | Ladbrokes League One |
| 9 | Sat 8 Sep 2018 | 0-5 v Ross CountyRoss County 5-0 Raith Rovers | IRN-BRU Cup Second Round |
| 10 | Sat 15 Sep 2018 | 1-1 v Brechin CityBrechin City 1-1 Raith Rovers | Ladbrokes League One |
| 11 | Sat 20 Oct 2018 | 2-1 v StranraerRaith Rovers 2-1 Stranraer | Ladbrokes League One |
| 12 | Sat 27 Oct 2018 | 2-3 v Forfar AthleticForfar Athletic 3-2 Raith Rovers | Ladbrokes League One |
| 13 | Sat 10 Nov 2018 | 1-2 v East FifeEast Fife 2-1 Raith Rovers | Ladbrokes League One |
| 14 | Sat 17 Nov 2018 | 3-1 v StenhousemuirStenhousemuir 1-3 Raith Rovers | Ladbrokes League One |
| 15 | Sat 4 May 2019 | 1-1 v MontroseMontrose 1-1 Raith Rovers | Ladbrokes League One |
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