| 1 | 24/7/2018 | 1-2 v Inverness Caledonian ThistleInverness Caledonian Thistle 2-1 Raith Rovers | Betfred Cup Group C |
| 2 | 28/7/2018 | 0-2 v Cove RangersCove Rangers 2-0 Raith Rovers | Betfred Cup Group C |
| 3 | 4/8/2018 | 1-1 v StranraerStranraer 1-1 Raith Rovers | Ladbrokes League One |
| 4 | 11/8/2018 | 2-0 v StenhousemuirRaith Rovers 2-0 Stenhousemuir | Ladbrokes League One |
| 5 | 15/9/2018 | 1-1 v Brechin CityBrechin City 1-1 Raith Rovers | Ladbrokes League One |
| 6 | 22/9/2018 | 1-1 v MontroseRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 7 | 6/10/2018 | 1-1 v ArbroathRaith Rovers 1-1 Arbroath | Ladbrokes League One |
| 8 | 27/10/2018 | 2-3 v Forfar AthleticForfar Athletic 3-2 Raith Rovers | Ladbrokes League One |
| 9 | 3/11/2018 | 2-1 v Brechin CityRaith Rovers 2-1 Brechin City | Ladbrokes League One |
| 10 | 17/11/2018 | 3-1 v StenhousemuirStenhousemuir 1-3 Raith Rovers | Ladbrokes League One |
| 11 | 1/12/2018 | 2-0 v AirdrieoniansRaith Rovers 2-0 Airdrieonians | Ladbrokes League One |
| 12 | 22/12/2018 | 2-0 v ArbroathArbroath 0-2 Raith Rovers | Ladbrokes League One |
| 13 | 29/12/2018 | 1-2 v East FifeRaith Rovers 1-2 East Fife | Ladbrokes League One |
| 14 | 5/1/2019 | 5-1 v StenhousemuirRaith Rovers 5-1 Stenhousemuir | Ladbrokes League One |
| 15 | 12/1/2019 | 1-1 v AirdrieoniansAirdrieonians 1-1 Raith Rovers | Ladbrokes League One |
