| 1 | Sat 31 Aug 2019 | 2-4 v East FifeEast Fife 4-2 Raith Rovers | Ladbrokes League One |
| 2 | Sat 28 Sep 2019 | 2-1 v Forfar AthleticForfar Athletic 1-2 Raith Rovers | Ladbrokes League One |
| 3 | Sat 5 Oct 2019 | 2-2 v FalkirkRaith Rovers 2-2 Falkirk | Ladbrokes League One |
| 4 | Sat 19 Oct 2019 | 2-2 v ClydeClyde 2-2 Raith Rovers | Ladbrokes League One |
| 5 | Sat 26 Oct 2019 | 1-1 v East FifeRaith Rovers 1-1 East Fife | Ladbrokes League One |
| 6 | Sat 2 Nov 2019 | 0-2 v PeterheadPeterhead 2-0 Raith Rovers | Ladbrokes League One |
| 7 | Sat 9 Nov 2019 | 3-1 v StranraerRaith Rovers 3-1 Stranraer | Ladbrokes League One |
| 8 | Tue 26 Nov 2019 | 0-0 v Forfar AthleticRaith Rovers 0-0 Forfar Athletic | Ladbrokes League One |
| 9 | Sat 30 Nov 2019 | 1-0 v MontroseMontrose 0-1 Raith Rovers | Ladbrokes League One |
| 10 | Sat 7 Dec 2019 | 1-0 v AirdrieoniansRaith Rovers 1-0 Airdrieonians | Ladbrokes League One |
| 11 | Sat 14 Dec 2019 | 1-1 v FalkirkFalkirk 1-1 Raith Rovers | Ladbrokes League One |
| 12 | Sat 21 Dec 2019 | 0-2 v DumbartonRaith Rovers 0-2 Dumbarton | Ladbrokes League One |
| 13 | Sat 28 Dec 2019 | 5-3 v East FifeEast Fife 3-5 Raith Rovers | Ladbrokes League One |
| 14 | Sat 4 Jan 2020 | 2-1 v PeterheadRaith Rovers 2-1 Peterhead | Ladbrokes League One |
| 15 | Sat 11 Jan 2020 | 1-1 v Forfar AthleticForfar Athletic 1-1 Raith Rovers | Ladbrokes League One |
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