| 1 | Sat 10 Aug 2019 | 5-2 v ClydeRaith Rovers 5-2 Clyde | Ladbrokes League One |
| 2 | Sat 17 Aug 2019 | 2-3 v StranraerStranraer 3-2 Raith Rovers | Ladbrokes League One |
| 3 | Sat 24 Aug 2019 | 3-0 v MontroseRaith Rovers 3-0 Montrose | Ladbrokes League One |
| 4 | Sat 31 Aug 2019 | 2-4 v East FifeEast Fife 4-2 Raith Rovers | Ladbrokes League One |
| 5 | Sat 28 Sep 2019 | 2-1 v Forfar AthleticForfar Athletic 1-2 Raith Rovers | Ladbrokes League One |
| 6 | Sat 5 Oct 2019 | 2-2 v FalkirkRaith Rovers 2-2 Falkirk | Ladbrokes League One |
| 7 | Sat 19 Oct 2019 | 2-2 v ClydeClyde 2-2 Raith Rovers | Ladbrokes League One |
| 8 | Sat 14 Dec 2019 | 1-1 v FalkirkFalkirk 1-1 Raith Rovers | Ladbrokes League One |
| 9 | Sat 21 Dec 2019 | 0-2 v DumbartonRaith Rovers 0-2 Dumbarton | Ladbrokes League One |
| 10 | Sat 28 Dec 2019 | 5-3 v East FifeEast Fife 3-5 Raith Rovers | Ladbrokes League One |
| 11 | Sat 4 Jan 2020 | 2-1 v PeterheadRaith Rovers 2-1 Peterhead | Ladbrokes League One |
| 12 | Sat 11 Jan 2020 | 1-1 v Forfar AthleticForfar Athletic 1-1 Raith Rovers | Ladbrokes League One |
| 13 | Sat 18 Jan 2020 | 1-3 v LivingstonLivingston 3-1 Raith Rovers | William Hill Scottish Cup Fourth Round |
| 14 | Sat 25 Jan 2020 | 4-3 v MontroseRaith Rovers 4-3 Montrose | Ladbrokes League One |
| 15 | Sat 8 Feb 2020 | 1-1 v StranraerStranraer 1-1 Raith Rovers | Ladbrokes League One |
| 16 | Fri 14 Feb 2020 | 2-1 v Partick ThistlePartick Thistle 1-2 Raith Rovers | Tunnock's Challenge Cup Semi Final |
| 17 | Sat 22 Feb 2020 | 1-0 v ClydeRaith Rovers 1-0 Clyde | Ladbrokes League One |
| 18 | Sat 29 Feb 2020 | 0-1 v DumbartonDumbarton 1-0 Raith Rovers | Ladbrokes League One |
| 19 | Tue 3 Mar 2020 | 1-1 v FalkirkRaith Rovers 1-1 Falkirk | Ladbrokes League One |
| 20 | Sat 7 Mar 2020 | 2-1 v Forfar AthleticRaith Rovers 2-1 Forfar Athletic | Ladbrokes League One |
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