| 1 | Sat 10 Aug 2019 | 1-1 v PeterheadEast Fife 1-1 Peterhead | Ladbrokes League One |
| 2 | Sun 18 Aug 2019 | 0-3 v RangersEast Fife 0-3 Rangers | Betfred Cup Second Round |
| 3 | Sat 24 Aug 2019 | 4-1 v AirdrieoniansEast Fife 4-1 Airdrieonians | Ladbrokes League One |
| 4 | Sat 31 Aug 2019 | 4-2 v Raith RoversEast Fife 4-2 Raith Rovers | Ladbrokes League One |
| 5 | Sat 7 Sep 2019 | 2-1 v Forfar AthleticForfar Athletic 1-2 East Fife | Ladbrokes League One |
| 6 | Sat 14 Sep 2019 | 3-1 v MontroseMontrose 1-3 East Fife | Ladbrokes League One |
| 7 | Sat 21 Sep 2019 | 2-2 v DumbartonEast Fife 2-2 Dumbarton | Ladbrokes League One |
| 8 | Sat 5 Oct 2019 | 1-1 v StranraerEast Fife 1-1 Stranraer | Ladbrokes League One |
| 9 | Sat 19 Oct 2019 | 1-0 v Forfar AthleticEast Fife 1-0 Forfar Athletic | Ladbrokes League One |
| 10 | Sat 7 Dec 2019 | 0-0 v FalkirkEast Fife 0-0 Falkirk | Ladbrokes League One |
| 11 | Sat 14 Dec 2019 | 2-0 v StranraerStranraer 0-2 East Fife | Ladbrokes League One |
| 12 | Sat 21 Dec 2019 | 2-1 v PeterheadPeterhead 1-2 East Fife | Ladbrokes League One |
| 13 | Sat 28 Dec 2019 | 3-5 v Raith RoversEast Fife 3-5 Raith Rovers | Ladbrokes League One |
| 14 | Sat 4 Jan 2020 | 0-1 v MontroseMontrose 1-0 East Fife | Ladbrokes League One |
| 15 | Sat 11 Jan 2020 | 2-2 v AirdrieoniansEast Fife 2-2 Airdrieonians | Ladbrokes League One |
| 16 | Sat 25 Jan 2020 | 1-2 v ClydeClyde 2-1 East Fife | Ladbrokes League One |
| 17 | Sat 1 Feb 2020 | 4-2 v DumbartonEast Fife 4-2 Dumbarton | Ladbrokes League One |
| 18 | Sat 15 Feb 2020 | 1-0 v PeterheadEast Fife 1-0 Peterhead | Ladbrokes League One |
| 19 | Tue 18 Feb 2020 | 0-2 v FalkirkFalkirk 2-0 East Fife | Ladbrokes League One |
| 20 | Sat 22 Feb 2020 | 4-2 v StranraerEast Fife 4-2 Stranraer | Ladbrokes League One |
| 21 | Sat 29 Feb 2020 | 1-0 v Forfar AthleticForfar Athletic 0-1 East Fife | Ladbrokes League One |
| 22 | Sat 7 Mar 2020 | 0-1 v AirdrieoniansAirdrieonians 1-0 East Fife | Ladbrokes League One |
Football Web Pages