| 1 | 10/8/2019 | 16 1-1 v PeterheadEast Fife 1-1 Peterhead | Ladbrokes League One |
| 2 | 18/8/2019 | 160-3 v RangersEast Fife 0-3 Rangers | Betfred Cup Second Round |
| 3 | 24/8/2019 | 164-1 v AirdrieoniansEast Fife 4-1 Airdrieonians | Ladbrokes League One |
| 4 | 31/8/2019 | 16 4-2 v Raith RoversEast Fife 4-2 Raith Rovers | Ladbrokes League One |
| 5 | 7/9/2019 | 162-1 v Forfar AthleticForfar Athletic 1-2 East Fife | Ladbrokes League One |
| 6 | 14/9/2019 | 163-1 v MontroseMontrose 1-3 East Fife | Ladbrokes League One |
| 7 | 21/9/2019 | 162-2 v DumbartonEast Fife 2-2 Dumbarton | Ladbrokes League One |
| 8 | 28/9/2019 | 160-0 v FalkirkFalkirk 0-0 East Fife | Ladbrokes League One |
| 9 | 5/10/2019 | 161-1 v StranraerEast Fife 1-1 Stranraer | Ladbrokes League One |
| 10 | 19/10/2019 | 16 1-0 v Forfar AthleticEast Fife 1-0 Forfar Athletic | Ladbrokes League One |
| 11 | 26/10/2019 | 161-1 v Raith RoversRaith Rovers 1-1 East Fife | Ladbrokes League One |
| 12 | 2/11/2019 | 16 0-1 v MontroseEast Fife 0-1 Montrose | Ladbrokes League One |
| 13 | 9/11/2019 | 164-2 v DumbartonDumbarton 2-4 East Fife | Ladbrokes League One |
| 14 | 26/11/2019 | 160-0 v ClydeEast Fife 0-0 Clyde | Ladbrokes League One |
| 15 | 30/11/2019 | 160-4 v AirdrieoniansAirdrieonians 4-0 East Fife | Ladbrokes League One |
| 16 | 7/12/2019 | 160-0 v FalkirkEast Fife 0-0 Falkirk | Ladbrokes League One |
