| 1 | 22/7/2018 | 1-1 v Forfar AthleticEast Fife 1-1 Forfar Athletic | Betfred Cup Group B |
| 2 | 11/8/2018 | 0-1 v Brechin CityBrechin City 1-0 East Fife | Ladbrokes League One |
| 3 | 25/8/2018 | 0-3 v ArbroathEast Fife 0-3 Arbroath | Ladbrokes League One |
| 4 | 6/10/2018 | 4-0 v Forfar AthleticForfar Athletic 0-4 East Fife | Ladbrokes League One |
| 5 | 13/10/2018 | 2-0 v Queen of the SouthEast Fife 2-0 Queen of the South | IRN-BRU Cup Third Round |
| 6 | 3/11/2018 | 0-1 v ArbroathArbroath 1-0 East Fife | Ladbrokes League One |
| 7 | 10/11/2018 | 2-1 v Raith RoversEast Fife 2-1 Raith Rovers | Ladbrokes League One |
| 8 | 8/12/2018 | 3-3 v StranraerEast Fife 3-3 Stranraer | Ladbrokes League One |
| 9 | 15/12/2018 | 2-0 v StenhousemuirStenhousemuir 0-2 East Fife | Ladbrokes League One |
| 10 | 22/12/2018 | 1-0 v Forfar AthleticEast Fife 1-0 Forfar Athletic | Ladbrokes League One |
| 11 | 9/2/2019 | 0-1 v Partick ThistleEast Fife 0-1 Partick Thistle | William Hill Scottish Cup Fifth Round |
| 12 | 23/2/2019 | 3-4 v DumbartonEast Fife 3-4 Dumbarton | Ladbrokes League One |
| 13 | 5/3/2019 | 0-0 v Brechin CityBrechin City 0-0 East Fife | Ladbrokes League One |
| 14 | 16/3/2019 | 1-2 v ArbroathArbroath 2-1 East Fife | Ladbrokes League One |
| 15 | 30/3/2019 | 1-2 v Raith RoversEast Fife 1-2 Raith Rovers | Ladbrokes League One |
| 16 | 20/4/2019 | 0-3 v DumbartonDumbarton 3-0 East Fife | Ladbrokes League One |
| 17 | 4/5/2019 | 2-3 v Forfar AthleticEast Fife 2-3 Forfar Athletic | Ladbrokes League One |
