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