| 1 | Sat 14 Jul 2018 | 0-0 v St JohnstoneSt Johnstone 0-0 East Fife | Betfred Cup Group B |
| 2 | Tue 17 Jul 2018 | 0-1 v MontroseMontrose 1-0 East Fife | Betfred Cup Group B |
| 3 | Sun 22 Jul 2018 | 1-1 v Forfar AthleticEast Fife 1-1 Forfar Athletic | Betfred Cup Group B |
| 4 | Sat 28 Jul 2018 | 1-2 v FalkirkEast Fife 1-2 Falkirk | Betfred Cup Group B |
| 5 | Sat 4 Aug 2018 | 0-2 v DumbartonEast Fife 0-2 Dumbarton | Ladbrokes League One |
| 6 | Sat 11 Aug 2018 | 0-1 v Brechin CityBrechin City 1-0 East Fife | Ladbrokes League One |
| 7 | Sat 25 Aug 2018 | 0-3 v ArbroathEast Fife 0-3 Arbroath | Ladbrokes League One |
| 8 | Sat 1 Sep 2018 | 2-0 v MontroseMontrose 0-2 East Fife | Ladbrokes League One |
| 9 | Sat 15 Sep 2018 | 2-1 v AirdrieoniansEast Fife 2-1 Airdrieonians | Ladbrokes League One |
| 10 | Sat 6 Oct 2018 | 4-0 v Forfar AthleticForfar Athletic 0-4 East Fife | Ladbrokes League One |
| 11 | Sat 13 Oct 2018 | 2-0 v Queen of the SouthEast Fife 2-0 Queen of the South | IRN-BRU Cup Third Round |
| 12 | Sat 20 Oct 2018 | 3-1 v Brechin CityEast Fife 3-1 Brechin City | Ladbrokes League One |
| 13 | Sat 27 Oct 2018 | 0-4 v DumbartonDumbarton 4-0 East Fife | Ladbrokes League One |
| 14 | Sat 3 Nov 2018 | 0-1 v ArbroathArbroath 1-0 East Fife | Ladbrokes League One |
| 15 | Sat 10 Nov 2018 | 2-1 v Raith RoversEast Fife 2-1 Raith Rovers | Ladbrokes League One |
| 16 | Sat 17 Nov 2018 | 2-4 v AirdrieoniansAirdrieonians 4-2 East Fife | Ladbrokes League One |
| 17 | Sat 24 Nov 2018 | 2-1 v Berwick RangersBerwick Rangers 1-2 East Fife | William Hill Scottish Cup Third Round |
| 18 | Sat 1 Dec 2018 | 0-2 v MontroseEast Fife 0-2 Montrose | Ladbrokes League One |
| 19 | Sat 8 Dec 2018 | 3-3 v StranraerEast Fife 3-3 Stranraer | Ladbrokes League One |
| 20 | Sat 15 Dec 2018 | 2-0 v StenhousemuirStenhousemuir 0-2 East Fife | Ladbrokes League One |
| 21 | Sat 22 Dec 2018 | 1-0 v Forfar AthleticEast Fife 1-0 Forfar Athletic | Ladbrokes League One |
| 22 | Sat 29 Dec 2018 | 2-1 v Raith RoversRaith Rovers 1-2 East Fife | Ladbrokes League One |
| 23 | Sat 5 Jan 2019 | 1-2 v AirdrieoniansEast Fife 1-2 Airdrieonians | Ladbrokes League One |
| 24 | Sat 12 Jan 2019 | 2-0 v MontroseMontrose 0-2 East Fife | Ladbrokes League One |
| 25 | Sat 19 Jan 2019 | 2-1 v Greenock MortonEast Fife 2-1 Greenock Morton | William Hill Scottish Cup Fourth Round |
| 26 | Sat 26 Jan 2019 | 4-3 v StranraerStranraer 3-4 East Fife | Ladbrokes League One |
| 27 | Sat 9 Feb 2019 | 0-1 v Partick ThistleEast Fife 0-1 Partick Thistle | William Hill Scottish Cup Fifth Round |
| 28 | Fri 15 Feb 2019 | 1-2 v Ross CountyRoss County 2-1 East Fife | IRN-BRU Cup Quarter Final |
| 29 | Sat 2 Mar 2019 | 0-3 v Forfar AthleticForfar Athletic 3-0 East Fife | Ladbrokes League One |
| 30 | Tue 5 Mar 2019 | 0-0 v Brechin CityBrechin City 0-0 East Fife | Ladbrokes League One |
| 31 | Sat 9 Mar 2019 | 3-1 v StranraerEast Fife 3-1 Stranraer | Ladbrokes League One |
| 32 | Tue 12 Mar 2019 | 1-1 v StenhousemuirEast Fife 1-1 Stenhousemuir | Ladbrokes League One |
| 33 | Sat 16 Mar 2019 | 1-2 v ArbroathArbroath 2-1 East Fife | Ladbrokes League One |
| 34 | Sat 23 Mar 2019 | 0-2 v Brechin CityEast Fife 0-2 Brechin City | Ladbrokes League One |
| 35 | Sat 30 Mar 2019 | 1-2 v Raith RoversEast Fife 1-2 Raith Rovers | Ladbrokes League One |
| 36 | Sat 6 Apr 2019 | 0-0 v AirdrieoniansAirdrieonians 0-0 East Fife | Ladbrokes League One |
| 37 | Sat 20 Apr 2019 | 0-3 v DumbartonDumbarton 3-0 East Fife | Ladbrokes League One |
| 38 | Sat 27 Apr 2019 | 1-1 v StenhousemuirStenhousemuir 1-1 East Fife | Ladbrokes League One |
| 39 | Sat 4 May 2019 | 2-3 v Forfar AthleticEast Fife 2-3 Forfar Athletic | Ladbrokes League One |
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