| 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 | Sat 4 Aug 2018 | 0-2 v DumbartonEast Fife 0-2 Dumbarton | Ladbrokes League One |
| 4 | Tue 14 Aug 2018 | 3-1 v CowdenbeathCowdenbeath 1-3 East Fife | IRN-BRU Cup First Round |
| 5 | Sat 25 Aug 2018 | 0-3 v ArbroathEast Fife 0-3 Arbroath | Ladbrokes League One |
| 6 | Sat 27 Oct 2018 | 70-4 v DumbartonDumbarton 4-0 East Fife | Ladbrokes League One |
| 7 | Sat 3 Nov 2018 | 70-1 v ArbroathArbroath 1-0 East Fife | Ladbrokes League One |
| 8 | Sat 12 Jan 2019 | 72-0 v MontroseMontrose 0-2 East Fife | Ladbrokes League One |
| 9 | Sat 26 Jan 2019 | 2-1 v Raith RoversBrechin City 2-1 Raith Rovers | Ladbrokes League One |
| 10 | Sat 2 Feb 2019 | 2-5 v MontroseMontrose 5-2 Brechin City | Ladbrokes League One |
| 11 | Sat 23 Feb 2019 | 1-2 v StranraerBrechin City 1-2 Stranraer | Ladbrokes League One |
| 12 | Tue 5 Mar 2019 | 0-0 v East FifeBrechin City 0-0 East Fife | Ladbrokes League One |
| 13 | Sat 9 Mar 2019 | 2-2 v Forfar AthleticBrechin City 2-2 Forfar Athletic | Ladbrokes League One |
| 14 | Tue 26 Mar 2019 | 2-0 v StranraerStranraer 0-2 Brechin City | Ladbrokes League One |
| 15 | Sat 30 Mar 2019 | 0-3 v AirdrieoniansBrechin City 0-3 Airdrieonians | Ladbrokes League One |
| 16 | Tue 2 Apr 2019 | 0-3 v MontroseBrechin City 0-3 Montrose | Ladbrokes League One |
| 17 | Sat 6 Apr 2019 | 1-2 v DumbartonDumbarton 2-1 Brechin City | Ladbrokes League One |
| 18 | Sat 13 Apr 2019 | 1-1 v ArbroathBrechin City 1-1 Arbroath | Ladbrokes League One |
| 19 | Sat 4 May 2019 | 1-1 v StenhousemuirBrechin City 1-1 Stenhousemuir | Ladbrokes League One |
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