| 1 | Tue 13 Aug 2019 | 60-2 v Stirling AlbionEast Fife 0-2 Stirling Albion | Tunnock's Challenge Cup Second Round |
| 2 | Sat 31 Aug 2019 | 64-2 v Raith RoversEast Fife 4-2 Raith Rovers | Ladbrokes League One |
| 3 | Sat 7 Sep 2019 | 62-1 v Forfar AthleticForfar Athletic 1-2 East Fife | Ladbrokes League One |
| 4 | Sat 5 Oct 2019 | 61-1 v StranraerEast Fife 1-1 Stranraer | Ladbrokes League One |
| 5 | Sat 19 Oct 2019 | 61-0 v Forfar AthleticEast Fife 1-0 Forfar Athletic | Ladbrokes League One |
| 6 | Sat 2 Nov 2019 | 60-1 v MontroseEast Fife 0-1 Montrose | Ladbrokes League One |
| 7 | Sat 9 Nov 2019 | 64-2 v DumbartonDumbarton 2-4 East Fife | Ladbrokes League One |
| 8 | Tue 26 Nov 2019 | 60-0 v ClydeEast Fife 0-0 Clyde | Ladbrokes League One |
| 9 | Sat 30 Nov 2019 | 60-4 v AirdrieoniansAirdrieonians 4-0 East Fife | Ladbrokes League One |
| 10 | Sat 7 Dec 2019 | 60-0 v FalkirkEast Fife 0-0 Falkirk | Ladbrokes League One |
| 11 | Sat 14 Dec 2019 | 62-0 v StranraerStranraer 0-2 East Fife | Ladbrokes League One |
| 12 | Sat 21 Dec 2019 | 62-1 v PeterheadPeterhead 1-2 East Fife | Ladbrokes League One |
| 13 | Sat 28 Dec 2019 | 63-5 v Raith RoversEast Fife 3-5 Raith Rovers | Ladbrokes League One |
| 14 | Sat 4 Jan 2020 | 60-1 v MontroseMontrose 1-0 East Fife | Ladbrokes League One |
| 15 | Sat 11 Jan 2020 | 62-2 v AirdrieoniansEast Fife 2-2 Airdrieonians | Ladbrokes League One |
| 16 | Sat 25 Jan 2020 | 61-2 v ClydeClyde 2-1 East Fife | Ladbrokes League One |
| 17 | Sat 1 Feb 2020 | 64-2 v DumbartonEast Fife 4-2 Dumbarton | Ladbrokes League One |
| 18 | Sat 22 Feb 2020 | 64-2 v StranraerEast Fife 4-2 Stranraer | Ladbrokes League One |
| 19 | Sat 29 Feb 2020 | 61-0 v Forfar AthleticForfar Athletic 0-1 East Fife | Ladbrokes League One |
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