| Date | Competition | Opponent | Venue | Result | East Fife Scorers | Att. | Referee |
| 25 Jun 19 | Friendly | Albion Rovers | Locality Hub Bayview Stadium | 1-0 W | Hunter | ||
| 29 Jun 19 | Friendly | Dundee United | Locality Hub Bayview Stadium | 1-1 D | OG | ||
| 02 Jul 19 | Friendly | Queen of the South | Locality Hub Bayview Stadium | 1-2 L | Dowds | ||
| 06 Jul 19 | Friendly | Kirrie Thistle | Westview Park | 1-4 W | Denholm (2), Hunter, Watt | ||
| 13 Jul 19 | Betfred Cup Group A | Cowdenbeath | Central Park | 2-0 L | 469 | David Dickinson | |
| 20 Jul 19 | Betfred Cup Group A | Stenhousemuir | Locality Hub Bayview Stadium | 2-0 W | Agnew (2) | 308 | Duncan Williams |
| 23 Jul 19 | Betfred Cup Group A | Dundee United | Tannadice Park | 2-0 W | Dunsmore, Watt | 2778 | Graham Beaton |
| 27 Jul 19 | Betfred Cup Group A | Heart of Midlothian | Locality Hub Bayview Stadium |
1-1 D EF win 7-6 on pens |
Duggan | 1998 | David Munro |
| 03 Aug 19 | Ladbrokes League 1 | Clyde | Broadwood Stadium | 1-1 D | Dowds | 836 | Barry Cook |
| 10 Aug 19 | Ladbrokes League 1 | Peterhead | Locality Hub Bayview Stadium | 1-1 D | Wallace | 570 | Lloyd Wilson |
| 13 Aug 19 | Tunnock’s Caramel Wafer Cup R2 | Stirling Albion | Locality Hub Bayview Stadium | 0-2 L | 419 | Grant Irvine | |
| 18 Aug 19 | Betfred Cup R2 | Rangers | Locality Hub Bayview Stadium | 0-3 L | 1991 | Don Robertson | |
| 24 Aug 19 | Ladbrokes League 1 | Airdrieonians | Lacality Hub Bayview Stadium | 4-1 W | Davidson, Watt, Dunsmore, Agnew | 620 | Graham Beaton |
| 31 Aug 19 | Ladbrokes League 1 | Raith Rovers | Locality Hub Bayview Stadium | 4-2 W | Dowds, Higgins, Wallace, Agnew | 1792 | Craig Napier |
| 07 Sep 19 | Ladbrokes League 1 | Forfar Athletic | Station Park | 1-2 W | Agenw, Dowds | 619 | Kevin Graham |
| 14 Sep 19 | Ladbrokes League 1 | Montrose | Links Park | 3-1 W | Dunsmore (2), Wallace | 561 | Greg Aitken |
| 21 Sep 19 | Ladbrokes League 1 | Dumbarton | Locality Hub Bayview Stadium | 2-2 D | Murdoch, Agnew (P) | 719 | Lloyd Wilson |
| 28 Sep 19 | Ladbrokes League 1 | Falkirk | The Falkirk Stadium | 0-0 D | 3993 | David Dickinson | |
| 05 Oct 19 | Ladbrokes League 1 | Stranraer | Locality Hub Bayview Stadium | 1-1 D | Wallace | 526 | Kevin Graham |
| 19 Oct 19 | Ladbrokes League 1 | Forfar Athletic | Locality Hub Bayview Stadium | 1-0 W | Boyd | 667 | Duncan Williams |
| 26 Oct 19 | Ladbrokes League 1 | Raith Rovers | Stark’s Park | 1-1 D | Boyd | 2907 | Barry Cook |
| 02 Nov 19 | Ladbrokes League 1 | Montrose | Locality Hub Bayview Stadium | 0-1 L | 704 | David Lowe | |
| 09 Nov 19 | Ladbrokes League 1 | Dumbarton | C&G Systems Stadium | 2-4W | Denholm, Watt (2), Boyd | 702 | Chris Graham |
| 23 Nov 19 | William Hill Scottish Cup R3 | BSC Glasgow | Locality Hub Bayview Stadium | 3-4 L | Dowds, Watt, Watson | 484 | Matthew MacDermid |
| 26 Nov 19 | Ladbrokes League 1 | Clyde | Locality Hub Bayview Stadium | 0-0 D | 426 | Barry Cook | |
| 30 Nov 19 | Ladbrokes League 1 | Airdrieonians | The Penny Cars Stadium | 4-0 L | 910 | Gavin Ross | |
| 07 Dec 19 | Ladbrokes League 1 | Falkirk | Locality Hub Bayview Stadium | 0-0 D | 1182 | Crzig Napier | |
| 14 Dec 19 | Ladbrokes League 1 | Stranraer | Stair Park | 0-2 W | Davidson, Agnew | 274 | Duncan Williams |
| 21 Dec 19 | Ladbrokes League 1 | Peterhead | Balmoor Stadium | 1-2 W | Denholm, Agnew | 599 | Kevin Graham |
| 28 Dec 19 | Ladbrokes League 1 | Raith Rovers | Locality Hub Bayview Stadium | 3-5 L | Agnew, Dowds, Wallace | 1998 | Don Robertson |
| 04 Jan 20 | Ladbrokes League 1 | Montrose | Links Park | 1-0 L | 833 | Chris Graham | |
| 11 Jan 20 | Ladbrokes League 1 | Airdrieonains | Locality Hub Bayview Stadium | 2-2 D | Dunsmore, Watson | 783 | David Lowe |
| 18 Jan 20 | Friendly | Civil Service Strollers | Locality Hub Bayview Stadium | 1-0 W | Denholm | ||
| 25 Jan 20 | Ladbrokes League 1 | Clyde | Broadwood Stadium | 2-1 L | Dunsmore | 954 | Alan Newlands |
| 01 Feb 20 | Ladbrokes League 1 | Dumbarton | Locality Hub Bayview Stadium | 4-2 W | OG, Higgins, Murdoch, Agnew | 536 | Gavin Duncan |
| 15 Feb 20 | Ladbrokes League 1 | Peterhead | Locality Hub Bayview Stadium | ||||
| 18 Feb 20 | Ladbrokes League 1 | Falkirk | The Falkirk Stadium | ||||
| 22 Feb 20 | Ladbrokes League 1 | Stranraer | Locality Hub Bayview Stadium | ||||
| 29 Feb 20 | Ladbrokes League 1 | Forfar Athletic | Station Park | ||||
| 07 Mar 20 | Ladbrokes League 1 | Airdrieonians | The Penny Cars Stadium | ||||
| 14 Mar 20 | Ladbrokes League 1 | Montrose | Locality Hub Bayview Stadium | ||||
| 21 Mar 20 | Ladbrokes League 1 | Raith Rovers | Stark’s Park | ||||
| 28 Mar 20 | Ladbrokes League 1 | Clyde | Locality Hub Bayview Stadium | ||||
| 04 Apr 20 | Ladbrokes League 1 | Stranraer | Stair Park | ||||
| 11 Apr 20 | Ladbrokes League 1 | Forfar Athletic | Locality Hub Bayview Stadium | ||||
| 18 Apr 20 | Ladbrokes League 1 | Dumbarton | C&G Systems Stadium | ||||
| 25 Apr 20 | Ladbrokes League 1 | Falkirk | Locality Hub Bayview Stadium | ||||
| 02 May 20 | Ladbrokes League 1 | Peterhead | Balmoor Stadium | ||||
| 05 May 20 | Ladbrokes Play-Off SF Leg 1 | ||||||
| 09 May 20 | Ladbrokes Play-Off SF Leg 2 | ||||||
| 12 May 20 | Ladbrokes Play-Off F Leg 1 | ||||||
| 16 May 20 | Ladbrokes Play-Off F Leg 2 |
