| 1 | Sat 17 Aug 2019 | 4 4-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 42-0 v TilburyGreat Wakering Rovers 2-0 Tilbury | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 4 0-2 v WalthamstowWalthamstow 2-0 Great Wakering Rovers | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 40-2 v Coggeshall TownCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | Sat 31 Aug 2019 | 41-2 v Dereham TownGreat Wakering Rovers 1-2 Dereham Town | BetVictor Isthmian North Division |
| 6 | Tue 10 Sep 2019 | 43-0 v Witham TownWitham Town 0-3 Great Wakering Rovers | Velocity Trophy Group 6 |
| 7 | Sat 14 Sep 2019 | 44-1 v RomfordRomford 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 8 | Tue 17 Sep 2019 | 4 1-1 v Basildon UnitedBasildon United 1-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 9 | Sat 21 Sep 2019 | 42-0 v Witham TownGreat Wakering Rovers 2-0 Witham Town | BetVictor Isthmian North Division |
| 10 | Sat 5 Oct 2019 | 4 1-4 v HistonHiston 4-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 11 | Sat 19 Oct 2019 | 43-1 v Grays AthleticGreat Wakering Rovers 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 12 | Sat 26 Oct 2019 | 42-2 v Brentwood TownBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 13 | Wed 30 Oct 2019 | 193-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 14 | Sat 2 Nov 2019 | 4 0-2 v Bury TownGreat Wakering Rovers 0-2 Bury Town | BetVictor Isthmian North Division |
| 15 | Tue 12 Nov 2019 | 41-2 v TilburyTilbury 2-1 Great Wakering Rovers | Velocity Trophy Group 6 |
| 16 | Sat 16 Nov 2019 | 41-1 v Canvey IslandGreat Wakering Rovers 1-1 Canvey Island | BetVictor Isthmian North Division |
| 17 | Tue 26 Nov 2019 | 4 1-0 v Hullbridge SportsGreat Wakering Rovers 1-0 Hullbridge Sports | Velocity Trophy Group 6 |
| 18 | Sat 30 Nov 2019 | 4 2-4 v Heybridge SwiftsHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 19 | Tue 3 Dec 2019 | 40-6 v Concord RangersConcord Rangers 6-0 Great Wakering Rovers | Essex County Cup Fourth Round |
| 20 | Sat 14 Dec 2019 | 4 4-2 v Cambridge CityCambridge City 2-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 21 | Thu 26 Dec 2019 | 4 4-1 v Hullbridge SportsHullbridge Sports 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
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