| 1 | Tue 10 Sep 2019 | 163-0 v Witham TownWitham Town 0-3 Great Wakering Rovers | Velocity Trophy Group 6 |
| 2 | Tue 17 Sep 2019 | 161-1 v Basildon UnitedBasildon United 1-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 3 | Sat 21 Sep 2019 | 152-0 v Witham TownGreat Wakering Rovers 2-0 Witham Town | BetVictor Isthmian North Division |
| 4 | Tue 24 Sep 2019 | 40-4 v Basildon UnitedGreat Wakering Rovers 0-4 Basildon United | Velocity Trophy Group 6 |
| 5 | Sat 12 Oct 2019 | 43-5 v WestfieldGreat Wakering Rovers 3-5 Westfield | Buildbase FA Trophy Preliminary Round |
| 6 | Tue 22 Oct 2019 | 42-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | Velocity Trophy Group 6 |
| 7 | Wed 30 Oct 2019 | 153-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 8 | Sat 9 Nov 2019 | 151-0 v Soham Town RangersSoham Town Rangers 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 9 | Tue 12 Nov 2019 | 8 1-2 v TilburyTilbury 2-1 Great Wakering Rovers | Velocity Trophy Group 6 |
| 10 | Sat 16 Nov 2019 | 141-1 v Canvey IslandGreat Wakering Rovers 1-1 Canvey Island | BetVictor Isthmian North Division |
| 11 | Tue 26 Nov 2019 | 161-0 v Hullbridge SportsGreat Wakering Rovers 1-0 Hullbridge Sports | Velocity Trophy Group 6 |
| 12 | Sat 14 Dec 2019 | 124-2 v Cambridge CityCambridge City 2-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 13 | Sat 4 Jan 2020 | 164-1 v Dereham TownDereham Town 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 14 | Sat 25 Jan 2020 | 21-3 v HistonGreat Wakering Rovers 1-3 Histon | BetVictor Isthmian North Division |
| 15 | Sat 1 Feb 2020 | 41-0 v Witham TownWitham Town 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 16 | Tue 11 Feb 2020 | 110-1 v Basildon UnitedGreat Wakering Rovers 0-1 Basildon United | BetVictor Isthmian North Division |
| 17 | Sat 15 Feb 2020 | 40-4 v Cambridge CityGreat Wakering Rovers 0-4 Cambridge City | BetVictor Isthmian North Division |
| 18 | Tue 18 Feb 2020 | 22-0 v AFC SudburyGreat Wakering Rovers 2-0 AFC Sudbury | BetVictor Isthmian North Division |
| 19 | Sat 22 Feb 2020 | 103-0 v Bury TownBury Town 0-3 Great Wakering Rovers | BetVictor Isthmian North Division |
| 20 | Sat 7 Mar 2020 | 22-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | BetVictor Isthmian North Division |
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