| 1 | Sat 31 Aug 2019 | 31-2 v Dereham TownGreat Wakering Rovers 1-2 Dereham Town | BetVictor Isthmian North Division |
| 2 | Tue 10 Sep 2019 | 33-0 v Witham TownWitham Town 0-3 Great Wakering Rovers | Velocity Trophy Group 6 |
| 3 | Sat 14 Sep 2019 | 3 4-1 v RomfordRomford 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 4 | Tue 17 Sep 2019 | 31-1 v Basildon UnitedBasildon United 1-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | Tue 24 Sep 2019 | 30-4 v Basildon UnitedGreat Wakering Rovers 0-4 Basildon United | Velocity Trophy Group 6 |
| 6 | Sat 5 Oct 2019 | 3 1-4 v HistonHiston 4-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 7 | Sat 12 Oct 2019 | 33-5 v WestfieldGreat Wakering Rovers 3-5 Westfield | Buildbase FA Trophy Preliminary Round |
| 8 | Tue 22 Oct 2019 | 32-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | Velocity Trophy Group 6 |
| 9 | Wed 30 Oct 2019 | 33-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 10 | Sat 9 Nov 2019 | 31-0 v Soham Town RangersSoham Town Rangers 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 11 | Tue 12 Nov 2019 | 3 1-2 v TilburyTilbury 2-1 Great Wakering Rovers | Velocity Trophy Group 6 |
| 12 | Sat 16 Nov 2019 | 31-1 v Canvey IslandGreat Wakering Rovers 1-1 Canvey Island | BetVictor Isthmian North Division |
| 13 | Tue 26 Nov 2019 | 31-0 v Hullbridge SportsGreat Wakering Rovers 1-0 Hullbridge Sports | Velocity Trophy Group 6 |
| 14 | Sat 30 Nov 2019 | 32-4 v Heybridge SwiftsHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 15 | Tue 3 Dec 2019 | 30-6 v Concord RangersConcord Rangers 6-0 Great Wakering Rovers | Essex County Cup Fourth Round |
| 16 | Sat 7 Dec 2019 | 3 0-1 v AveleyGreat Wakering Rovers 0-1 Aveley | BetVictor Isthmian North Division |
| 17 | Sat 14 Dec 2019 | 164-2 v Cambridge CityCambridge City 2-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 18 | Thu 26 Dec 2019 | 34-1 v Hullbridge SportsHullbridge Sports 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 19 | Sat 28 Dec 2019 | 3 0-0 v Coggeshall TownGreat Wakering Rovers 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 20 | Sat 4 Jan 2020 | 34-1 v Dereham TownDereham Town 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 21 | Sat 11 Jan 2020 | 30-1 v Maldon & TiptreeGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 22 | Sat 18 Jan 2020 | 30-1 v Grays AthleticGrays Athletic 1-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 23 | Sat 25 Jan 2020 | 31-3 v HistonGreat Wakering Rovers 1-3 Histon | BetVictor Isthmian North Division |
| 24 | Sat 1 Feb 2020 | 31-0 v Witham TownWitham Town 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 25 | Tue 11 Feb 2020 | 30-1 v Basildon UnitedGreat Wakering Rovers 0-1 Basildon United | BetVictor Isthmian North Division |
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