| 1 | Sat 17 Aug 2019 | 54-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 52-0 v TilburyGreat Wakering Rovers 2-0 Tilbury | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 50-2 v WalthamstowWalthamstow 2-0 Great Wakering Rovers | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 30-2 v Coggeshall TownCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | Sat 31 Aug 2019 | 51-2 v Dereham TownGreat Wakering Rovers 1-2 Dereham Town | BetVictor Isthmian North Division |
| 6 | Tue 10 Sep 2019 | 63-0 v Witham TownWitham Town 0-3 Great Wakering Rovers | Velocity Trophy Group 6 |
| 7 | Tue 17 Sep 2019 | 21-1 v Basildon UnitedBasildon United 1-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 8 | Sat 21 Sep 2019 | 6 2-0 v Witham TownGreat Wakering Rovers 2-0 Witham Town | BetVictor Isthmian North Division |
| 9 | Sat 5 Oct 2019 | 51-4 v HistonHiston 4-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 10 | Sat 12 Oct 2019 | 6 3-5 v WestfieldGreat Wakering Rovers 3-5 Westfield | Buildbase FA Trophy Preliminary Round |
| 11 | Tue 22 Oct 2019 | 52-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | Velocity Trophy Group 6 |
| 12 | Sat 26 Oct 2019 | 62-2 v Brentwood TownBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 13 | Wed 30 Oct 2019 | 63-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 14 | Sat 2 Nov 2019 | 60-2 v Bury TownGreat Wakering Rovers 0-2 Bury Town | BetVictor Isthmian North Division |
| 15 | Sat 9 Nov 2019 | 61-0 v Soham Town RangersSoham Town Rangers 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 16 | Sat 16 Nov 2019 | 61-1 v Canvey IslandGreat Wakering Rovers 1-1 Canvey Island | BetVictor Isthmian North Division |
| 17 | Tue 26 Nov 2019 | 181-0 v Hullbridge SportsGreat Wakering Rovers 1-0 Hullbridge Sports | Velocity Trophy Group 6 |
| 18 | Sat 30 Nov 2019 | 62-4 v Heybridge SwiftsHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 19 | Tue 3 Dec 2019 | 50-6 v Concord RangersConcord Rangers 6-0 Great Wakering Rovers | Essex County Cup Fourth Round |
| 20 | Sat 7 Dec 2019 | 50-1 v AveleyGreat Wakering Rovers 0-1 Aveley | BetVictor Isthmian North Division |
| 21 | Sat 14 Dec 2019 | 54-2 v Cambridge CityCambridge City 2-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 22 | Thu 26 Dec 2019 | 64-1 v Hullbridge SportsHullbridge Sports 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 23 | Sat 28 Dec 2019 | 60-0 v Coggeshall TownGreat Wakering Rovers 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 24 | Sat 4 Jan 2020 | 64-1 v Dereham TownDereham Town 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 25 | Sat 11 Jan 2020 | 40-1 v Maldon & TiptreeGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 26 | Sat 18 Jan 2020 | 60-1 v Grays AthleticGrays Athletic 1-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 27 | Sat 25 Jan 2020 | 61-3 v HistonGreat Wakering Rovers 1-3 Histon | BetVictor Isthmian North Division |
| 28 | Sat 1 Feb 2020 | 61-0 v Witham TownWitham Town 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
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