| 1 | Sat 17 Aug 2019 | 144-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 142-0 v TilburyGreat Wakering Rovers 2-0 Tilbury | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 140-2 v WalthamstowWalthamstow 2-0 Great Wakering Rovers | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 110-2 v Coggeshall TownCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | Tue 10 Sep 2019 | 153-0 v Witham TownWitham Town 0-3 Great Wakering Rovers | Velocity Trophy Group 6 |
| 6 | Tue 17 Sep 2019 | 141-1 v Basildon UnitedBasildon United 1-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 7 | Tue 24 Sep 2019 | 110-4 v Basildon UnitedGreat Wakering Rovers 0-4 Basildon United | Velocity Trophy Group 6 |
| 8 | Sat 5 Oct 2019 | 121-4 v HistonHiston 4-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 9 | Sat 12 Oct 2019 | 113-5 v WestfieldGreat Wakering Rovers 3-5 Westfield | Buildbase FA Trophy Preliminary Round |
| 10 | Sat 19 Oct 2019 | 143-1 v Grays AthleticGreat Wakering Rovers 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 11 | Tue 22 Oct 2019 | 112-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | Velocity Trophy Group 6 |
| 12 | Wed 30 Oct 2019 | 143-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 13 | Tue 26 Nov 2019 | 151-0 v Hullbridge SportsGreat Wakering Rovers 1-0 Hullbridge Sports | Velocity Trophy Group 6 |
| 14 | Sat 7 Dec 2019 | 120-1 v AveleyGreat Wakering Rovers 0-1 Aveley | BetVictor Isthmian North Division |
| 15 | Sat 14 Dec 2019 | 34-2 v Cambridge CityCambridge City 2-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 16 | Thu 26 Dec 2019 | 144-1 v Hullbridge SportsHullbridge Sports 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 17 | Sat 28 Dec 2019 | 140-0 v Coggeshall TownGreat Wakering Rovers 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 18 | Sat 4 Jan 2020 | 154-1 v Dereham TownDereham Town 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 19 | Sat 11 Jan 2020 | 170-1 v Maldon & TiptreeGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 20 | Sat 18 Jan 2020 | 140-1 v Grays AthleticGrays Athletic 1-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 21 | Tue 18 Feb 2020 | 112-0 v AFC SudburyGreat Wakering Rovers 2-0 AFC Sudbury | BetVictor Isthmian North Division |
| 22 | Sat 22 Feb 2020 | 113-0 v Bury TownBury Town 0-3 Great Wakering Rovers | BetVictor Isthmian North Division |
| 23 | Sat 7 Mar 2020 | 112-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | BetVictor Isthmian North Division |
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