| 1 | Sat 17 Aug 2019 | 104-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 102-0 v TilburyGreat Wakering Rovers 2-0 Tilbury | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 100-2 v WalthamstowWalthamstow 2-0 Great Wakering Rovers | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 15 0-2 v Coggeshall TownCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | Sat 31 Aug 2019 | 101-2 v Dereham TownGreat Wakering Rovers 1-2 Dereham Town | BetVictor Isthmian North Division |
| 6 | Sat 14 Sep 2019 | 104-1 v RomfordRomford 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 7 | Tue 17 Sep 2019 | 10 1-1 v Basildon UnitedBasildon United 1-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 8 | Sat 21 Sep 2019 | 102-0 v Witham TownGreat Wakering Rovers 2-0 Witham Town | BetVictor Isthmian North Division |
| 9 | Sat 5 Oct 2019 | 101-4 v HistonHiston 4-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 10 | Sat 12 Oct 2019 | 103-5 v WestfieldGreat Wakering Rovers 3-5 Westfield | Buildbase FA Trophy Preliminary Round |
| 11 | Sat 19 Oct 2019 | 103-1 v Grays AthleticGreat Wakering Rovers 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 12 | Sat 26 Oct 2019 | 102-2 v Brentwood TownBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 13 | Wed 30 Oct 2019 | 83-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 14 | Sat 2 Nov 2019 | 100-2 v Bury TownGreat Wakering Rovers 0-2 Bury Town | BetVictor Isthmian North Division |
| 15 | Sat 9 Nov 2019 | 10 1-0 v Soham Town RangersSoham Town Rangers 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 16 | Tue 12 Nov 2019 | 161-2 v TilburyTilbury 2-1 Great Wakering Rovers | Velocity Trophy Group 6 |
| 17 | Sat 30 Nov 2019 | 102-4 v Heybridge SwiftsHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 18 | Tue 3 Dec 2019 | 100-6 v Concord RangersConcord Rangers 6-0 Great Wakering Rovers | Essex County Cup Fourth Round |
| 19 | Sat 7 Dec 2019 | 80-1 v AveleyGreat Wakering Rovers 0-1 Aveley | BetVictor Isthmian North Division |
| 20 | Sat 14 Dec 2019 | 104-2 v Cambridge CityCambridge City 2-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 21 | Thu 26 Dec 2019 | 104-1 v Hullbridge SportsHullbridge Sports 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 22 | Sat 28 Dec 2019 | 100-0 v Coggeshall TownGreat Wakering Rovers 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 23 | Sat 4 Jan 2020 | 10 4-1 v Dereham TownDereham Town 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 24 | Sat 11 Jan 2020 | 100-1 v Maldon & TiptreeGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 25 | Sat 18 Jan 2020 | 100-1 v Grays AthleticGrays Athletic 1-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 26 | Sat 25 Jan 2020 | 101-3 v HistonGreat Wakering Rovers 1-3 Histon | BetVictor Isthmian North Division |
| 27 | Sat 1 Feb 2020 | 101-0 v Witham TownWitham Town 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 28 | Tue 11 Feb 2020 | 10 0-1 v Basildon UnitedGreat Wakering Rovers 0-1 Basildon United | BetVictor Isthmian North Division |
| 29 | Sat 15 Feb 2020 | 100-4 v Cambridge CityGreat Wakering Rovers 0-4 Cambridge City | BetVictor Isthmian North Division |
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