| 1 | 17/8/2019 | 84-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | 20/8/2019 | 82-0 v TilburyGreat Wakering Rovers 2-0 Tilbury | BetVictor Isthmian North Division |
| 3 | 24/8/2019 | 80-2 v WalthamstowWalthamstow 2-0 Great Wakering Rovers | Emirates FA Cup Preliminary Round |
| 4 | 26/8/2019 | 80-2 v Coggeshall TownCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | 31/8/2019 | 81-2 v Dereham TownGreat Wakering Rovers 1-2 Dereham Town | BetVictor Isthmian North Division |
| 6 | 10/9/2019 | 83-0 v Witham TownWitham Town 0-3 Great Wakering Rovers | Velocity Trophy Group 6 |
| 7 | 14/9/2019 | 84-1 v RomfordRomford 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 8 | 17/9/2019 | 8 1-1 v Basildon UnitedBasildon United 1-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 9 | 21/9/2019 | 82-0 v Witham TownGreat Wakering Rovers 2-0 Witham Town | BetVictor Isthmian North Division |
| 10 | 5/10/2019 | 81-4 v HistonHiston 4-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 11 | 19/10/2019 | 173-1 v Grays AthleticGreat Wakering Rovers 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 12 | 22/10/2019 | 82-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | Velocity Trophy Group 6 |
| 13 | 26/10/2019 | 152-2 v Brentwood TownBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 14 | 30/10/2019 | 163-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 15 | 2/11/2019 | 160-2 v Bury TownGreat Wakering Rovers 0-2 Bury Town | BetVictor Isthmian North Division |
| 16 | 9/11/2019 | 4 1-0 v Soham Town RangersSoham Town Rangers 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 17 | 12/11/2019 | 101-2 v TilburyTilbury 2-1 Great Wakering Rovers | Velocity Trophy Group 6 |
| 18 | 16/11/2019 | 81-1 v Canvey IslandGreat Wakering Rovers 1-1 Canvey Island | BetVictor Isthmian North Division |
| 19 | 26/11/2019 | 8 1-0 v Hullbridge SportsGreat Wakering Rovers 1-0 Hullbridge Sports | Velocity Trophy Group 6 |
| 20 | 30/11/2019 | 82-4 v Heybridge SwiftsHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 21 | 3/12/2019 | 160-6 v Concord RangersConcord Rangers 6-0 Great Wakering Rovers | Essex County Cup Fourth Round |
| 22 | 7/12/2019 | 4 0-1 v AveleyGreat Wakering Rovers 0-1 Aveley | BetVictor Isthmian North Division |
| 23 | 14/12/2019 | 84-2 v Cambridge CityCambridge City 2-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 24 | 26/12/2019 | 84-1 v Hullbridge SportsHullbridge Sports 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 25 | 28/12/2019 | 80-0 v Coggeshall TownGreat Wakering Rovers 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 26 | 4/1/2020 | 84-1 v Dereham TownDereham Town 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 27 | 11/1/2020 | 110-1 v Maldon & TiptreeGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 28 | 18/1/2020 | 4 0-1 v Grays AthleticGrays Athletic 1-0 Great Wakering Rovers | BetVictor Isthmian North Division |
