| 1 | Sat 17 Aug 2019 | 124-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 122-0 v TilburyGreat Wakering Rovers 2-0 Tilbury | BetVictor Isthmian North Division |
| 3 | Sat 31 Aug 2019 | 121-2 v Dereham TownGreat Wakering Rovers 1-2 Dereham Town | BetVictor Isthmian North Division |
| 4 | Tue 10 Sep 2019 | 103-0 v Witham TownWitham Town 0-3 Great Wakering Rovers | Velocity Trophy Group 6 |
| 5 | Sat 14 Sep 2019 | 124-1 v RomfordRomford 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 6 | Sat 21 Sep 2019 | 162-0 v Witham TownGreat Wakering Rovers 2-0 Witham Town | BetVictor Isthmian North Division |
| 7 | Tue 24 Sep 2019 | 70-4 v Basildon UnitedGreat Wakering Rovers 0-4 Basildon United | Velocity Trophy Group 6 |
| 8 | Sat 5 Oct 2019 | 141-4 v HistonHiston 4-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 9 | Sat 12 Oct 2019 | 73-5 v WestfieldGreat Wakering Rovers 3-5 Westfield | Buildbase FA Trophy Preliminary Round |
| 10 | Sat 19 Oct 2019 | 163-1 v Grays AthleticGreat Wakering Rovers 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 11 | Tue 22 Oct 2019 | 7 2-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | Velocity Trophy Group 6 |
| 12 | Sat 26 Oct 2019 | 16 2-2 v Brentwood TownBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 13 | Wed 30 Oct 2019 | 7 3-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 14 | Sat 2 Nov 2019 | 7 0-2 v Bury TownGreat Wakering Rovers 0-2 Bury Town | BetVictor Isthmian North Division |
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