| 1 | Sat 17 Aug 2019 | 6 4-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 62-0 v TilburyGreat Wakering Rovers 2-0 Tilbury | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 6 0-2 v WalthamstowWalthamstow 2-0 Great Wakering Rovers | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 60-2 v Coggeshall TownCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | Sat 31 Aug 2019 | 61-2 v Dereham TownGreat Wakering Rovers 1-2 Dereham Town | BetVictor Isthmian North Division |
| 6 | Sat 14 Sep 2019 | 6 4-1 v RomfordRomford 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 7 | Tue 17 Sep 2019 | 6 1-1 v Basildon UnitedBasildon United 1-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 8 | Sat 19 Oct 2019 | 63-1 v Grays AthleticGreat Wakering Rovers 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 9 | Tue 22 Oct 2019 | 62-0 v Canvey IslandCanvey Island 0-2 Great Wakering Rovers | Velocity Trophy Group 6 |
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