| 1 | Sat 26 Oct 2019 | 92-2 v Brentwood TownBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | Wed 30 Oct 2019 | 93-2 v RomfordRomford 2-3 Great Wakering Rovers | Essex County Cup Third Round |
| 3 | Sat 2 Nov 2019 | 90-2 v Bury TownGreat Wakering Rovers 0-2 Bury Town | BetVictor Isthmian North Division |
| 4 | Sat 9 Nov 2019 | 91-0 v Soham Town RangersSoham Town Rangers 0-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | Sat 16 Nov 2019 | 91-1 v Canvey IslandGreat Wakering Rovers 1-1 Canvey Island | BetVictor Isthmian North Division |
| 6 | Sat 30 Nov 2019 | 92-4 v Heybridge SwiftsHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 7 | Tue 3 Dec 2019 | 90-6 v Concord RangersConcord Rangers 6-0 Great Wakering Rovers | Essex County Cup Fourth Round |
| 8 | Sat 7 Dec 2019 | 160-1 v AveleyGreat Wakering Rovers 0-1 Aveley | BetVictor Isthmian North Division |
| 9 | Sat 28 Dec 2019 | 160-0 v Coggeshall TownGreat Wakering Rovers 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 10 | Sat 4 Jan 2020 | 144-1 v Dereham TownDereham Town 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
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