| 1 | Sat 16 Nov 2019 | 111-1 v Canvey IslandGreat Wakering Rovers 1-1 Canvey Island | BetVictor Isthmian North Division |
| 2 | Sat 30 Nov 2019 | 112-4 v Heybridge SwiftsHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 3 | Tue 3 Dec 2019 | 120-6 v Concord RangersConcord Rangers 6-0 Great Wakering Rovers | Essex County Cup Fourth Round |
| 4 | Sat 7 Dec 2019 | 100-1 v AveleyGreat Wakering Rovers 0-1 Aveley | BetVictor Isthmian North Division |
| 5 | Sat 14 Dec 2019 | 114-2 v Cambridge CityCambridge City 2-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 6 | Thu 26 Dec 2019 | 114-1 v Hullbridge SportsHullbridge Sports 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 7 | Sat 28 Dec 2019 | 110-0 v Coggeshall TownGreat Wakering Rovers 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 8 | Sat 4 Jan 2020 | 114-1 v Dereham TownDereham Town 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 9 | Sat 11 Jan 2020 | 150-1 v Maldon & TiptreeGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 10 | Sat 18 Jan 2020 | 110-1 v Grays AthleticGrays Athletic 1-0 Great Wakering Rovers | BetVictor Isthmian North Division |
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