| 1 | Sat 17 Aug 2019 | 2 4-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-4 Great Wakering Rovers | BetVictor Isthmian North Division |
| 2 | Sat 31 Aug 2019 | 21-2 v Dereham TownGreat Wakering Rovers 1-2 Dereham Town | BetVictor Isthmian North Division |
| 3 | Tue 10 Sep 2019 | 23-0 v Witham TownWitham Town 0-3 Great Wakering Rovers | Velocity Trophy Group 6 |
| 4 | Tue 24 Sep 2019 | 20-4 v Basildon UnitedGreat Wakering Rovers 0-4 Basildon United | Velocity Trophy Group 6 |
| 5 | Sat 5 Oct 2019 | 21-4 v HistonHiston 4-1 Great Wakering Rovers | BetVictor Isthmian North Division |
| 6 | Sat 12 Oct 2019 | 23-5 v WestfieldGreat Wakering Rovers 3-5 Westfield | Buildbase FA Trophy Preliminary Round |
| 7 | Sat 19 Oct 2019 | 23-2 v Cambridge CityCambridge City 2-3 Brentwood Town | BetVictor Isthmian North Division |
| 8 | Sat 26 Oct 2019 | 2 2-2 v Great Wakering RoversBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 9 | Sat 2 Nov 2019 | 23-3 v Felixstowe & Walton UnitedFelixstowe & Walton United 3-3 Brentwood Town | BetVictor Isthmian North Division |
| 10 | Tue 5 Nov 2019 | 22-4 v HornchurchBrentwood Town 2-4 Hornchurch | Essex County Cup Third Round |
| 11 | Tue 12 Nov 2019 | 22-3 v Canvey IslandCanvey Island 3-2 Brentwood Town | BetVictor Isthmian North Division |
| 12 | Sat 16 Nov 2019 | 2 2-5 v Dereham TownDereham Town 5-2 Brentwood Town | BetVictor Isthmian North Division |
| 13 | Sat 30 Nov 2019 | 22-3 v Basildon UnitedBasildon United 3-2 Brentwood Town | BetVictor Isthmian North Division |
| 14 | Sat 7 Dec 2019 | 72-1 v Soham Town RangersBrentwood Town 2-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 15 | Tue 10 Dec 2019 | 73-4 v Hullbridge SportsBrentwood Town 3-4 Hullbridge Sports | BetVictor Isthmian North Division |
| 16 | Sat 4 Jan 2020 | 71-0 v Coggeshall TownCoggeshall Town 0-1 Brentwood Town | BetVictor Isthmian North Division |
| 17 | Tue 7 Jan 2020 | 73-0 v Witham TownWitham Town 0-3 Brentwood Town | BetVictor Isthmian North Division |
| 18 | Sat 11 Jan 2020 | 71-1 v HistonBrentwood Town 1-1 Histon | BetVictor Isthmian North Division |
| 19 | Tue 21 Jan 2020 | 70-1 v Heybridge SwiftsBrentwood Town 0-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 20 | Sat 25 Jan 2020 | 120-1 v AFC SudburyAFC Sudbury 1-0 Brentwood Town | BetVictor Isthmian North Division |
| 21 | Sat 8 Feb 2020 | 21-2 v Soham Town RangersSoham Town Rangers 2-1 Brentwood Town | BetVictor Isthmian North Division |
| 22 | Tue 11 Feb 2020 | 2 2-3 v RomfordRomford 3-2 Brentwood Town | BetVictor Isthmian North Division |
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