| 1 | Sat 17 Aug 2019 | 11-4 v Grays AthleticGrays Athletic 4-1 Brentwood Town |
| 2 | Tue 20 Aug 2019 | 11-2 v Maldon & TiptreeBrentwood Town 1-2 Maldon & Tiptree |
| 3 | Mon 26 Aug 2019 | 10-1 v TilburyTilbury 1-0 Brentwood Town |
| 4 | Sat 31 Aug 2019 | 10-1 v Coggeshall TownBrentwood Town 0-1 Coggeshall Town |
| 5 | Sat 14 Sep 2019 | 11-1 v Bury TownBury Town 1-1 Brentwood Town |
| 6 | Tue 17 Sep 2019 | 11-3 v AveleyBrentwood Town 1-3 Aveley |
| 7 | Sat 5 Oct 2019 | 13-1 v AFC SudburyBrentwood Town 3-1 AFC Sudbury |
| 8 | Sat 19 Oct 2019 | 1 3-2 v Cambridge CityCambridge City 2-3 Brentwood Town |
| 9 | Sat 26 Oct 2019 | 12-2 v Great Wakering RoversBrentwood Town 2-2 Great Wakering Rovers |
| 10 | Sat 2 Nov 2019 | 13-3 v Felixstowe & Walton UnitedFelixstowe & Walton United 3-3 Brentwood Town |
| 11 | Tue 12 Nov 2019 | 12-3 v Canvey IslandCanvey Island 3-2 Brentwood Town |
| 12 | Sat 16 Nov 2019 | 12-5 v Dereham TownDereham Town 5-2 Brentwood Town |
| 13 | Sat 30 Nov 2019 | 12-3 v Basildon UnitedBasildon United 3-2 Brentwood Town |
| 14 | Sat 7 Dec 2019 | 12-1 v Soham Town RangersBrentwood Town 2-1 Soham Town Rangers |
| 15 | Tue 10 Dec 2019 | 13-4 v Hullbridge SportsBrentwood Town 3-4 Hullbridge Sports |
| 16 | Sat 4 Jan 2020 | 11-0 v Coggeshall TownCoggeshall Town 0-1 Brentwood Town |
| 17 | Tue 7 Jan 2020 | 13-0 v Witham TownWitham Town 0-3 Brentwood Town |
| 18 | Sat 11 Jan 2020 | 11-1 v HistonBrentwood Town 1-1 Histon |
| 19 | Tue 21 Jan 2020 | 10-1 v Heybridge SwiftsBrentwood Town 0-1 Heybridge Swifts |
| 20 | Sat 25 Jan 2020 | 10-1 v AFC SudburyAFC Sudbury 1-0 Brentwood Town |
| 21 | Sat 8 Feb 2020 | 11-2 v Soham Town RangersSoham Town Rangers 2-1 Brentwood Town |
| 22 | Tue 11 Feb 2020 | 12-3 v RomfordRomford 3-2 Brentwood Town |
| 23 | Sat 15 Feb 2020 | 12-0 v Witham TownBrentwood Town 2-0 Witham Town |
| 24 | Mon 17 Feb 2020 | 14-3 v TilburyBrentwood Town 4-3 Tilbury |
| 25 | Sat 22 Feb 2020 | 10-2 v Felixstowe & Walton UnitedBrentwood Town 0-2 Felixstowe & Walton United |
| 26 | Tue 25 Feb 2020 | 10-2 v Cambridge CityBrentwood Town 0-2 Cambridge City |
| 27 | Mon 2 Mar 2020 | 10-0 v AveleyAveley 0-0 Brentwood Town |
| 28 | Sat 7 Mar 2020 | 11-3 v Dereham TownBrentwood Town 1-3 Dereham Town |
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