| 1 | 20/8/2019 | 111-2 v Maldon & TiptreeBrentwood Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 2 | 24/8/2019 | 111-1 v Harlow TownHarlow Town 1-1 Brentwood Town | Emirates FA Cup Preliminary Round |
| 3 | 26/8/2019 | 11 0-1 v TilburyTilbury 1-0 Brentwood Town | BetVictor Isthmian North Division |
| 4 | 3/9/2019 | 11 2-1 v Harlow TownBrentwood Town 2-1 Harlow Town | Emirates FA Cup Preliminary Round |
| 5 | 7/9/2019 | 111-2 v Bowers & PitseaBowers & Pitsea 2-1 Brentwood Town | Emirates FA Cup First Qualifying Round |
| 6 | 14/9/2019 | 111-1 v Bury TownBury Town 1-1 Brentwood Town | BetVictor Isthmian North Division |
| 7 | 17/9/2019 | 111-3 v AveleyBrentwood Town 1-3 Aveley | BetVictor Isthmian North Division |
| 8 | 24/9/2019 | 43-2 v AveleyBrentwood Town 3-2 Aveley | Velocity Trophy Group 2 |
| 9 | 27/9/2019 | 100-2 v BarkingBarking 2-0 Brentwood Town | Velocity Trophy Group 2 |
| 10 | 5/10/2019 | 113-1 v AFC SudburyBrentwood Town 3-1 AFC Sudbury | BetVictor Isthmian North Division |
| 11 | 8/10/2019 | 111-3 v RomfordRomford 3-1 Brentwood Town | Velocity Trophy Group 2 |
| 12 | 12/10/2019 | 112-3 v Basildon UnitedBrentwood Town 2-3 Basildon United | Buildbase FA Trophy Preliminary Round |
| 13 | 15/10/2019 | 11 2-1 v Waltham AbbeyWaltham Abbey 1-2 Brentwood Town | Velocity Trophy Group 2 |
| 14 | 19/10/2019 | 113-2 v Cambridge CityCambridge City 2-3 Brentwood Town | BetVictor Isthmian North Division |
| 15 | 26/10/2019 | 72-2 v Great Wakering RoversBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 16 | 2/11/2019 | 11 3-3 v Felixstowe & Walton UnitedFelixstowe & Walton United 3-3 Brentwood Town | BetVictor Isthmian North Division |
| 17 | 5/11/2019 | 82-4 v HornchurchBrentwood Town 2-4 Hornchurch | Essex County Cup Third Round |
| 18 | 12/11/2019 | 92-3 v Canvey IslandCanvey Island 3-2 Brentwood Town | BetVictor Isthmian North Division |
| 19 | 16/11/2019 | 92-5 v Dereham TownDereham Town 5-2 Brentwood Town | BetVictor Isthmian North Division |
| 20 | 30/11/2019 | 92-3 v Basildon UnitedBasildon United 3-2 Brentwood Town | BetVictor Isthmian North Division |
| 21 | 2/12/2019 | 43-1 v Grays AthleticBrentwood Town 3-1 Grays Athletic | Velocity Trophy Group 2 |
| 22 | 7/12/2019 | 42-1 v Soham Town RangersBrentwood Town 2-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 23 | 10/12/2019 | 43-4 v Hullbridge SportsBrentwood Town 3-4 Hullbridge Sports | BetVictor Isthmian North Division |
| 24 | 4/1/2020 | 4 1-0 v Coggeshall TownCoggeshall Town 0-1 Brentwood Town | BetVictor Isthmian North Division |
| 25 | 7/1/2020 | 43-0 v Witham TownWitham Town 0-3 Brentwood Town | BetVictor Isthmian North Division |
| 26 | 11/1/2020 | 41-1 v HistonBrentwood Town 1-1 Histon | BetVictor Isthmian North Division |
| 27 | 21/1/2020 | 40-1 v Heybridge SwiftsBrentwood Town 0-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 28 | 25/1/2020 | 40-1 v AFC SudburyAFC Sudbury 1-0 Brentwood Town | BetVictor Isthmian North Division |
