| 1 | Sat 17 Aug 2019 | 6 1-4 v Grays AthleticGrays Athletic 4-1 Brentwood Town | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 31-2 v Maldon & TiptreeBrentwood Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 3 | Tue 3 Sep 2019 | 32-1 v Harlow TownBrentwood Town 2-1 Harlow Town | Emirates FA Cup Preliminary Round |
| 4 | Sat 7 Sep 2019 | 31-2 v Bowers & PitseaBowers & Pitsea 2-1 Brentwood Town | Emirates FA Cup First Qualifying Round |
| 5 | Tue 17 Sep 2019 | 31-3 v AveleyBrentwood Town 1-3 Aveley | BetVictor Isthmian North Division |
| 6 | Tue 24 Sep 2019 | 33-2 v AveleyBrentwood Town 3-2 Aveley | Velocity Trophy Group 2 |
| 7 | Fri 27 Sep 2019 | 60-2 v BarkingBarking 2-0 Brentwood Town | Velocity Trophy Group 2 |
| 8 | Sat 5 Oct 2019 | 63-1 v AFC SudburyBrentwood Town 3-1 AFC Sudbury | BetVictor Isthmian North Division |
| 9 | Tue 8 Oct 2019 | 61-3 v RomfordRomford 3-1 Brentwood Town | Velocity Trophy Group 2 |
| 10 | Sat 12 Oct 2019 | 32-3 v Basildon UnitedBrentwood Town 2-3 Basildon United | Buildbase FA Trophy Preliminary Round |
| 11 | Tue 15 Oct 2019 | 122-1 v Waltham AbbeyWaltham Abbey 1-2 Brentwood Town | Velocity Trophy Group 2 |
| 12 | Sat 19 Oct 2019 | 33-2 v Cambridge CityCambridge City 2-3 Brentwood Town | BetVictor Isthmian North Division |
| 13 | Sat 26 Oct 2019 | 3 2-2 v Great Wakering RoversBrentwood Town 2-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 14 | Sat 2 Nov 2019 | 33-3 v Felixstowe & Walton UnitedFelixstowe & Walton United 3-3 Brentwood Town | BetVictor Isthmian North Division |
| 15 | Tue 5 Nov 2019 | 32-4 v HornchurchBrentwood Town 2-4 Hornchurch | Essex County Cup Third Round |
| 16 | Tue 12 Nov 2019 | 62-3 v Canvey IslandCanvey Island 3-2 Brentwood Town | BetVictor Isthmian North Division |
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