| 1 | Sat 5 Jul | 10-5 v Leyton OrientBrentwood Town 0-5 Leyton Orient | Friendly |
| 2 | Tue 8 Jul | 10-0 v Chelmsford CityBrentwood Town 0-0 Chelmsford City | Friendly |
| 3 | Sat 12 Jul | 10-2 v HornchurchBrentwood Town 0-2 Hornchurch | Friendly |
| 4 | Sat 19 Jul | 15-0 v Grays AthleticBrentwood Town 5-0 Grays Athletic | Friendly |
| 5 | Tue 29 Jul | 16-1 v Brightlingsea RegentBrentwood Town 6-1 Brightlingsea Regent | Friendly |
| 6 | Fri 1 Aug | 12-0 v TilburyBrentwood Town 2-0 Tilbury | Friendly |
| 7 | Fri 8 Aug | 11-1 v AveleyAveley 1-1 Brentwood Town | Isthmian League - Premier Division |
| 8 | Tue 12 Aug | 13-2 v St Albans CityBrentwood Town 3-2 St Albans City | Isthmian League - Premier Division |
| 9 | Sat 16 Aug | 14-3 v Potters Bar TownPotters Bar Town 3-4 Brentwood Town | Isthmian League - Premier Division |
| 10 | Sat 23 Aug | 12-1 v Burgess Hill TownBrentwood Town 2-1 Burgess Hill Town | Isthmian League - Premier Division |
| 11 | Mon 25 Aug | 15-1 v Cray WanderersCray Wanderers 1-5 Brentwood Town | Isthmian League - Premier Division |
| 12 | Sat 30 Aug | 12-1 v Leighton TownBrentwood Town 2-1 Leighton Town | Emirates FA Cup First Qualifying Round |
| 13 | Sat 6 Sep | 13-2 v Carshalton AthleticBrentwood Town 3-2 Carshalton Athletic | Isthmian League - Premier Division |
| 14 | Tue 9 Sep | 11-0 v Canvey IslandBrentwood Town 1-0 Canvey Island | Isthmian League - Premier Division |
| 15 | Sat 13 Sep | 10-1 v Royston TownRoyston Town 1-0 Brentwood Town | Emirates FA Cup Second Qualifying Round |
| 16 | Sat 20 Sep | 13-0 v Billericay TownBrentwood Town 3-0 Billericay Town | Isthmian League - Premier Division |
| 17 | Sat 27 Sep | 12-1 v Dulwich HamletDulwich Hamlet 1-2 Brentwood Town | Isthmian League - Premier Division |
| 18 | Sat 4 Oct | 12-1 v WestfieldWestfield 1-2 Brentwood Town | Isuzu FA Trophy Third Qualifying Round |
| 19 | Sat 11 Oct | 11-1 v DartfordBrentwood Town 1-1 Dartford | Isthmian League - Premier Division |
| 20 | Tue 14 Oct | 12-3 v Canvey IslandCanvey Island 3-2 Brentwood Town | Isthmian League - Premier Division |
| 21 | Sat 18 Oct | 12-1 v RamsgateBrentwood Town 2-1 Ramsgate | Isthmian League - Premier Division |
| 22 | Sat 25 Oct | 13-0 v Welling UnitedBrentwood Town 3-0 Welling United | Isuzu FA Trophy First Round |
| 23 | Tue 28 Oct | 13-1 v Cray Valley PMCray Valley PM 1-3 Brentwood Town | Isthmian League - Premier Division |
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