| 1 | Sat 8 Aug | 62-0 v Burgess Hill TownBrentwood Town 2-0 Burgess Hill Town | Isthmian League - Premier Division |
| 2 | Tue 11 Aug | 60-1 v DartfordDartford 1-0 Brentwood Town | Isthmian League - Premier Division |
| 3 | Sat 15 Aug | 62-3 v Eastbourne BoroughEastbourne Borough 3-2 Brentwood Town | Isthmian League - Premier Division |
| 4 | Sat 22 Aug | 61-3 v Enfield TownBrentwood Town 1-3 Enfield Town | Isthmian League - Premier Division |
| 5 | Sat 29 Aug | 6 0-2 v Carshalton AthleticCarshalton Athletic 2-0 Brentwood Town | Isthmian League - Premier Division |
| 6 | Tue 8 Sep | 64-2 v Concord RangersBrentwood Town 4-2 Concord Rangers | Emirates FA Cup First Qualifying Round Replay |
| 7 | Sat 12 Sep | 61-2 v Dulwich HamletDulwich Hamlet 2-1 Brentwood Town | Isthmian League - Premier Division |
| 8 | Tue 15 Sep | 62-3 v Stanway RoversBrentwood Town 2-3 Stanway Rovers | Isthmian League - Premier Division |
| 9 | Sat 19 Sep | 63-2 v AveleyAveley 2-3 Brentwood Town | Emirates FA Cup Second Qualifying Round |
| 10 | Tue 22 Sep | 65-1 v Maldon & TiptreeBrentwood Town 5-1 Maldon & Tiptree | Isthmian League - Premier Division |
| 11 | Sat 26 Sep | 63-3 v Hashtag UnitedBrentwood Town 3-3 Hashtag United | FA Trophy Third Qualifying Round |
| 12 | Wed 30 Sep | 62-1 v AFC WhyteleafeAFC Whyteleafe 1-2 Brentwood Town | Isthmian League - Premier Division |
| 13 | Sat 3 Oct | 63-1 v Dagenham & RedbridgeBrentwood Town 3-1 Dagenham & Redbridge | Emirates FA Cup Third Qualifying Round |
| 14 | Sat 10 Oct | 60-3 v Chatham TownChatham Town 3-0 Brentwood Town | Isthmian League - Premier Division |
| 15 | Sat 17 Oct | 62-3 v EastleighEastleigh 3-2 Brentwood Town | Emirates FA Cup Fourth Qualifying Round |
| 16 | Tue 20 Oct | 63-0 v DartfordBrentwood Town 3-0 Dartford | Isthmian League - Premier Division |
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