| 1 | Sat 30 Sep 2023 | 112-3 v Lowestoft TownGrays Athletic 2-3 Lowestoft Town | Isthmian League - North Division |
| 2 | Sat 28 Oct 2023 | 14 0-3 v Felixstowe & Walton UnitedGrays Athletic 0-3 Felixstowe & Walton United | Isthmian League - North Division |
| 3 | Sat 4 Nov 2023 | 111-2 v Brightlingsea RegentBrightlingsea Regent 2-1 Grays Athletic | Isthmian League - North Division |
| 4 | Sat 16 Dec 2023 | 114-0 v EnfieldGrays Athletic 4-0 Enfield | Isthmian League - North Division |
| 5 | Fri 22 Dec 2023 | 110-5 v Concord RangersConcord Rangers 5-0 Grays Athletic | Essex County Cup Fourth Round |
| 6 | Tue 26 Dec 2023 | 171-3 v Bowers & PitseaBowers & Pitsea 3-1 Grays Athletic | Isthmian League - North Division |
| 7 | Mon 1 Jan 2024 | 170-1 v Maldon & TiptreeGrays Athletic 0-1 Maldon & Tiptree | Isthmian League - North Division |
| 8 | Sat 13 Jan 2024 | 73-1 v Maldon & TiptreeMaldon & Tiptree 1-3 Brentwood Town | Isthmian League - North Division |
| 9 | Sat 20 Jan 2024 | 73-1 v RedbridgeRedbridge 1-3 Brentwood Town | Isthmian League - North Division |
| 10 | Sat 27 Jan 2024 | 122-0 v WalthamstowBrentwood Town 2-0 Walthamstow | Isthmian League - North Division |
| 11 | Sat 3 Feb 2024 | 73-2 v GorlestonGorleston 2-3 Brentwood Town | Isthmian League - North Division |
| 12 | Tue 6 Feb 2024 | 150-1 v Lowestoft TownBrentwood Town 0-1 Lowestoft Town | Isthmian League - North Division |
| 13 | Sat 17 Feb 2024 | 72-1 v Heybridge SwiftsHeybridge Swifts 1-2 Brentwood Town | Isthmian League - North Division |
| 14 | Tue 9 Apr 2024 | 171-3 v Bowers & PitseaBrentwood Town 1-3 Bowers & Pitsea | Isthmian League - North Division |
| 15 | Sat 13 Apr 2024 | 121-0 v WroxhamWroxham 0-1 Brentwood Town | Isthmian League - North Division |
| 16 | Tue 16 Apr 2024 | 71-0 v Basildon UnitedBasildon United 0-1 Brentwood Town | Isthmian League - North Division |
| 17 | Sat 20 Apr 2024 | 140-2 v Brightlingsea RegentBrentwood Town 0-2 Brightlingsea Regent | Isthmian League - North Division |
| 18 | Sat 27 Apr 2024 | 142-1 v Lowestoft TownLowestoft Town 1-2 Brentwood Town | Isthmian League - North Division |
| 19 | Sat 4 May 2024 | 151-1 v Bowers & PitseaBowers & Pitsea 1-1 Brentwood Town | Isthmian League - North Division Play-off Final |
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