| 1 | Sat 5 Aug 2023 | 2 2-0 v Shefford Town & CamptonShefford Town & Campton 0-2 Maldon & Tiptree | Emirates FA Cup Extra Preliminary Round |
| 2 | Sat 12 Aug 2023 | 22-2 v Felixstowe & Walton UnitedMaldon & Tiptree 2-2 Felixstowe & Walton United | Isthmian League - North Division |
| 3 | Sat 19 Aug 2023 | 20-0 v West EssexMaldon & Tiptree 0-0 West Essex | Emirates FA Cup Preliminary Round |
| 4 | Tue 22 Aug 2023 | 23-0 v West EssexWest Essex 0-3 Maldon & Tiptree | Emirates FA Cup Preliminary Round Replay |
| 5 | Sat 26 Aug 2023 | 20-2 v Lowestoft TownLowestoft Town 2-0 Maldon & Tiptree | Isthmian League - North Division |
| 6 | Mon 28 Aug 2023 | 21-1 v Grays AthleticMaldon & Tiptree 1-1 Grays Athletic | Isthmian League - North Division |
| 7 | Sun 3 Sep 2023 | 20-8 v BiggleswadeBiggleswade 8-0 Maldon & Tiptree | Emirates FA Cup First Qualifying Round |
| 8 | Tue 12 Sep 2023 | 21-2 v Bowers & PitseaBowers & Pitsea 2-1 Maldon & Tiptree | Velocity Cup First Round |
| 9 | Sat 16 Sep 2023 | 20-1 v WalthamstowWalthamstow 1-0 Maldon & Tiptree | Isthmian League - North Division |
| 10 | Sat 30 Sep 2023 | 20-3 v Brightlingsea RegentBrightlingsea Regent 3-0 Maldon & Tiptree | Isthmian League - North Division |
| 11 | Sat 7 Oct 2023 | 23-2 v EnfieldMaldon & Tiptree 3-2 Enfield | Isthmian League - North Division |
| 12 | Tue 10 Oct 2023 | 2 3-2 v Basildon UnitedMaldon & Tiptree 3-2 Basildon United | Isthmian League - North Division |
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