| 1 | Sat 5 Aug 2023 | 12-0 v Shefford Town & CamptonShefford Town & Campton 0-2 Maldon & Tiptree | Emirates FA Cup Extra Preliminary Round |
| 2 | Sat 12 Aug 2023 | 12-2 v Felixstowe & Walton UnitedMaldon & Tiptree 2-2 Felixstowe & Walton United | Isthmian League - North Division |
| 3 | Sat 19 Aug 2023 | 10-0 v West EssexMaldon & Tiptree 0-0 West Essex | Emirates FA Cup Preliminary Round |
| 4 | Tue 22 Aug 2023 | 13-0 v West EssexWest Essex 0-3 Maldon & Tiptree | Emirates FA Cup Preliminary Round Replay |
| 5 | Sat 26 Aug 2023 | 10-2 v Lowestoft TownLowestoft Town 2-0 Maldon & Tiptree | Isthmian League - North Division |
| 6 | Mon 28 Aug 2023 | 11-1 v Grays AthleticMaldon & Tiptree 1-1 Grays Athletic | Isthmian League - North Division |
| 7 | Sun 3 Sep 2023 | 10-8 v BiggleswadeBiggleswade 8-0 Maldon & Tiptree | Emirates FA Cup First Qualifying Round |
| 8 | Sat 9 Sep 2023 | 10-3 v Witham TownWitham Town 3-0 Maldon & Tiptree | Isuzu FA Trophy First Qualifying Round |
| 9 | Sat 16 Sep 2023 | 10-1 v WalthamstowWalthamstow 1-0 Maldon & Tiptree | Isthmian League - North Division |
| 10 | Tue 21 Nov 2023 | 11-1 v Brightlingsea RegentBrightlingsea Regent 1-1 Maldon & Tiptree | Essex County Cup Third Round |
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