| 1 | Sat 17 Aug 2019 | 53-1 v Soham Town RangersMaldon & Tiptree 3-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 52-1 v Brentwood TownBrentwood Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 52-1 v Saffron Walden TownSaffron Walden Town 1-2 Maldon & Tiptree | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 55-1 v Witham TownMaldon & Tiptree 5-1 Witham Town | BetVictor Isthmian North Division |
| 5 | Sat 31 Aug 2019 | 52-0 v AveleyAveley 0-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 6 | Sat 7 Sep 2019 | 33-0 v HistonHiston 0-3 Maldon & Tiptree | Emirates FA Cup First Qualifying Round |
| 7 | Tue 17 Sep 2019 | 55-0 v Canvey IslandMaldon & Tiptree 5-0 Canvey Island | BetVictor Isthmian North Division |
| 8 | Sat 21 Sep 2019 | 54-2 v Wingate & FinchleyMaldon & Tiptree 4-2 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 9 | Tue 24 Sep 2019 | 123-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-3 Maldon & Tiptree | Velocity Trophy Group 1 |
| 10 | Sat 28 Sep 2019 | 65-0 v Felixstowe & Walton UnitedMaldon & Tiptree 5-0 Felixstowe & Walton United | Buildbase FA Trophy Extra Preliminary Round |
| 11 | Sat 5 Oct 2019 | 56-1 v Chertsey TownMaldon & Tiptree 6-1 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 12 | Tue 8 Oct 2019 | 157-1 v Wivenhoe TownMaldon & Tiptree 7-1 Wivenhoe Town | Essex County Cup Third Round |
| 13 | Sat 12 Oct 2019 | 55-2 v Cray Valley PMMaldon & Tiptree 5-2 Cray Valley PM | Buildbase FA Trophy Preliminary Round |
| 14 | Sat 19 Oct 2019 | 53-1 v Royston TownRoyston Town 1-3 Maldon & Tiptree | Emirates FA Cup Fourth Qualifying Round |
| 15 | Tue 22 Oct 2019 | 152-2 v AFC SudburyMaldon & Tiptree 2-2 AFC Sudbury | Velocity Trophy Group 1 |
| 16 | Sat 26 Oct 2019 | 53-0 v Cray WanderersMaldon & Tiptree 3-0 Cray Wanderers | Buildbase FA Trophy First Qualifying Round |
| 17 | Tue 29 Oct 2019 | 5 2-0 v Felixstowe & Walton UnitedFelixstowe & Walton United 0-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 18 | Sat 2 Nov 2019 | 53-1 v Grays AthleticMaldon & Tiptree 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 19 | Tue 19 Nov 2019 | 56-1 v Bury TownMaldon & Tiptree 6-1 Bury Town | Velocity Trophy Group 1 |
| 20 | Sat 23 Nov 2019 | 53-4 v Enfield TownEnfield Town 4-3 Maldon & Tiptree | Buildbase FA Trophy Third Qualifying Round |
| 21 | Fri 29 Nov 2019 | 50-1 v Newport CountyMaldon & Tiptree 0-1 Newport County | Emirates FA Cup Second Round |
| 22 | Wed 4 Dec 2019 | 44-0 v Witham TownWitham Town 0-4 Maldon & Tiptree | Essex County Cup Fourth Round |
| 23 | Sat 7 Dec 2019 | 51-0 v Hullbridge SportsHullbridge Sports 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
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