| 1 | Sat 17 Aug 2019 | 163-1 v Soham Town RangersMaldon & Tiptree 3-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 2 | Tue 3 Sep 2019 | 54-1 v Coggeshall TownMaldon & Tiptree 4-1 Coggeshall Town | Velocity Trophy Group 1 |
| 3 | Sat 7 Sep 2019 | 53-0 v HistonHiston 0-3 Maldon & Tiptree | Emirates FA Cup First Qualifying Round |
| 4 | Sat 14 Sep 2019 | 153-0 v Basildon UnitedMaldon & Tiptree 3-0 Basildon United | BetVictor Isthmian North Division |
| 5 | Sat 21 Sep 2019 | 154-2 v Wingate & FinchleyMaldon & Tiptree 4-2 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 6 | Tue 24 Sep 2019 | 53-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-3 Maldon & Tiptree | Velocity Trophy Group 1 |
| 7 | Sat 28 Sep 2019 | 5 5-0 v Felixstowe & Walton UnitedMaldon & Tiptree 5-0 Felixstowe & Walton United | Buildbase FA Trophy Extra Preliminary Round |
| 8 | Tue 8 Oct 2019 | 57-1 v Wivenhoe TownMaldon & Tiptree 7-1 Wivenhoe Town | Essex County Cup Third Round |
| 9 | Sat 19 Oct 2019 | 153-1 v Royston TownRoyston Town 1-3 Maldon & Tiptree | Emirates FA Cup Fourth Qualifying Round |
| 10 | Tue 22 Oct 2019 | 52-2 v AFC SudburyMaldon & Tiptree 2-2 AFC Sudbury | Velocity Trophy Group 1 |
| 11 | Sat 26 Oct 2019 | 153-0 v Cray WanderersMaldon & Tiptree 3-0 Cray Wanderers | Buildbase FA Trophy First Qualifying Round |
| 12 | Tue 29 Oct 2019 | 62-0 v Felixstowe & Walton UnitedFelixstowe & Walton United 0-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 13 | Sat 2 Nov 2019 | 6 3-1 v Grays AthleticMaldon & Tiptree 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 14 | Wed 13 Nov 2019 | 54-3 v Folkestone InvictaMaldon & Tiptree 4-3 Folkestone Invicta | Buildbase FA Trophy Second Qualifying Round |
| 15 | Sat 16 Nov 2019 | 51-1 v HistonMaldon & Tiptree 1-1 Histon | BetVictor Isthmian North Division |
| 16 | Tue 19 Nov 2019 | 66-1 v Bury TownMaldon & Tiptree 6-1 Bury Town | Velocity Trophy Group 1 |
| 17 | Sat 23 Nov 2019 | 153-4 v Enfield TownEnfield Town 4-3 Maldon & Tiptree | Buildbase FA Trophy Third Qualifying Round |
| 18 | Fri 29 Nov 2019 | 15 0-1 v Newport CountyMaldon & Tiptree 0-1 Newport County | Emirates FA Cup Second Round |
| 19 | Sat 7 Dec 2019 | 151-0 v Hullbridge SportsHullbridge Sports 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 20 | Tue 10 Dec 2019 | 58-1 v Heybridge SwiftsHeybridge Swifts 1-8 Maldon & Tiptree | Velocity Trophy Group 1 |
| 21 | Sat 14 Dec 2019 | 152-1 v Dereham TownMaldon & Tiptree 2-1 Dereham Town | BetVictor Isthmian North Division |
| 22 | Sat 28 Dec 2019 | 65-0 v Witham TownWitham Town 0-5 Maldon & Tiptree | BetVictor Isthmian North Division |
| 23 | Sat 4 Jan 2020 | 153-1 v AveleyMaldon & Tiptree 3-1 Aveley | BetVictor Isthmian North Division |
| 24 | Mon 6 Jan 2020 | 53-2 v Haringey BoroughHaringey Borough 2-3 Maldon & Tiptree | Velocity Trophy |
| 25 | Sat 11 Jan 2020 | 51-0 v Great Wakering RoversGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 26 | Sat 18 Jan 2020 | 5 1-2 v TilburyMaldon & Tiptree 1-2 Tilbury | BetVictor Isthmian North Division |
| 27 | Tue 4 Feb 2020 | 63-1 v Canvey IslandCanvey Island 1-3 Maldon & Tiptree | BetVictor Isthmian North Division |
| 28 | Sat 8 Feb 2020 | 55-0 v Hullbridge SportsMaldon & Tiptree 5-0 Hullbridge Sports | BetVictor Isthmian North Division |
| 29 | Tue 11 Feb 2020 | 50-0 v Bracknell TownBracknell Town 0-0 Maldon & Tiptree | Velocity Trophy Quarter Final |
| 30 | Sat 15 Feb 2020 | 52-1 v Dereham TownDereham Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 31 | Tue 18 Feb 2020 | 5 2-1 v Bury TownBury Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 32 | Sat 22 Feb 2020 | 52-1 v Grays AthleticGrays Athletic 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 33 | Tue 3 Mar 2020 | 52-1 v TilburyTilbury 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
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