| 1 | Sat 17 Aug 2019 | 13-1 v Soham Town RangersMaldon & Tiptree 3-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 12-1 v Brentwood TownBrentwood Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 1 2-1 v Saffron Walden TownSaffron Walden Town 1-2 Maldon & Tiptree | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 15-1 v Witham TownMaldon & Tiptree 5-1 Witham Town | BetVictor Isthmian North Division |
| 5 | Sat 31 Aug 2019 | 12-0 v AveleyAveley 0-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 6 | Tue 3 Sep 2019 | 14-1 v Coggeshall TownMaldon & Tiptree 4-1 Coggeshall Town | Velocity Trophy Group 1 |
| 7 | Sat 7 Sep 2019 | 13-0 v HistonHiston 0-3 Maldon & Tiptree | Emirates FA Cup First Qualifying Round |
| 8 | Sat 14 Sep 2019 | 13-0 v Basildon UnitedMaldon & Tiptree 3-0 Basildon United | BetVictor Isthmian North Division |
| 9 | Tue 17 Sep 2019 | 15-0 v Canvey IslandMaldon & Tiptree 5-0 Canvey Island | BetVictor Isthmian North Division |
| 10 | Sat 21 Sep 2019 | 14-2 v Wingate & FinchleyMaldon & Tiptree 4-2 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 11 | Sat 28 Sep 2019 | 15-0 v Felixstowe & Walton UnitedMaldon & Tiptree 5-0 Felixstowe & Walton United | Buildbase FA Trophy Extra Preliminary Round |
| 12 | Sat 5 Oct 2019 | 16-1 v Chertsey TownMaldon & Tiptree 6-1 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 13 | Sat 12 Oct 2019 | 15-2 v Cray Valley PMMaldon & Tiptree 5-2 Cray Valley PM | Buildbase FA Trophy Preliminary Round |
| 14 | Sat 19 Oct 2019 | 13-1 v Royston TownRoyston Town 1-3 Maldon & Tiptree | Emirates FA Cup Fourth Qualifying Round |
| 15 | Sat 26 Oct 2019 | 13-0 v Cray WanderersMaldon & Tiptree 3-0 Cray Wanderers | Buildbase FA Trophy First Qualifying Round |
| 16 | Sat 2 Nov 2019 | 13-1 v Grays AthleticMaldon & Tiptree 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 17 | Wed 13 Nov 2019 | 14-3 v Folkestone InvictaMaldon & Tiptree 4-3 Folkestone Invicta | Buildbase FA Trophy Second Qualifying Round |
| 18 | Sat 16 Nov 2019 | 11-1 v HistonMaldon & Tiptree 1-1 Histon | BetVictor Isthmian North Division |
| 19 | Sat 23 Nov 2019 | 13-4 v Enfield TownEnfield Town 4-3 Maldon & Tiptree | Buildbase FA Trophy Third Qualifying Round |
| 20 | Fri 29 Nov 2019 | 10-1 v Newport CountyMaldon & Tiptree 0-1 Newport County | Emirates FA Cup Second Round |
| 21 | Sat 7 Dec 2019 | 11-0 v Hullbridge SportsHullbridge Sports 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 22 | Tue 10 Dec 2019 | 18-1 v Heybridge SwiftsHeybridge Swifts 1-8 Maldon & Tiptree | Velocity Trophy Group 1 |
| 23 | Sat 14 Dec 2019 | 12-1 v Dereham TownMaldon & Tiptree 2-1 Dereham Town | BetVictor Isthmian North Division |
| 24 | Thu 26 Dec 2019 | 12-1 v Heybridge SwiftsMaldon & Tiptree 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 25 | Sat 28 Dec 2019 | 15-0 v Witham TownWitham Town 0-5 Maldon & Tiptree | BetVictor Isthmian North Division |
| 26 | Sat 4 Jan 2020 | 13-1 v AveleyMaldon & Tiptree 3-1 Aveley | BetVictor Isthmian North Division |
| 27 | Sat 11 Jan 2020 | 11-0 v Great Wakering RoversGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 28 | Sat 18 Jan 2020 | 11-2 v TilburyMaldon & Tiptree 1-2 Tilbury | BetVictor Isthmian North Division |
| 29 | Tue 28 Jan 2020 | 10-0 v MersthamMaldon & Tiptree 0-0 Merstham | Velocity Trophy |
| 30 | Sat 1 Feb 2020 | 16-2 v Felixstowe & Walton UnitedMaldon & Tiptree 6-2 Felixstowe & Walton United | BetVictor Isthmian North Division |
| 31 | Tue 4 Feb 2020 | 1 3-1 v Canvey IslandCanvey Island 1-3 Maldon & Tiptree | BetVictor Isthmian North Division |
| 32 | Sat 8 Feb 2020 | 15-0 v Hullbridge SportsMaldon & Tiptree 5-0 Hullbridge Sports | BetVictor Isthmian North Division |
| 33 | Sat 15 Feb 2020 | 12-1 v Dereham TownDereham Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 34 | Tue 18 Feb 2020 | 12-1 v Bury TownBury Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 35 | Sat 22 Feb 2020 | 12-1 v Grays AthleticGrays Athletic 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 36 | Tue 25 Feb 2020 | 11-3 v RomfordMaldon & Tiptree 1-3 Romford | BetVictor Isthmian North Division |
| 37 | Tue 3 Mar 2020 | 12-1 v TilburyTilbury 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 38 | Sat 7 Mar 2020 | 11-0 v HistonHiston 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 39 | Tue 10 Mar 2020 | 10-0 v Cambridge CityMaldon & Tiptree 0-0 Cambridge City | BetVictor Isthmian North Division |
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