| 1 | Sat 23 Nov 2019 | 63-4 v Enfield TownEnfield Town 4-3 Maldon & Tiptree | Buildbase FA Trophy Third Qualifying Round |
| 2 | Wed 4 Dec 2019 | 54-0 v Witham TownWitham Town 0-4 Maldon & Tiptree | Essex County Cup Fourth Round |
| 3 | Tue 10 Dec 2019 | 68-1 v Heybridge SwiftsHeybridge Swifts 1-8 Maldon & Tiptree | Velocity Trophy Group 1 |
| 4 | Sat 14 Dec 2019 | 5 2-1 v Dereham TownMaldon & Tiptree 2-1 Dereham Town | BetVictor Isthmian North Division |
| 5 | Thu 26 Dec 2019 | 52-1 v Heybridge SwiftsMaldon & Tiptree 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 6 | Sat 28 Dec 2019 | 55-0 v Witham TownWitham Town 0-5 Maldon & Tiptree | BetVictor Isthmian North Division |
| 7 | Sat 4 Jan 2020 | 53-1 v AveleyMaldon & Tiptree 3-1 Aveley | BetVictor Isthmian North Division |
| 8 | Mon 6 Jan 2020 | 163-2 v Haringey BoroughHaringey Borough 2-3 Maldon & Tiptree | Velocity Trophy |
| 9 | Sat 11 Jan 2020 | 61-0 v Great Wakering RoversGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 10 | Sat 18 Jan 2020 | 151-2 v TilburyMaldon & Tiptree 1-2 Tilbury | BetVictor Isthmian North Division |
| 11 | Tue 21 Jan 2020 | 51-5 v Waltham AbbeyWaltham Abbey 5-1 Maldon & Tiptree | Essex County Cup Quarter Final |
| 12 | Tue 28 Jan 2020 | 5 0-0 v MersthamMaldon & Tiptree 0-0 Merstham | Velocity Trophy |
| 13 | Sat 1 Feb 2020 | 56-2 v Felixstowe & Walton UnitedMaldon & Tiptree 6-2 Felixstowe & Walton United | BetVictor Isthmian North Division |
| 14 | Tue 4 Feb 2020 | 53-1 v Canvey IslandCanvey Island 1-3 Maldon & Tiptree | BetVictor Isthmian North Division |
| 15 | Sat 8 Feb 2020 | 65-0 v Hullbridge SportsMaldon & Tiptree 5-0 Hullbridge Sports | BetVictor Isthmian North Division |
| 16 | Sat 15 Feb 2020 | 62-1 v Dereham TownDereham Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 17 | Tue 18 Feb 2020 | 62-1 v Bury TownBury Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 18 | Sat 22 Feb 2020 | 62-1 v Grays AthleticGrays Athletic 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 19 | Tue 25 Feb 2020 | 61-3 v RomfordMaldon & Tiptree 1-3 Romford | BetVictor Isthmian North Division |
| 20 | Tue 3 Mar 2020 | 62-1 v TilburyTilbury 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 21 | Sat 7 Mar 2020 | 61-0 v HistonHiston 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 22 | Tue 10 Mar 2020 | 60-0 v Cambridge CityMaldon & Tiptree 0-0 Cambridge City | BetVictor Isthmian North Division |
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