| 1 | Thu 26 Dec 2019 | 42-1 v Heybridge SwiftsMaldon & Tiptree 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 2 | Sat 28 Dec 2019 | 45-0 v Witham TownWitham Town 0-5 Maldon & Tiptree | BetVictor Isthmian North Division |
| 3 | Sat 4 Jan 2020 | 43-1 v AveleyMaldon & Tiptree 3-1 Aveley | BetVictor Isthmian North Division |
| 4 | Mon 6 Jan 2020 | 8 3-2 v Haringey BoroughHaringey Borough 2-3 Maldon & Tiptree | Velocity Trophy |
| 5 | Sat 11 Jan 2020 | 71-0 v Great Wakering RoversGreat Wakering Rovers 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 6 | Sat 18 Jan 2020 | 71-2 v TilburyMaldon & Tiptree 1-2 Tilbury | BetVictor Isthmian North Division |
| 7 | Tue 28 Jan 2020 | 80-0 v MersthamMaldon & Tiptree 0-0 Merstham | Velocity Trophy |
| 8 | Sat 1 Feb 2020 | 66-2 v Felixstowe & Walton UnitedMaldon & Tiptree 6-2 Felixstowe & Walton United | BetVictor Isthmian North Division |
| 9 | Tue 4 Feb 2020 | 73-1 v Canvey IslandCanvey Island 1-3 Maldon & Tiptree | BetVictor Isthmian North Division |
| 10 | Sat 8 Feb 2020 | 4 5-0 v Hullbridge SportsMaldon & Tiptree 5-0 Hullbridge Sports | BetVictor Isthmian North Division |
| 11 | Tue 11 Feb 2020 | 140-0 v Bracknell TownBracknell Town 0-0 Maldon & Tiptree | Velocity Trophy Quarter Final |
| 12 | Tue 18 Feb 2020 | 72-1 v Bury TownBury Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 13 | Sat 22 Feb 2020 | 152-1 v Grays AthleticGrays Athletic 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 14 | Tue 3 Mar 2020 | 42-1 v TilburyTilbury 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 15 | Sat 7 Mar 2020 | 41-0 v HistonHiston 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 16 | Tue 10 Mar 2020 | 5 0-0 v Cambridge CityMaldon & Tiptree 0-0 Cambridge City | BetVictor Isthmian North Division |
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