| 1 | Sat 17 Aug 2019 | 6 3-1 v Soham Town RangersMaldon & Tiptree 3-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 62-1 v Brentwood TownBrentwood Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 3 | Tue 3 Sep 2019 | 64-1 v Coggeshall TownMaldon & Tiptree 4-1 Coggeshall Town | Velocity Trophy Group 1 |
| 4 | Sat 7 Sep 2019 | 63-0 v HistonHiston 0-3 Maldon & Tiptree | Emirates FA Cup First Qualifying Round |
| 5 | Sat 14 Sep 2019 | 6 3-0 v Basildon UnitedMaldon & Tiptree 3-0 Basildon United | BetVictor Isthmian North Division |
| 6 | Tue 17 Sep 2019 | 65-0 v Canvey IslandMaldon & Tiptree 5-0 Canvey Island | BetVictor Isthmian North Division |
| 7 | Sat 5 Oct 2019 | 66-1 v Chertsey TownMaldon & Tiptree 6-1 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 8 | Tue 8 Oct 2019 | 67-1 v Wivenhoe TownMaldon & Tiptree 7-1 Wivenhoe Town | Essex County Cup Third Round |
| 9 | Sat 12 Oct 2019 | 65-2 v Cray Valley PMMaldon & Tiptree 5-2 Cray Valley PM | Buildbase FA Trophy Preliminary Round |
| 10 | Sat 19 Oct 2019 | 63-1 v Royston TownRoyston Town 1-3 Maldon & Tiptree | Emirates FA Cup Fourth Qualifying Round |
| 11 | Tue 22 Oct 2019 | 62-2 v AFC SudburyMaldon & Tiptree 2-2 AFC Sudbury | Velocity Trophy Group 1 |
| 12 | Sat 26 Oct 2019 | 63-0 v Cray WanderersMaldon & Tiptree 3-0 Cray Wanderers | Buildbase FA Trophy First Qualifying Round |
| 13 | Wed 13 Nov 2019 | 6 4-3 v Folkestone InvictaMaldon & Tiptree 4-3 Folkestone Invicta | Buildbase FA Trophy Second Qualifying Round |
| 14 | Sat 16 Nov 2019 | 61-1 v HistonMaldon & Tiptree 1-1 Histon | BetVictor Isthmian North Division |
| 15 | Fri 29 Nov 2019 | 60-1 v Newport CountyMaldon & Tiptree 0-1 Newport County | Emirates FA Cup Second Round |
| 16 | Wed 4 Dec 2019 | 64-0 v Witham TownWitham Town 0-4 Maldon & Tiptree | Essex County Cup Fourth Round |
| 17 | Sat 7 Dec 2019 | 61-0 v Hullbridge SportsHullbridge Sports 0-1 Maldon & Tiptree | BetVictor Isthmian North Division |
| 18 | Sat 14 Dec 2019 | 62-1 v Dereham TownMaldon & Tiptree 2-1 Dereham Town | BetVictor Isthmian North Division |
| 19 | Thu 26 Dec 2019 | 62-1 v Heybridge SwiftsMaldon & Tiptree 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 20 | Sat 28 Dec 2019 | 155-0 v Witham TownWitham Town 0-5 Maldon & Tiptree | BetVictor Isthmian North Division |
| 21 | Sat 4 Jan 2020 | 6 3-1 v AveleyMaldon & Tiptree 3-1 Aveley | BetVictor Isthmian North Division |
| 22 | Mon 6 Jan 2020 | 63-2 v Haringey BoroughHaringey Borough 2-3 Maldon & Tiptree | Velocity Trophy |
| 23 | Sat 18 Jan 2020 | 6 1-2 v TilburyMaldon & Tiptree 1-2 Tilbury | BetVictor Isthmian North Division |
| 24 | Tue 21 Jan 2020 | 61-5 v Waltham AbbeyWaltham Abbey 5-1 Maldon & Tiptree | Essex County Cup Quarter Final |
| 25 | Tue 28 Jan 2020 | 60-0 v MersthamMaldon & Tiptree 0-0 Merstham | Velocity Trophy |
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