| 1 | 17/8/2019 | 8 3-1 v Soham Town RangersMaldon & Tiptree 3-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 2 | 20/8/2019 | 82-1 v Brentwood TownBrentwood Town 1-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 3 | 24/8/2019 | 82-1 v Saffron Walden TownSaffron Walden Town 1-2 Maldon & Tiptree | Emirates FA Cup Preliminary Round |
| 4 | 26/8/2019 | 85-1 v Witham TownMaldon & Tiptree 5-1 Witham Town | BetVictor Isthmian North Division |
| 5 | 31/8/2019 | 82-0 v AveleyAveley 0-2 Maldon & Tiptree | BetVictor Isthmian North Division |
| 6 | 3/9/2019 | 84-1 v Coggeshall TownMaldon & Tiptree 4-1 Coggeshall Town | Velocity Trophy Group 1 |
| 7 | 7/9/2019 | 83-0 v HistonHiston 0-3 Maldon & Tiptree | Emirates FA Cup First Qualifying Round |
| 8 | 14/9/2019 | 83-0 v Basildon UnitedMaldon & Tiptree 3-0 Basildon United | BetVictor Isthmian North Division |
| 9 | 17/9/2019 | 85-0 v Canvey IslandMaldon & Tiptree 5-0 Canvey Island | BetVictor Isthmian North Division |
| 10 | 21/9/2019 | 84-2 v Wingate & FinchleyMaldon & Tiptree 4-2 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 11 | 28/9/2019 | 85-0 v Felixstowe & Walton UnitedMaldon & Tiptree 5-0 Felixstowe & Walton United | Buildbase FA Trophy Extra Preliminary Round |
| 12 | 5/10/2019 | 86-1 v Chertsey TownMaldon & Tiptree 6-1 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 13 | 12/10/2019 | 85-2 v Cray Valley PMMaldon & Tiptree 5-2 Cray Valley PM | Buildbase FA Trophy Preliminary Round |
| 14 | 19/10/2019 | 83-1 v Royston TownRoyston Town 1-3 Maldon & Tiptree | Emirates FA Cup Fourth Qualifying Round |
| 15 | 22/10/2019 | 162-2 v AFC SudburyMaldon & Tiptree 2-2 AFC Sudbury | Velocity Trophy Group 1 |
| 16 | 26/10/2019 | 83-0 v Cray WanderersMaldon & Tiptree 3-0 Cray Wanderers | Buildbase FA Trophy First Qualifying Round |
| 17 | 2/11/2019 | 83-1 v Grays AthleticMaldon & Tiptree 3-1 Grays Athletic | BetVictor Isthmian North Division |
| 18 | 13/11/2019 | 84-3 v Folkestone InvictaMaldon & Tiptree 4-3 Folkestone Invicta | Buildbase FA Trophy Second Qualifying Round |
| 19 | 16/11/2019 | 81-1 v HistonMaldon & Tiptree 1-1 Histon | BetVictor Isthmian North Division |
| 20 | 19/11/2019 | 146-1 v Bury TownMaldon & Tiptree 6-1 Bury Town | Velocity Trophy Group 1 |
| 21 | 23/11/2019 | 8 3-4 v Enfield TownEnfield Town 4-3 Maldon & Tiptree | Buildbase FA Trophy Third Qualifying Round |
| 22 | 29/11/2019 | 8 0-1 v Newport CountyMaldon & Tiptree 0-1 Newport County | Emirates FA Cup Second Round |
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