| 1 | Sat 20 Oct 2018 | 40-0 v Bowers & PitseaBowers & Pitsea 0-0 Maldon & Tiptree | Bostik League North Division |
| 2 | Sat 3 Nov 2018 | 41-0 v Soham Town RangersMaldon & Tiptree 1-0 Soham Town Rangers | Bostik League North Division |
| 3 | Tue 6 Nov 2018 | 40-2 v Brentwood TownBrentwood Town 2-0 Maldon & Tiptree | Essex County Cup Third Round |
| 4 | Sat 10 Nov 2018 | 43-2 v Dereham TownDereham Town 2-3 Maldon & Tiptree | Bostik League North Division |
| 5 | Sat 17 Nov 2018 | 4 0-0 v TilburyMaldon & Tiptree 0-0 Tilbury | Bostik League North Division |
| 6 | Sat 24 Nov 2018 | 43-2 v Coggeshall TownCoggeshall Town 2-3 Maldon & Tiptree | Bostik League North Division |
| 7 | Tue 27 Nov 2018 | 41-2 v Enfield TownMaldon & Tiptree 1-2 Enfield Town | Velocity Trophy Third Round |
| 8 | Sat 8 Dec 2018 | 42-1 v Basildon UnitedBasildon United 1-2 Maldon & Tiptree | Bostik League North Division |
| 9 | Sat 15 Dec 2018 | 4 2-1 v Felixstowe & Walton UnitedMaldon & Tiptree 2-1 Felixstowe & Walton United | Bostik League North Division |
| 10 | Sat 12 Jan 2019 | 142-2 v Grays AthleticMaldon & Tiptree 2-2 Grays Athletic | Bostik League North Division |
| 11 | Sat 9 Feb 2019 | 143-1 v AveleyAveley 1-3 Maldon & Tiptree | Bostik League North Division |
| 12 | Sat 23 Feb 2019 | 42-0 v Soham Town RangersSoham Town Rangers 0-2 Maldon & Tiptree | Bostik League North Division |
| 13 | Sat 2 Mar 2019 | 43-0 v Dereham TownMaldon & Tiptree 3-0 Dereham Town | Bostik League North Division |
| 14 | Tue 5 Mar 2019 | 45-1 v AFC SudburyAFC Sudbury 1-5 Maldon & Tiptree | Bostik League North Division |
| 15 | Sat 9 Mar 2019 | 43-2 v TilburyTilbury 2-3 Maldon & Tiptree | Bostik League North Division |
| 16 | Sat 16 Mar 2019 | 41-4 v Coggeshall TownMaldon & Tiptree 1-4 Coggeshall Town | Bostik League North Division |
| 17 | Sat 23 Mar 2019 | 44-2 v RomfordRomford 2-4 Maldon & Tiptree | Bostik League North Division |
| 18 | Sat 30 Mar 2019 | 42-3 v Felixstowe & Walton UnitedFelixstowe & Walton United 3-2 Maldon & Tiptree | Bostik League North Division |
| 19 | Sat 6 Apr 2019 | 41-0 v Basildon UnitedMaldon & Tiptree 1-0 Basildon United | Bostik League North Division |
| 20 | Fri 19 Apr 2019 | 43-1 v Great Wakering RoversMaldon & Tiptree 3-1 Great Wakering Rovers | Bostik League North Division |
| 21 | Mon 22 Apr 2019 | 41-1 v Witham TownWitham Town 1-1 Maldon & Tiptree | Bostik League North Division |
| 22 | Sat 27 Apr 2019 | 147-1 v BarkingMaldon & Tiptree 7-1 Barking | Bostik League North Division |
| 23 | Wed 1 May 2019 | 161-0 v Coggeshall TownMaldon & Tiptree 1-0 Coggeshall Town | Bostik League North Division Play-off Semi Final |
| 24 | Sun 5 May 2019 | 142-2 v Heybridge SwiftsMaldon & Tiptree 2-2 Heybridge Swifts | Bostik League North Division Play-off Final |
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