| 1 | Sat 1 Dec 2018 | 44-1 v RomfordMaldon & Tiptree 4-1 Romford | Bostik League North Division |
| 2 | Sat 15 Dec 2018 | 142-1 v Felixstowe & Walton UnitedMaldon & Tiptree 2-1 Felixstowe & Walton United | Bostik League North Division |
| 3 | Wed 26 Dec 2018 | 41-1 v Heybridge SwiftsHeybridge Swifts 1-1 Maldon & Tiptree | Bostik League North Division |
| 4 | Sat 29 Dec 2018 | 40-1 v Witham TownMaldon & Tiptree 0-1 Witham Town | Bostik League North Division |
| 5 | Sat 5 Jan 2019 | 114-2 v Great Wakering RoversGreat Wakering Rovers 2-4 Maldon & Tiptree | Bostik League North Division |
| 6 | Sat 12 Jan 2019 | 102-2 v Grays AthleticMaldon & Tiptree 2-2 Grays Athletic | Bostik League North Division |
| 7 | Sat 19 Jan 2019 | 85-1 v Mildenhall TownMaldon & Tiptree 5-1 Mildenhall Town | Bostik League North Division |
| 8 | Fri 25 Jan 2019 | 81-0 v Brentwood TownBrentwood Town 0-1 Maldon & Tiptree | Bostik League North Division |
| 9 | Sat 2 Feb 2019 | 163-0 v Bury TownMaldon & Tiptree 3-0 Bury Town | Bostik League North Division |
| 10 | Sat 16 Feb 2019 | 151-2 v Bowers & PitseaMaldon & Tiptree 1-2 Bowers & Pitsea | Bostik League North Division |
| 11 | Sat 23 Feb 2019 | 142-0 v Soham Town RangersSoham Town Rangers 0-2 Maldon & Tiptree | Bostik League North Division |
| 12 | Sat 2 Mar 2019 | 153-0 v Dereham TownMaldon & Tiptree 3-0 Dereham Town | Bostik League North Division |
| 13 | Tue 5 Mar 2019 | 155-1 v AFC SudburyAFC Sudbury 1-5 Maldon & Tiptree | Bostik League North Division |
| 14 | Sat 9 Mar 2019 | 113-2 v TilburyTilbury 2-3 Maldon & Tiptree | Bostik League North Division |
| 15 | Sat 16 Mar 2019 | 141-4 v Coggeshall TownMaldon & Tiptree 1-4 Coggeshall Town | Bostik League North Division |
| 16 | Sat 23 Mar 2019 | 74-2 v RomfordRomford 2-4 Maldon & Tiptree | Bostik League North Division |
| 17 | Sat 6 Apr 2019 | 151-0 v Basildon UnitedMaldon & Tiptree 1-0 Basildon United | Bostik League North Division |
| 18 | Sat 13 Apr 2019 | 82-2 v Canvey IslandCanvey Island 2-2 Maldon & Tiptree | Bostik League North Division |
| 19 | Sat 27 Apr 2019 | 87-1 v BarkingMaldon & Tiptree 7-1 Barking | Bostik League North Division |
| 20 | Sun 5 May 2019 | 152-2 v Heybridge SwiftsMaldon & Tiptree 2-2 Heybridge Swifts | Bostik League North Division Play-off Final |
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