| 1 | Sat 19 Jan 2019 | 95-1 v Mildenhall TownMaldon & Tiptree 5-1 Mildenhall Town | Bostik League North Division |
| 2 | Fri 25 Jan 2019 | 91-0 v Brentwood TownBrentwood Town 0-1 Maldon & Tiptree | Bostik League North Division |
| 3 | Sat 2 Feb 2019 | 103-0 v Bury TownMaldon & Tiptree 3-0 Bury Town | Bostik League North Division |
| 4 | Sat 9 Feb 2019 | 103-1 v AveleyAveley 1-3 Maldon & Tiptree | Bostik League North Division |
| 5 | Sat 16 Feb 2019 | 101-2 v Bowers & PitseaMaldon & Tiptree 1-2 Bowers & Pitsea | Bostik League North Division |
| 6 | Sat 23 Feb 2019 | 10 2-0 v Soham Town RangersSoham Town Rangers 0-2 Maldon & Tiptree | Bostik League North Division |
| 7 | Sat 2 Mar 2019 | 103-0 v Dereham TownMaldon & Tiptree 3-0 Dereham Town | Bostik League North Division |
| 8 | Tue 5 Mar 2019 | 105-1 v AFC SudburyAFC Sudbury 1-5 Maldon & Tiptree | Bostik League North Division |
| 9 | Sat 9 Mar 2019 | 103-2 v TilburyTilbury 2-3 Maldon & Tiptree | Bostik League North Division |
| 10 | Sat 16 Mar 2019 | 101-4 v Coggeshall TownMaldon & Tiptree 1-4 Coggeshall Town | Bostik League North Division |
| 11 | Sat 23 Mar 2019 | 104-2 v RomfordRomford 2-4 Maldon & Tiptree | Bostik League North Division |
| 12 | Sat 30 Mar 2019 | 92-3 v Felixstowe & Walton UnitedFelixstowe & Walton United 3-2 Maldon & Tiptree | Bostik League North Division |
| 13 | Sat 6 Apr 2019 | 91-0 v Basildon UnitedMaldon & Tiptree 1-0 Basildon United | Bostik League North Division |
| 14 | Sat 13 Apr 2019 | 122-2 v Canvey IslandCanvey Island 2-2 Maldon & Tiptree | Bostik League North Division |
| 15 | Fri 19 Apr 2019 | 143-1 v Great Wakering RoversMaldon & Tiptree 3-1 Great Wakering Rovers | Bostik League North Division |
| 16 | Mon 22 Apr 2019 | 111-1 v Witham TownWitham Town 1-1 Maldon & Tiptree | Bostik League North Division |
| 17 | Sat 27 Apr 2019 | 117-1 v BarkingMaldon & Tiptree 7-1 Barking | Bostik League North Division |
| 18 | Wed 1 May 2019 | 111-0 v Coggeshall TownMaldon & Tiptree 1-0 Coggeshall Town | Bostik League North Division Play-off Semi Final |
| 19 | Sun 5 May 2019 | 112-2 v Heybridge SwiftsMaldon & Tiptree 2-2 Heybridge Swifts | Bostik League North Division Play-off Final |
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