| 1 | Tue 30 Oct 2018 | 10 4-1 v Bury TownBury Town 1-4 Maldon & Tiptree | Bostik League North Division |
| 2 | Sat 3 Nov 2018 | 10 1-0 v Soham Town RangersMaldon & Tiptree 1-0 Soham Town Rangers | Bostik League North Division |
| 3 | Tue 6 Nov 2018 | 90-2 v Brentwood TownBrentwood Town 2-0 Maldon & Tiptree | Essex County Cup Third Round |
| 4 | Tue 27 Nov 2018 | 91-2 v Enfield TownMaldon & Tiptree 1-2 Enfield Town | Velocity Trophy Third Round |
| 5 | Sat 1 Dec 2018 | 9 4-1 v RomfordMaldon & Tiptree 4-1 Romford | Bostik League North Division |
| 6 | Sat 8 Dec 2018 | 92-1 v Basildon UnitedBasildon United 1-2 Maldon & Tiptree | Bostik League North Division |
| 7 | Sat 15 Dec 2018 | 92-1 v Felixstowe & Walton UnitedMaldon & Tiptree 2-1 Felixstowe & Walton United | Bostik League North Division |
| 8 | Wed 26 Dec 2018 | 91-1 v Heybridge SwiftsHeybridge Swifts 1-1 Maldon & Tiptree | Bostik League North Division |
| 9 | Sat 29 Dec 2018 | 160-1 v Witham TownMaldon & Tiptree 0-1 Witham Town | Bostik League North Division |
| 10 | Sat 12 Jan 2019 | 82-2 v Grays AthleticMaldon & Tiptree 2-2 Grays Athletic | Bostik League North Division |
| 11 | Sat 19 Jan 2019 | 145-1 v Mildenhall TownMaldon & Tiptree 5-1 Mildenhall Town | Bostik League North Division |
| 12 | Fri 25 Jan 2019 | 141-0 v Brentwood TownBrentwood Town 0-1 Maldon & Tiptree | Bostik League North Division |
| 13 | Sat 2 Feb 2019 | 73-0 v WhitehawkBrightlingsea Regent 3-0 Whitehawk | Bostik League Premier Division |
| 14 | Mon 4 Feb 2019 | 111-2 v Haringey BoroughHaringey Borough 2-1 Brightlingsea Regent | Bostik League Premier Division |
| 15 | Sat 9 Feb 2019 | 9 1-1 v MersthamBrightlingsea Regent 1-1 Merstham | Bostik League Premier Division |
| 16 | Sat 16 Feb 2019 | 80-1 v MargateMargate 1-0 Brightlingsea Regent | Bostik League Premier Division |
| 17 | Sat 23 Feb 2019 | 72-0 v KingstonianBrightlingsea Regent 2-0 Kingstonian | Bostik League Premier Division |
| 18 | Sat 2 Mar 2019 | 7 1-1 v Harlow TownBrightlingsea Regent 1-1 Harlow Town | Bostik League Premier Division |
| 19 | Sat 9 Mar 2019 | 14 1-1 v WorthingWorthing 1-1 Brightlingsea Regent | Bostik League Premier Division |
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