| 1 | Mon 27 Aug 2018 | 155-4 v HorshamHorsham 4-5 Haywards Heath Town | Bostik League South East Division |
| 2 | Tue 18 Sep 2018 | 160-0 v Whitstable TownWhitstable Town 0-0 Haywards Heath Town | Bostik League South East Division |
| 3 | Tue 25 Sep 2018 | 142-0 v Three BridgesHaywards Heath Town 2-0 Three Bridges | Bostik League South East Division |
| 4 | Sat 29 Sep 2018 | 24-4 v Ashford UnitedAshford United 4-4 Haywards Heath Town | Buildbase FA Trophy Extra Preliminary Round |
| 5 | Tue 2 Oct 2018 | 143-0 v Ashford UnitedHaywards Heath Town 3-0 Ashford United | Buildbase FA Trophy Extra Preliminary Round Replay |
| 6 | Sat 6 Oct 2018 | 22-0 v SittingbourneHaywards Heath Town 2-0 Sittingbourne | Bostik League South East Division |
| 7 | Sat 13 Oct 2018 | 22-3 v Bracknell TownHaywards Heath Town 2-3 Bracknell Town | Buildbase FA Trophy Preliminary Round |
| 8 | Sat 20 Oct 2018 | 104-2 v Faversham TownFaversham Town 2-4 Haywards Heath Town | Bostik League South East Division |
| 9 | Sat 27 Oct 2018 | 101-3 v GuernseyGuernsey 3-1 Haywards Heath Town | Bostik League South East Division |
| 10 | Sat 3 Nov 2018 | 20-1 v Cray WanderersHaywards Heath Town 0-1 Cray Wanderers | Bostik League South East Division |
| 11 | Tue 6 Nov 2018 | 23-1 v Crawley TownCrawley Town 1-3 Haywards Heath Town | Sussex County Cup Second Round |
| 12 | Sat 10 Nov 2018 | 23-2 v WhyteleafeWhyteleafe 2-3 Haywards Heath Town | Bostik League South East Division |
| 13 | Sat 17 Nov 2018 | 21-0 v Herne BayHerne Bay 0-1 Haywards Heath Town | Bostik League South East Division |
| 14 | Tue 4 Dec 2018 | 34-0 v Little CommonLittle Common 0-4 Haywards Heath Town | Sussex County Cup Third Round |
| 15 | Sat 8 Dec 2018 | 32-1 v Hastings UnitedHaywards Heath Town 2-1 Hastings United | Bostik League South East Division |
| 16 | Sat 22 Dec 2018 | 32-0 v HorshamHaywards Heath Town 2-0 Horsham | Bostik League South East Division |
| 17 | Sat 29 Dec 2018 | 33-3 v East Grinstead TownEast Grinstead Town 3-3 Haywards Heath Town | Bostik League South East Division |
| 18 | Sat 12 Jan 2019 | 30-0 v Hythe TownHythe Town 0-0 Haywards Heath Town | Bostik League South East Division |
| 19 | Tue 15 Jan 2019 | 123-1 v East PrestonHaywards Heath Town 3-1 East Preston | Sussex County Cup Quarter Final |
| 20 | Tue 19 Feb 2019 | 142-0 v Faversham TownHaywards Heath Town 2-0 Faversham Town | Bostik League South East Division |
| 21 | Sat 23 Feb 2019 | 30-0 v Greenwich BoroughHaywards Heath Town 0-0 Greenwich Borough | Bostik League South East Division |
| 22 | Sat 23 Mar 2019 | 122-2 v Cray WanderersCray Wanderers 2-2 Haywards Heath Town | Bostik League South East Division |
| 23 | Sat 30 Mar 2019 | 150-3 v VCD AthleticVCD Athletic 3-0 Haywards Heath Town | Bostik League South East Division |
| 24 | Sat 6 Apr 2019 | 22-1 v Whitstable TownHaywards Heath Town 2-1 Whitstable Town | Bostik League South East Division |
| 25 | Sat 13 Apr 2019 | 20-1 v Sevenoaks TownHaywards Heath Town 0-1 Sevenoaks Town | Bostik League South East Division |
| 26 | Sat 20 Apr 2019 | 120-0 v RamsgateRamsgate 0-0 Haywards Heath Town | Bostik League South East Division |
| 27 | Mon 22 Apr 2019 | 23-1 v East Grinstead TownHaywards Heath Town 3-1 East Grinstead Town | Bostik League South East Division |
| 28 | Mon 29 Apr 2019 | 30-3 v HorshamHorsham 3-0 Haywards Heath Town | Bostik League South East Division Play-off Semi Final |
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