| 1 | 27/10/2018 | 2 1-3 v GuernseyGuernsey 3-1 Haywards Heath Town | Bostik League South East Division |
| 2 | 3/11/2018 | 110-1 v Cray WanderersHaywards Heath Town 0-1 Cray Wanderers | Bostik League South East Division |
| 3 | 6/11/2018 | 113-1 v Crawley TownCrawley Town 1-3 Haywards Heath Town | Sussex County Cup Second Round |
| 4 | 10/11/2018 | 113-2 v WhyteleafeWhyteleafe 2-3 Haywards Heath Town | Bostik League South East Division |
| 5 | 17/11/2018 | 111-0 v Herne BayHerne Bay 0-1 Haywards Heath Town | Bostik League South East Division |
| 6 | 24/11/2018 | 112-2 v Phoenix SportsHaywards Heath Town 2-2 Phoenix Sports | Bostik League South East Division |
| 7 | 1/12/2018 | 114-1 v Greenwich BoroughGreenwich Borough 1-4 Haywards Heath Town | Bostik League South East Division |
| 8 | 4/12/2018 | 114-0 v Little CommonLittle Common 0-4 Haywards Heath Town | Sussex County Cup Third Round |
| 9 | 8/12/2018 | 11 2-1 v Hastings UnitedHaywards Heath Town 2-1 Hastings United | Bostik League South East Division |
| 10 | 22/12/2018 | 112-0 v HorshamHaywards Heath Town 2-0 Horsham | Bostik League South East Division |
| 11 | 29/12/2018 | 11 3-3 v East Grinstead TownEast Grinstead Town 3-3 Haywards Heath Town | Bostik League South East Division |
| 12 | 5/1/2019 | 14 2-3 v RamsgateHaywards Heath Town 2-3 Ramsgate | Bostik League South East Division |
| 13 | 12/1/2019 | 110-0 v Hythe TownHythe Town 0-0 Haywards Heath Town | Bostik League South East Division |
| 14 | 15/1/2019 | 11 3-1 v East PrestonHaywards Heath Town 3-1 East Preston | Sussex County Cup Quarter Final |
| 15 | 19/1/2019 | 111-2 v GuernseyHaywards Heath Town 1-2 Guernsey | Bostik League South East Division |
| 16 | 26/1/2019 | 112-1 v SittingbourneSittingbourne 1-2 Haywards Heath Town | Bostik League South East Division |
| 17 | 5/2/2019 | 11 4-3 v Three BridgesThree Bridges 3-4 Haywards Heath Town | Bostik League South East Division |
| 18 | 9/2/2019 | 112-1 v Herne BayHaywards Heath Town 2-1 Herne Bay | Bostik League South East Division |
| 19 | 16/2/2019 | 114-2 v Phoenix SportsPhoenix Sports 2-4 Haywards Heath Town | Bostik League South East Division |
| 20 | 19/2/2019 | 112-0 v Faversham TownHaywards Heath Town 2-0 Faversham Town | Bostik League South East Division |
| 21 | 23/2/2019 | 120-0 v Greenwich BoroughHaywards Heath Town 0-0 Greenwich Borough | Bostik League South East Division |
| 22 | 27/2/2019 | 111-2 v Burgess Hill TownHaywards Heath Town 1-2 Burgess Hill Town | Sussex County Cup Semi Final |
| 23 | 2/3/2019 | 34-2 v Hastings UnitedHastings United 2-4 Haywards Heath Town | Bostik League South East Division |
| 24 | 16/3/2019 | 33-1 v WhyteleafeHaywards Heath Town 3-1 Whyteleafe | Bostik League South East Division |
| 25 | 23/3/2019 | 22-2 v Cray WanderersCray Wanderers 2-2 Haywards Heath Town | Bostik League South East Division |
| 26 | 30/3/2019 | 20-3 v VCD AthleticVCD Athletic 3-0 Haywards Heath Town | Bostik League South East Division |
| 27 | 6/4/2019 | 112-1 v Whitstable TownHaywards Heath Town 2-1 Whitstable Town | Bostik League South East Division |
| 28 | 13/4/2019 | 11 0-1 v Sevenoaks TownHaywards Heath Town 0-1 Sevenoaks Town | Bostik League South East Division |
| 29 | 20/4/2019 | 110-0 v RamsgateRamsgate 0-0 Haywards Heath Town | Bostik League South East Division |
| 30 | 22/4/2019 | 123-1 v East Grinstead TownHaywards Heath Town 3-1 East Grinstead Town | Bostik League South East Division |
| 31 | 27/4/2019 | 110-5 v Ashford UnitedAshford United 5-0 Haywards Heath Town | Bostik League South East Division |
| 32 | 29/4/2019 | 11 0-3 v HorshamHorsham 3-0 Haywards Heath Town | Bostik League South East Division Play-off Semi Final |
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