| 1 | Sat 15 Sep 2018 | 162-2 v Sevenoaks TownSevenoaks Town 2-2 Haywards Heath Town | Bostik League South East Division |
| 2 | Tue 18 Sep 2018 | 12 0-0 v Whitstable TownWhitstable Town 0-0 Haywards Heath Town | Bostik League South East Division |
| 3 | Sat 22 Sep 2018 | 151-1 v Ashford UnitedHaywards Heath Town 1-1 Ashford United | Bostik League South East Division |
| 4 | Tue 25 Sep 2018 | 122-0 v Three BridgesHaywards Heath Town 2-0 Three Bridges | Bostik League South East Division |
| 5 | Sat 29 Sep 2018 | 124-4 v Ashford UnitedAshford United 4-4 Haywards Heath Town | Buildbase FA Trophy Extra Preliminary Round |
| 6 | Sat 6 Oct 2018 | 32-0 v SittingbourneHaywards Heath Town 2-0 Sittingbourne | Bostik League South East Division |
| 7 | Sat 13 Oct 2018 | 5 2-3 v Bracknell TownHaywards Heath Town 2-3 Bracknell Town | Buildbase FA Trophy Preliminary Round |
| 8 | Sat 20 Oct 2018 | 124-2 v Faversham TownFaversham Town 2-4 Haywards Heath Town | Bostik League South East Division |
| 9 | Sat 27 Oct 2018 | 161-3 v GuernseyGuernsey 3-1 Haywards Heath Town | Bostik League South East Division |
| 10 | Sat 29 Dec 2018 | 163-3 v East Grinstead TownEast Grinstead Town 3-3 Haywards Heath Town | Bostik League South East Division |
| 11 | Sat 5 Jan 2019 | 52-3 v RamsgateHaywards Heath Town 2-3 Ramsgate | Bostik League South East Division |
| 12 | Sat 12 Jan 2019 | 180-0 v Hythe TownHythe Town 0-0 Haywards Heath Town | Bostik League South East Division |
| 13 | Tue 15 Jan 2019 | 193-1 v East PrestonHaywards Heath Town 3-1 East Preston | Sussex County Cup Quarter Final |
| 14 | Sat 19 Jan 2019 | 191-2 v GuernseyHaywards Heath Town 1-2 Guernsey | Bostik League South East Division |
| 15 | Sat 26 Jan 2019 | 12 2-1 v SittingbourneSittingbourne 1-2 Haywards Heath Town | Bostik League South East Division |
| 16 | Tue 5 Feb 2019 | 24-3 v Three BridgesThree Bridges 3-4 Haywards Heath Town | Bostik League South East Division |
| 17 | Sat 9 Feb 2019 | 19 2-1 v Herne BayHaywards Heath Town 2-1 Herne Bay | Bostik League South East Division |
| 18 | Sat 16 Feb 2019 | 144-2 v Phoenix SportsPhoenix Sports 2-4 Haywards Heath Town | Bostik League South East Division |
| 19 | Tue 19 Feb 2019 | 192-0 v Faversham TownHaywards Heath Town 2-0 Faversham Town | Bostik League South East Division |
| 20 | Sat 23 Feb 2019 | 160-0 v Greenwich BoroughHaywards Heath Town 0-0 Greenwich Borough | Bostik League South East Division |
| 21 | Wed 27 Feb 2019 | 191-2 v Burgess Hill TownHaywards Heath Town 1-2 Burgess Hill Town | Sussex County Cup Semi Final |
| 22 | Sat 2 Mar 2019 | 24-2 v Hastings UnitedHastings United 2-4 Haywards Heath Town | Bostik League South East Division |
| 23 | Sat 16 Mar 2019 | 193-1 v WhyteleafeHaywards Heath Town 3-1 Whyteleafe | Bostik League South East Division |
| 24 | Sat 13 Apr 2019 | 6 0-1 v Sevenoaks TownHaywards Heath Town 0-1 Sevenoaks Town | Bostik League South East Division |
| 25 | Sat 20 Apr 2019 | 20-0 v RamsgateRamsgate 0-0 Haywards Heath Town | Bostik League South East Division |
| 26 | Mon 22 Apr 2019 | 63-1 v East Grinstead TownHaywards Heath Town 3-1 East Grinstead Town | Bostik League South East Division |
| 27 | Mon 29 Apr 2019 | 190-3 v HorshamHorsham 3-0 Haywards Heath Town | Bostik League South East Division Play-off Semi Final |
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