| 1 | Sat 17 Aug 2019 | 12-1 v East Grinstead TownEast Grinstead Town 1-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 2 | Tue 20 Aug 2019 | 15-1 v Burgess Hill TownHaywards Heath Town 5-1 Burgess Hill Town | BetVictor Isthmian South East Division |
| 3 | Sat 24 Aug 2019 | 1 2-1 v Tunbridge WellsHaywards Heath Town 2-1 Tunbridge Wells | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 11-1 v WhitehawkWhitehawk 1-1 Haywards Heath Town | BetVictor Isthmian South East Division |
| 5 | Sat 31 Aug 2019 | 10-2 v Three BridgesHaywards Heath Town 0-2 Three Bridges | BetVictor Isthmian South East Division |
| 6 | Tue 3 Sep 2019 | 10-2 v Burgess Hill TownBurgess Hill Town 2-0 Haywards Heath Town | Velocity Trophy Group 4 |
| 7 | Sat 7 Sep 2019 | 10-1 v Hayes & Yeading UnitedHaywards Heath Town 0-1 Hayes & Yeading United | Emirates FA Cup First Qualifying Round |
| 8 | Sat 14 Sep 2019 | 11-1 v Whitstable TownWhitstable Town 1-1 Haywards Heath Town | BetVictor Isthmian South East Division |
| 9 | Tue 17 Sep 2019 | 11-1 v GuernseyHaywards Heath Town 1-1 Guernsey | BetVictor Isthmian South East Division |
| 10 | Sat 28 Sep 2019 | 12-2 v RamsgateRamsgate 2-2 Haywards Heath Town | Buildbase FA Trophy Extra Preliminary Round |
| 11 | Tue 1 Oct 2019 | 11-0 v RamsgateHaywards Heath Town 1-0 Ramsgate | Buildbase FA Trophy Extra Preliminary Round |
| 12 | Sat 5 Oct 2019 | 10-2 v Hythe TownHythe Town 2-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 13 | Tue 8 Oct 2019 | 12-0 v East Grinstead TownEast Grinstead Town 0-2 Haywards Heath Town | Velocity Trophy Group 4 |
| 14 | Sat 12 Oct 2019 | 12-1 v Bracknell TownHaywards Heath Town 2-1 Bracknell Town | Buildbase FA Trophy Preliminary Round |
| 15 | Sat 19 Oct 2019 | 11-1 v Hastings UnitedHaywards Heath Town 1-1 Hastings United | BetVictor Isthmian South East Division |
| 16 | Tue 22 Oct 2019 | 10-1 v Hastings UnitedHastings United 1-0 Haywards Heath Town | Velocity Trophy Group 4 |
| 17 | Sat 26 Oct 2019 | 13-1 v Aylesbury UnitedHaywards Heath Town 3-1 Aylesbury United | Buildbase FA Trophy First Qualifying Round |
| 18 | Wed 6 Nov 2019 | 12-5 v WorthingHaywards Heath Town 2-5 Worthing | Sussex County Cup Second Round |
| 19 | Sat 9 Nov 2019 | 10-7 v Royston TownRoyston Town 7-0 Haywards Heath Town | Buildbase FA Trophy Second Qualifying Round |
| 20 | Tue 12 Nov 2019 | 11-1 v Three BridgesHaywards Heath Town 1-1 Three Bridges | Velocity Trophy Group 4 |
| 21 | Sat 16 Nov 2019 | 12-1 v RamsgateHaywards Heath Town 2-1 Ramsgate | BetVictor Isthmian South East Division |
| 22 | Tue 19 Nov 2019 | 12-0 v Chichester CityHaywards Heath Town 2-0 Chichester City | Velocity Trophy Group 4 |
| 23 | Sat 30 Nov 2019 | 12-2 v VCD AthleticVCD Athletic 2-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 24 | Sat 7 Dec 2019 | 11-0 v Ashford UnitedHaywards Heath Town 1-0 Ashford United | BetVictor Isthmian South East Division |
| 25 | Sat 14 Dec 2019 | 10-0 v Herne BayHerne Bay 0-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 26 | Sat 21 Dec 2019 | 10-2 v WhyteleafeWhyteleafe 2-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 27 | Sat 28 Dec 2019 | 12-2 v WhitehawkHaywards Heath Town 2-2 Whitehawk | BetVictor Isthmian South East Division |
| 28 | Sat 4 Jan 2020 | 1 3-1 v Three BridgesThree Bridges 1-3 Haywards Heath Town | BetVictor Isthmian South East Division |
| 29 | Sat 11 Jan 2020 | 13-1 v Cray Valley PMHaywards Heath Town 3-1 Cray Valley PM | BetVictor Isthmian South East Division |
| 30 | Sat 18 Jan 2020 | 1 0-1 v Hastings UnitedHastings United 1-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 31 | Tue 21 Jan 2020 | 10-1 v Phoenix SportsPhoenix Sports 1-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 32 | Sat 25 Jan 2020 | 10-3 v Hythe TownHaywards Heath Town 0-3 Hythe Town | BetVictor Isthmian South East Division |
| 33 | Wed 5 Feb 2020 | 12-2 v GuernseyGuernsey 2-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 34 | Sat 8 Feb 2020 | 10-2 v Herne BayHaywards Heath Town 0-2 Herne Bay | BetVictor Isthmian South East Division |
| 35 | Sat 15 Feb 2020 | 11-1 v Ashford UnitedAshford United 1-1 Haywards Heath Town | BetVictor Isthmian South East Division |
| 36 | Tue 18 Feb 2020 | 12-1 v Sevenoaks TownSevenoaks Town 1-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 37 | Sat 22 Feb 2020 | 11-0 v Sevenoaks TownHaywards Heath Town 1-0 Sevenoaks Town | BetVictor Isthmian South East Division |
| 38 | Tue 25 Feb 2020 | 15-1 v Faversham TownHaywards Heath Town 5-1 Faversham Town | BetVictor Isthmian South East Division |
| 39 | Tue 3 Mar 2020 | 12-1 v SittingbourneHaywards Heath Town 2-1 Sittingbourne | BetVictor Isthmian South East Division |
| 40 | Sat 7 Mar 2020 | 10-1 v Phoenix SportsHaywards Heath Town 0-1 Phoenix Sports | BetVictor Isthmian South East Division |
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