| 1 | Sat 17 Aug 2019 | 72-1 v East Grinstead TownEast Grinstead Town 1-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 2 | Tue 20 Aug 2019 | 75-1 v Burgess Hill TownHaywards Heath Town 5-1 Burgess Hill Town | BetVictor Isthmian South East Division |
| 3 | Sat 24 Aug 2019 | 7 2-1 v Tunbridge WellsHaywards Heath Town 2-1 Tunbridge Wells | Emirates FA Cup Preliminary Round |
| 4 | Sat 14 Sep 2019 | 151-1 v Whitstable TownWhitstable Town 1-1 Haywards Heath Town | BetVictor Isthmian South East Division |
| 5 | Sat 28 Sep 2019 | 122-2 v RamsgateRamsgate 2-2 Haywards Heath Town | Buildbase FA Trophy Extra Preliminary Round |
| 6 | Tue 1 Oct 2019 | 121-0 v RamsgateHaywards Heath Town 1-0 Ramsgate | Buildbase FA Trophy Extra Preliminary Round |
| 7 | Sat 5 Oct 2019 | 70-2 v Hythe TownHythe Town 2-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 8 | Tue 8 Oct 2019 | 72-0 v East Grinstead TownEast Grinstead Town 0-2 Haywards Heath Town | Velocity Trophy Group 4 |
| 9 | Sat 12 Oct 2019 | 7 2-1 v Bracknell TownHaywards Heath Town 2-1 Bracknell Town | Buildbase FA Trophy Preliminary Round |
| 10 | Sat 19 Oct 2019 | 71-1 v Hastings UnitedHaywards Heath Town 1-1 Hastings United | BetVictor Isthmian South East Division |
| 11 | Tue 22 Oct 2019 | 70-1 v Hastings UnitedHastings United 1-0 Haywards Heath Town | Velocity Trophy Group 4 |
| 12 | Wed 6 Nov 2019 | 7 2-5 v WorthingHaywards Heath Town 2-5 Worthing | Sussex County Cup Second Round |
| 13 | Sat 9 Nov 2019 | 7 0-7 v Royston TownRoyston Town 7-0 Haywards Heath Town | Buildbase FA Trophy Second Qualifying Round |
| 14 | Tue 12 Nov 2019 | 7 1-1 v Three BridgesHaywards Heath Town 1-1 Three Bridges | Velocity Trophy Group 4 |
| 15 | Sat 16 Nov 2019 | 7 2-1 v RamsgateHaywards Heath Town 2-1 Ramsgate | BetVictor Isthmian South East Division |
| 16 | Tue 19 Nov 2019 | 72-0 v Chichester CityHaywards Heath Town 2-0 Chichester City | Velocity Trophy Group 4 |
| 17 | Sat 30 Nov 2019 | 7 2-2 v VCD AthleticVCD Athletic 2-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 18 | Sat 7 Dec 2019 | 71-0 v Ashford UnitedHaywards Heath Town 1-0 Ashford United | BetVictor Isthmian South East Division |
| 19 | Sat 21 Dec 2019 | 7 0-2 v WhyteleafeWhyteleafe 2-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 20 | Sat 28 Dec 2019 | 72-2 v WhitehawkHaywards Heath Town 2-2 Whitehawk | BetVictor Isthmian South East Division |
| 21 | Sat 4 Jan 2020 | 73-1 v Three BridgesThree Bridges 1-3 Haywards Heath Town | BetVictor Isthmian South East Division |
| 22 | Sat 11 Jan 2020 | 7 3-1 v Cray Valley PMHaywards Heath Town 3-1 Cray Valley PM | BetVictor Isthmian South East Division |
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