| 1 | Sat 17 Aug 2019 | 42-1 v East Grinstead TownEast Grinstead Town 1-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 2 | Tue 20 Aug 2019 | 45-1 v Burgess Hill TownHaywards Heath Town 5-1 Burgess Hill Town | BetVictor Isthmian South East Division |
| 3 | Sat 24 Aug 2019 | 42-1 v Tunbridge WellsHaywards Heath Town 2-1 Tunbridge Wells | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 41-1 v WhitehawkWhitehawk 1-1 Haywards Heath Town | BetVictor Isthmian South East Division |
| 5 | Tue 3 Sep 2019 | 6 0-2 v Burgess Hill TownBurgess Hill Town 2-0 Haywards Heath Town | Velocity Trophy Group 4 |
| 6 | Sat 7 Sep 2019 | 40-1 v Hayes & Yeading UnitedHaywards Heath Town 0-1 Hayes & Yeading United | Emirates FA Cup First Qualifying Round |
| 7 | Sat 12 Oct 2019 | 42-1 v Bracknell TownHaywards Heath Town 2-1 Bracknell Town | Buildbase FA Trophy Preliminary Round |
| 8 | Sat 19 Oct 2019 | 4 1-1 v Hastings UnitedHaywards Heath Town 1-1 Hastings United | BetVictor Isthmian South East Division |
| 9 | Tue 22 Oct 2019 | 110-1 v Hastings UnitedHastings United 1-0 Haywards Heath Town | Velocity Trophy Group 4 |
| 10 | Sat 30 Nov 2019 | 8 2-2 v VCD AthleticVCD Athletic 2-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 11 | Sat 7 Dec 2019 | 41-0 v Ashford UnitedHaywards Heath Town 1-0 Ashford United | BetVictor Isthmian South East Division |
| 12 | Sat 14 Dec 2019 | 4 0-0 v Herne BayHerne Bay 0-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 13 | Sat 21 Dec 2019 | 120-2 v WhyteleafeWhyteleafe 2-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 14 | Sat 28 Dec 2019 | 4 2-2 v WhitehawkHaywards Heath Town 2-2 Whitehawk | BetVictor Isthmian South East Division |
| 15 | Sat 4 Jan 2020 | 43-1 v Three BridgesThree Bridges 1-3 Haywards Heath Town | BetVictor Isthmian South East Division |
| 16 | Sat 11 Jan 2020 | 14 3-1 v Cray Valley PMHaywards Heath Town 3-1 Cray Valley PM | BetVictor Isthmian South East Division |
| 17 | Sat 18 Jan 2020 | 40-1 v Hastings UnitedHastings United 1-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 18 | Tue 21 Jan 2020 | 40-1 v Phoenix SportsPhoenix Sports 1-0 Haywards Heath Town | BetVictor Isthmian South East Division |
| 19 | Sat 25 Jan 2020 | 40-3 v Hythe TownHaywards Heath Town 0-3 Hythe Town | BetVictor Isthmian South East Division |
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