| 1 | Sat 17 Aug 2019 | 122-1 v East Grinstead TownEast Grinstead Town 1-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 2 | Tue 20 Aug 2019 | 105-1 v Burgess Hill TownHaywards Heath Town 5-1 Burgess Hill Town | BetVictor Isthmian South East Division |
| 3 | Sat 24 Aug 2019 | 102-1 v Tunbridge WellsHaywards Heath Town 2-1 Tunbridge Wells | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 101-1 v WhitehawkWhitehawk 1-1 Haywards Heath Town | BetVictor Isthmian South East Division |
| 5 | Sat 31 Aug 2019 | 10 0-2 v Three BridgesHaywards Heath Town 0-2 Three Bridges | BetVictor Isthmian South East Division |
| 6 | Tue 3 Sep 2019 | 10 0-2 v Burgess Hill TownBurgess Hill Town 2-0 Haywards Heath Town | Velocity Trophy Group 4 |
| 7 | Sat 7 Sep 2019 | 120-1 v Hayes & Yeading UnitedHaywards Heath Town 0-1 Hayes & Yeading United | Emirates FA Cup First Qualifying Round |
| 8 | Sat 14 Sep 2019 | 141-1 v Whitstable TownWhitstable Town 1-1 Haywards Heath Town | BetVictor Isthmian South East Division |
| 9 | Tue 17 Sep 2019 | 111-1 v GuernseyHaywards Heath Town 1-1 Guernsey | BetVictor Isthmian South East Division |
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