| 1 | Sat 17 Aug 2019 | 12-2 v Herne BayWhyteleafe 2-2 Herne Bay |
| 2 | Tue 20 Aug 2019 | 13-2 v Chichester CityChichester City 2-3 Whyteleafe |
| 3 | Mon 26 Aug 2019 | 14-1 v GuernseyWhyteleafe 4-1 Guernsey |
| 4 | Sat 31 Aug 2019 | 10-1 v Hastings UnitedHastings United 1-0 Whyteleafe |
| 5 | Sat 26 Oct 2019 | 11-3 v RamsgateRamsgate 3-1 Whyteleafe |
| 6 | Tue 29 Oct 2019 | 14-3 v Burgess Hill TownWhyteleafe 4-3 Burgess Hill Town |
| 7 | Sat 2 Nov 2019 | 12-1 v Phoenix SportsWhyteleafe 2-1 Phoenix Sports |
| 8 | Sat 9 Nov 2019 | 12-2 v Hythe TownHythe Town 2-2 Whyteleafe |
| 9 | Tue 12 Nov 2019 | 13-4 v Ashford UnitedWhyteleafe 3-4 Ashford United |
| 10 | Sat 16 Nov 2019 | 10-0 v East Grinstead TownWhyteleafe 0-0 East Grinstead Town |
| 11 | Sat 23 Nov 2019 | 12-0 v Whitstable TownWhitstable Town 0-2 Whyteleafe |
| 12 | Sat 30 Nov 2019 | 13-1 v Three BridgesWhyteleafe 3-1 Three Bridges |
| 13 | Tue 3 Dec 2019 | 12-1 v SittingbourneWhyteleafe 2-1 Sittingbourne |
| 14 | Sat 7 Dec 2019 | 10-0 v Faversham TownFaversham Town 0-0 Whyteleafe |
| 15 | Sat 14 Dec 2019 | 11-1 v Sevenoaks TownWhyteleafe 1-1 Sevenoaks Town |
| 16 | Sat 21 Dec 2019 | 12-0 v Haywards Heath TownWhyteleafe 2-0 Haywards Heath Town |
| 17 | Sat 28 Dec 2019 | 10-0 v GuernseyGuernsey 0-0 Whyteleafe |
| 18 | Sat 4 Jan 2020 | 10-1 v Hastings UnitedWhyteleafe 0-1 Hastings United |
| 19 | Sat 11 Jan 2020 | 11-2 v VCD AthleticVCD Athletic 2-1 Whyteleafe |
| 20 | Sat 18 Jan 2020 | 14-2 v WhitehawkWhyteleafe 4-2 Whitehawk |
| 21 | Sat 25 Jan 2020 | 11-0 v SittingbourneSittingbourne 0-1 Whyteleafe |
| 22 | Tue 28 Jan 2020 | 10-1 v WhitehawkWhitehawk 1-0 Whyteleafe |
| 23 | Sat 1 Feb 2020 | 10-4 v Cray Valley PMWhyteleafe 0-4 Cray Valley PM |
| 24 | Sat 8 Feb 2020 | 1 2-0 v Sevenoaks TownSevenoaks Town 0-2 Whyteleafe |
| 25 | Sat 15 Feb 2020 | 13-1 v Faversham TownWhyteleafe 3-1 Faversham Town |
| 26 | Sat 22 Feb 2020 | 13-2 v RamsgateWhyteleafe 3-2 Ramsgate |
| 27 | Sat 7 Mar 2020 | 10-2 v Hythe TownWhyteleafe 0-2 Hythe Town |
| 28 | Tue 10 Mar 2020 | 12-3 v Cray Valley PMCray Valley PM 3-2 Whyteleafe |
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