| 1 | Sat 17 Aug 2019 | 10-0 v Hastings UnitedCray Valley PM 0-0 Hastings United |
| 2 | Tue 20 Aug 2019 | 13-1 v SittingbourneSittingbourne 1-3 Cray Valley PM |
| 3 | Mon 26 Aug 2019 | 11-0 v Sevenoaks TownCray Valley PM 1-0 Sevenoaks Town |
| 4 | Sat 31 Aug 2019 | 13-0 v Herne BayHerne Bay 0-3 Cray Valley PM |
| 5 | Sat 14 Sep 2019 | 1 0-2 v Chichester CityCray Valley PM 0-2 Chichester City |
| 6 | Tue 17 Sep 2019 | 11-1 v Whitstable TownWhitstable Town 1-1 Cray Valley PM |
| 7 | Sat 5 Oct 2019 | 12-1 v Ashford UnitedAshford United 1-2 Cray Valley PM |
| 8 | Sat 19 Oct 2019 | 12-0 v Faversham TownCray Valley PM 2-0 Faversham Town |
| 9 | Sat 26 Oct 2019 | 13-2 v Burgess Hill TownBurgess Hill Town 2-3 Cray Valley PM |
| 10 | Sat 2 Nov 2019 | 11-0 v Three BridgesCray Valley PM 1-0 Three Bridges |
| 11 | Sat 9 Nov 2019 | 12-0 v RamsgateRamsgate 0-2 Cray Valley PM |
| 12 | Sat 16 Nov 2019 | 11-1 v Hythe TownCray Valley PM 1-1 Hythe Town |
| 13 | Sat 23 Nov 2019 | 11-1 v GuernseyCray Valley PM 1-1 Guernsey |
| 14 | Sat 30 Nov 2019 | 10-2 v WhitehawkWhitehawk 2-0 Cray Valley PM |
| 15 | Sat 7 Dec 2019 | 13-1 v East Grinstead TownCray Valley PM 3-1 East Grinstead Town |
| 16 | Sat 14 Dec 2019 | 10-2 v Phoenix SportsPhoenix Sports 2-0 Cray Valley PM |
| 17 | Wed 1 Jan 2020 | 11-1 v Sevenoaks TownSevenoaks Town 1-1 Cray Valley PM |
| 18 | Sat 4 Jan 2020 | 11-2 v Herne BayCray Valley PM 1-2 Herne Bay |
| 19 | Sat 11 Jan 2020 | 11-3 v Haywards Heath TownHaywards Heath Town 3-1 Cray Valley PM |
| 20 | Sat 18 Jan 2020 | 10-0 v Faversham TownFaversham Town 0-0 Cray Valley PM |
| 21 | Sat 25 Jan 2020 | 13-1 v Ashford UnitedCray Valley PM 3-1 Ashford United |
| 22 | Tue 28 Jan 2020 | 15-0 v VCD AthleticCray Valley PM 5-0 VCD Athletic |
| 23 | Sat 1 Feb 2020 | 14-0 v WhyteleafeWhyteleafe 0-4 Cray Valley PM |
| 24 | Tue 4 Feb 2020 | 14-3 v Whitstable TownCray Valley PM 4-3 Whitstable Town |
| 25 | Sat 8 Feb 2020 | 12-0 v Phoenix SportsCray Valley PM 2-0 Phoenix Sports |
| 26 | Sat 22 Feb 2020 | 11-0 v Burgess Hill TownCray Valley PM 1-0 Burgess Hill Town |
| 27 | Sat 7 Mar 2020 | 15-3 v RamsgateCray Valley PM 5-3 Ramsgate |
| 28 | Tue 10 Mar 2020 | 13-2 v WhyteleafeCray Valley PM 3-2 Whyteleafe |
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