| 1 | Sat 10 Aug 2019 | 230-0 v KingstonianKingstonian 0-0 Cray Wanderers |
| 2 | Wed 14 Aug 2019 | 232-3 v Folkestone InvictaCray Wanderers 2-3 Folkestone Invicta |
| 3 | Sat 17 Aug 2019 | 230-0 v Corinthian-CasualsCray Wanderers 0-0 Corinthian-Casuals |
| 4 | Wed 21 Aug 2019 | 13-2 v MargateCray Wanderers 3-2 Margate |
| 5 | Sat 31 Aug 2019 | 11-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers |
| 6 | Sat 14 Sep 2019 | 11-1 v Haringey BoroughCray Wanderers 1-1 Haringey Borough |
| 7 | Tue 17 Sep 2019 | 15-1 v Bishop's StortfordBishop's Stortford 1-5 Cray Wanderers |
| 8 | Sat 28 Sep 2019 | 11-1 v East Thurrock UnitedCray Wanderers 1-1 East Thurrock United |
| 9 | Wed 2 Oct 2019 | 1 3-1 v Bowers & PitseaCray Wanderers 3-1 Bowers & Pitsea |
| 10 | Sat 12 Oct 2019 | 13-5 v Enfield TownCray Wanderers 3-5 Enfield Town |
| 11 | Tue 15 Oct 2019 | 12-1 v MersthamMerstham 1-2 Cray Wanderers |
| 12 | Sat 19 Oct 2019 | 13-2 v LewesLewes 2-3 Cray Wanderers |
| 13 | Tue 22 Oct 2019 | 11-1 v HorshamHorsham 1-1 Cray Wanderers |
| 14 | Sat 2 Nov 2019 | 12-2 v WorthingCray Wanderers 2-2 Worthing |
| 15 | Sat 9 Nov 2019 | 16-1 v CheshuntCray Wanderers 6-1 Cheshunt |
| 16 | Tue 12 Nov 2019 | 11-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers |
| 17 | Sat 16 Nov 2019 | 12-0 v Brightlingsea RegentBrightlingsea Regent 0-2 Cray Wanderers |
| 18 | Sat 30 Nov 2019 | 10-4 v Carshalton AthleticCarshalton Athletic 4-0 Cray Wanderers |
| 19 | Sat 7 Dec 2019 | 14-0 v Potters Bar TownCray Wanderers 4-0 Potters Bar Town |
| 20 | Sat 14 Dec 2019 | 12-7 v Bognor Regis TownBognor Regis Town 7-2 Cray Wanderers |
| 21 | Thu 26 Dec 2019 | 10-1 v LeatherheadCray Wanderers 0-1 Leatherhead |
| 22 | Wed 1 Jan 2020 | 14-3 v MargateMargate 3-4 Cray Wanderers |
| 23 | Sat 4 Jan 2020 | 10-0 v Wingate & FinchleyCray Wanderers 0-0 Wingate & Finchley |
| 24 | Sat 11 Jan 2020 | 12-1 v Bowers & PitseaBowers & Pitsea 1-2 Cray Wanderers |
| 25 | Wed 15 Jan 2020 | 11-1 v HornchurchCray Wanderers 1-1 Hornchurch |
| 26 | Sat 18 Jan 2020 | 1 2-1 v LewesCray Wanderers 2-1 Lewes |
| 27 | Sat 25 Jan 2020 | 13-2 v Enfield TownEnfield Town 2-3 Cray Wanderers |
| 28 | Sat 1 Feb 2020 | 12-1 v HorshamCray Wanderers 2-1 Horsham |
| 29 | Sat 8 Feb 2020 | 12-1 v WorthingWorthing 1-2 Cray Wanderers |
| 30 | Sat 15 Feb 2020 | 10-0 v KingstonianCray Wanderers 0-0 Kingstonian |
| 31 | Sat 22 Feb 2020 | 1 1-0 v East Thurrock UnitedEast Thurrock United 0-1 Cray Wanderers |
| 32 | Sun 1 Mar 2020 | 13-1 v MersthamCray Wanderers 3-1 Merstham |
| 33 | Sat 7 Mar 2020 | 11-0 v Brightlingsea RegentCray Wanderers 1-0 Brightlingsea Regent |
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