| 1 | 10/8/2019 | 230-0 v KingstonianKingstonian 0-0 Cray Wanderers | BetVictor Isthmian Premier Division |
| 2 | 14/8/2019 | 232-3 v Folkestone InvictaCray Wanderers 2-3 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 3 | 17/8/2019 | 230-0 v Corinthian-CasualsCray Wanderers 0-0 Corinthian-Casuals | BetVictor Isthmian Premier Division |
| 4 | 21/8/2019 | 13-2 v MargateCray Wanderers 3-2 Margate | BetVictor Isthmian Premier Division |
| 5 | 25/8/2019 | 15-0 v Hythe TownCray Wanderers 5-0 Hythe Town | Emirates FA Cup Preliminary Round |
| 6 | 31/8/2019 | 11-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 7 | 8/9/2019 | 12-1 v Bedfont SportsCray Wanderers 2-1 Bedfont Sports | Emirates FA Cup First Qualifying Round |
| 8 | 14/9/2019 | 11-1 v Haringey BoroughCray Wanderers 1-1 Haringey Borough | BetVictor Isthmian Premier Division |
| 9 | 17/9/2019 | 15-1 v Bishop's StortfordBishop's Stortford 1-5 Cray Wanderers | BetVictor Isthmian Premier Division |
| 10 | 22/9/2019 | 15-2 v Soham Town RangersCray Wanderers 5-2 Soham Town Rangers | Emirates FA Cup Second Qualifying Round |
| 11 | 28/9/2019 | 11-1 v East Thurrock UnitedCray Wanderers 1-1 East Thurrock United | BetVictor Isthmian Premier Division |
| 12 | 2/10/2019 | 1 3-1 v Bowers & PitseaCray Wanderers 3-1 Bowers & Pitsea | BetVictor Isthmian Premier Division |
| 13 | 5/10/2019 | 1 0-1 v Haringey BoroughHaringey Borough 1-0 Cray Wanderers | Emirates FA Cup Third Qualifying Round |
| 14 | 12/10/2019 | 13-5 v Enfield TownCray Wanderers 3-5 Enfield Town | BetVictor Isthmian Premier Division |
| 15 | 15/10/2019 | 12-1 v MersthamMerstham 1-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 16 | 19/10/2019 | 13-2 v LewesLewes 2-3 Cray Wanderers | BetVictor Isthmian Premier Division |
| 17 | 22/10/2019 | 11-1 v HorshamHorsham 1-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 18 | 26/10/2019 | 10-3 v Maldon & TiptreeMaldon & Tiptree 3-0 Cray Wanderers | Buildbase FA Trophy First Qualifying Round |
| 19 | 30/10/2019 | 10-2 v VCD AthleticCray Wanderers 0-2 VCD Athletic | Kent Senior Cup First Round |
| 20 | 2/11/2019 | 12-2 v WorthingCray Wanderers 2-2 Worthing | BetVictor Isthmian Premier Division |
| 21 | 9/11/2019 | 16-1 v CheshuntCray Wanderers 6-1 Cheshunt | BetVictor Isthmian Premier Division |
| 22 | 12/11/2019 | 11-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 23 | 16/11/2019 | 12-0 v Brightlingsea RegentBrightlingsea Regent 0-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 24 | 30/11/2019 | 10-4 v Carshalton AthleticCarshalton Athletic 4-0 Cray Wanderers | BetVictor Isthmian Premier Division |
| 25 | 7/12/2019 | 14-0 v Potters Bar TownCray Wanderers 4-0 Potters Bar Town | BetVictor Isthmian Premier Division |
| 26 | 14/12/2019 | 12-7 v Bognor Regis TownBognor Regis Town 7-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 27 | 21/12/2019 | 12-3 v WorthingWorthing 3-2 Cray Wanderers | Velocity Trophy |
| 28 | 26/12/2019 | 10-1 v LeatherheadCray Wanderers 0-1 Leatherhead | BetVictor Isthmian Premier Division |
| 29 | 1/1/2020 | 14-3 v MargateMargate 3-4 Cray Wanderers | BetVictor Isthmian Premier Division |
| 30 | 4/1/2020 | 10-0 v Wingate & FinchleyCray Wanderers 0-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 31 | 11/1/2020 | 12-1 v Bowers & PitseaBowers & Pitsea 1-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 32 | 15/1/2020 | 11-1 v HornchurchCray Wanderers 1-1 Hornchurch | BetVictor Isthmian Premier Division |
| 33 | 18/1/2020 | 1 2-1 v LewesCray Wanderers 2-1 Lewes | BetVictor Isthmian Premier Division |
| 34 | 25/1/2020 | 13-2 v Enfield TownEnfield Town 2-3 Cray Wanderers | BetVictor Isthmian Premier Division |
| 35 | 1/2/2020 | 12-1 v HorshamCray Wanderers 2-1 Horsham | BetVictor Isthmian Premier Division |
| 36 | 8/2/2020 | 12-1 v WorthingWorthing 1-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 37 | 15/2/2020 | 10-0 v KingstonianCray Wanderers 0-0 Kingstonian | BetVictor Isthmian Premier Division |
| 38 | 22/2/2020 | 1 1-0 v East Thurrock UnitedEast Thurrock United 0-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 39 | 1/3/2020 | 13-1 v MersthamCray Wanderers 3-1 Merstham | BetVictor Isthmian Premier Division |
| 40 | 7/3/2020 | 11-0 v Brightlingsea RegentCray Wanderers 1-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
