| 1 | 12/10/2019 | 43-5 v Enfield TownCray Wanderers 3-5 Enfield Town | Isthmian League Premier Division |
| 2 | 15/10/2019 | 42-1 v MersthamMerstham 1-2 Cray Wanderers | Isthmian League Premier Division |
| 3 | 19/10/2019 | 43-2 v LewesLewes 2-3 Cray Wanderers | Isthmian League Premier Division |
| 4 | 22/10/2019 | 41-1 v HorshamHorsham 1-1 Cray Wanderers | Isthmian League Premier Division |
| 5 | 26/10/2019 | 40-3 v Maldon & TiptreeMaldon & Tiptree 3-0 Cray Wanderers | Buildbase FA Trophy First Qualifying Round |
| 6 | 2/11/2019 | 42-2 v WorthingCray Wanderers 2-2 Worthing | Isthmian League Premier Division |
| 7 | 9/11/2019 | 46-1 v CheshuntCray Wanderers 6-1 Cheshunt | Isthmian League Premier Division |
| 8 | 12/11/2019 | 41-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers | Isthmian League Premier Division |
| 9 | 16/11/2019 | 42-0 v Brightlingsea RegentBrightlingsea Regent 0-2 Cray Wanderers | Isthmian League Premier Division |
| 10 | 30/11/2019 | 40-4 v Carshalton AthleticCarshalton Athletic 4-0 Cray Wanderers | Isthmian League Premier Division |
| 11 | 7/12/2019 | 44-0 v Potters Bar TownCray Wanderers 4-0 Potters Bar Town | Isthmian League Premier Division |
| 12 | 14/12/2019 | 4 2-7 v Bognor Regis TownBognor Regis Town 7-2 Cray Wanderers | Isthmian League Premier Division |
| 13 | 21/12/2019 | 42-3 v WorthingWorthing 3-2 Cray Wanderers | Velocity Trophy |
| 14 | 26/12/2019 | 40-1 v LeatherheadCray Wanderers 0-1 Leatherhead | Isthmian League Premier Division |
| 15 | 1/1/2020 | 44-3 v MargateMargate 3-4 Cray Wanderers | Isthmian League Premier Division |
| 16 | 4/1/2020 | 40-0 v Wingate & FinchleyCray Wanderers 0-0 Wingate & Finchley | Isthmian League Premier Division |
| 17 | 11/1/2020 | 42-1 v Bowers & PitseaBowers & Pitsea 1-2 Cray Wanderers | Isthmian League Premier Division |
| 18 | 15/1/2020 | 41-1 v HornchurchCray Wanderers 1-1 Hornchurch | Isthmian League Premier Division |
| 19 | 18/1/2020 | 42-1 v LewesCray Wanderers 2-1 Lewes | Isthmian League Premier Division |
| 20 | 25/1/2020 | 43-2 v Enfield TownEnfield Town 2-3 Cray Wanderers | Isthmian League Premier Division |
| 21 | 1/2/2020 | 42-1 v HorshamCray Wanderers 2-1 Horsham | Isthmian League Premier Division |
| 22 | 8/2/2020 | 42-1 v WorthingWorthing 1-2 Cray Wanderers | Isthmian League Premier Division |
| 23 | 1/3/2020 | 43-1 v MersthamCray Wanderers 3-1 Merstham | Isthmian League Premier Division |
| 24 | 7/3/2020 | 41-0 v Brightlingsea RegentCray Wanderers 1-0 Brightlingsea Regent | Isthmian League Premier Division |
