| 1 | 10/8/2019 | 20-0 v KingstonianKingstonian 0-0 Cray Wanderers | BetVictor Isthmian Premier Division |
| 2 | 14/8/2019 | 22-3 v Folkestone InvictaCray Wanderers 2-3 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 3 | 17/8/2019 | 20-0 v Corinthian-CasualsCray Wanderers 0-0 Corinthian-Casuals | BetVictor Isthmian Premier Division |
| 4 | 21/8/2019 | 23-2 v MargateCray Wanderers 3-2 Margate | BetVictor Isthmian Premier Division |
| 5 | 25/8/2019 | 25-0 v Hythe TownCray Wanderers 5-0 Hythe Town | Emirates FA Cup Preliminary Round |
| 6 | 31/8/2019 | 21-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 7 | 8/9/2019 | 22-1 v Bedfont SportsCray Wanderers 2-1 Bedfont Sports | Emirates FA Cup First Qualifying Round |
| 8 | 14/9/2019 | 21-1 v Haringey BoroughCray Wanderers 1-1 Haringey Borough | BetVictor Isthmian Premier Division |
| 9 | 17/9/2019 | 25-1 v Bishop's StortfordBishop's Stortford 1-5 Cray Wanderers | BetVictor Isthmian Premier Division |
| 10 | 22/9/2019 | 25-2 v Soham Town RangersCray Wanderers 5-2 Soham Town Rangers | Emirates FA Cup Second Qualifying Round |
| 11 | 28/9/2019 | 21-1 v East Thurrock UnitedCray Wanderers 1-1 East Thurrock United | BetVictor Isthmian Premier Division |
| 12 | 2/10/2019 | 2 3-1 v Bowers & PitseaCray Wanderers 3-1 Bowers & Pitsea | BetVictor Isthmian Premier Division |
| 13 | 5/10/2019 | 20-1 v Haringey BoroughHaringey Borough 1-0 Cray Wanderers | Emirates FA Cup Third Qualifying Round |
| 14 | 15/10/2019 | 22-1 v MersthamMerstham 1-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 15 | 19/10/2019 | 23-2 v LewesLewes 2-3 Cray Wanderers | BetVictor Isthmian Premier Division |
| 16 | 22/10/2019 | 21-1 v HorshamHorsham 1-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 17 | 26/10/2019 | 20-3 v Maldon & TiptreeMaldon & Tiptree 3-0 Cray Wanderers | Buildbase FA Trophy First Qualifying Round |
| 18 | 30/10/2019 | 20-2 v VCD AthleticCray Wanderers 0-2 VCD Athletic | Kent Senior Cup First Round |
| 19 | 2/11/2019 | 2 2-2 v WorthingCray Wanderers 2-2 Worthing | BetVictor Isthmian Premier Division |
| 20 | 9/11/2019 | 26-1 v CheshuntCray Wanderers 6-1 Cheshunt | BetVictor Isthmian Premier Division |
| 21 | 12/11/2019 | 21-0 v Wingate & FinchleyWingate & Finchley 0-1 Cray Wanderers | BetVictor Isthmian Premier Division |
