| 1 | 10/8/2019 | 100-0 v KingstonianKingstonian 0-0 Cray Wanderers | BetVictor Isthmian Premier Division |
| 2 | 14/8/2019 | 10 2-3 v Folkestone InvictaCray Wanderers 2-3 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 3 | 17/8/2019 | 100-0 v Corinthian-CasualsCray Wanderers 0-0 Corinthian-Casuals | BetVictor Isthmian Premier Division |
| 4 | 21/8/2019 | 10 3-2 v MargateCray Wanderers 3-2 Margate | BetVictor Isthmian Premier Division |
| 5 | 25/8/2019 | 105-0 v Hythe TownCray Wanderers 5-0 Hythe Town | Emirates FA Cup Preliminary Round |
| 6 | 31/8/2019 | 101-1 v Potters Bar TownPotters Bar Town 1-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 7 | 8/9/2019 | 102-1 v Bedfont SportsCray Wanderers 2-1 Bedfont Sports | Emirates FA Cup First Qualifying Round |
| 8 | 14/9/2019 | 101-1 v Haringey BoroughCray Wanderers 1-1 Haringey Borough | BetVictor Isthmian Premier Division |
| 9 | 17/9/2019 | 105-1 v Bishop's StortfordBishop's Stortford 1-5 Cray Wanderers | BetVictor Isthmian Premier Division |
| 10 | 22/9/2019 | 105-2 v Soham Town RangersCray Wanderers 5-2 Soham Town Rangers | Emirates FA Cup Second Qualifying Round |
| 11 | 28/9/2019 | 101-1 v East Thurrock UnitedCray Wanderers 1-1 East Thurrock United | BetVictor Isthmian Premier Division |
| 12 | 2/10/2019 | 103-1 v Bowers & PitseaCray Wanderers 3-1 Bowers & Pitsea | BetVictor Isthmian Premier Division |
| 13 | 5/10/2019 | 100-1 v Haringey BoroughHaringey Borough 1-0 Cray Wanderers | Emirates FA Cup Third Qualifying Round |
| 14 | 12/10/2019 | 103-5 v Enfield TownCray Wanderers 3-5 Enfield Town | BetVictor Isthmian Premier Division |
| 15 | 15/10/2019 | 102-1 v MersthamMerstham 1-2 Cray Wanderers | BetVictor Isthmian Premier Division |
