| 1 | 11/8/2018 | 13-0 v Greenwich BoroughGreenwich Borough 0-3 Cray Wanderers | Bostik League South East Division |
| 2 | 19/8/2018 | 12-0 v Whitstable TownCray Wanderers 2-0 Whitstable Town | Bostik League South East Division |
| 3 | 25/8/2018 | 11-1 v RusthallCray Wanderers 1-1 Rusthall | Emirates FA Cup Preliminary Round |
| 4 | 27/8/2018 | 12-0 v SittingbourneSittingbourne 0-2 Cray Wanderers | Bostik League South East Division |
| 5 | 1/9/2018 | 12-0 v East Grinstead TownCray Wanderers 2-0 East Grinstead Town | Bostik League South East Division |
| 6 | 5/9/2018 | 12-2 v RusthallRusthall 2-2 Cray Wanderers | Emirates FA Cup Preliminary Round |
| 7 | 8/9/2018 | 12-3 v Metropolitan PoliceMetropolitan Police 3-2 Cray Wanderers | Emirates FA Cup First Qualifying Round |
| 8 | 15/9/2018 | 13-1 v Ashford UnitedAshford United 1-3 Cray Wanderers | Bostik League South East Division |
| 9 | 22/9/2018 | 14-3 v Hythe TownCray Wanderers 4-3 Hythe Town | Bostik League South East Division |
| 10 | 26/9/2018 | 11-1 v WhyteleafeCray Wanderers 1-1 Whyteleafe | Bostik League South East Division |
| 11 | 29/9/2018 | 1 2-1 v VCD AthleticVCD Athletic 1-2 Cray Wanderers | Bostik League South East Division |
| 12 | 6/10/2018 | 17-2 v Faversham TownCray Wanderers 7-2 Faversham Town | Bostik League South East Division |
| 13 | 13/10/2018 | 10-2 v Canvey IslandCanvey Island 2-0 Cray Wanderers | Buildbase FA Trophy Preliminary Round |
| 14 | 20/10/2018 | 12-1 v Herne BayHerne Bay 1-2 Cray Wanderers | Bostik League South East Division |
| 15 | 3/11/2018 | 11-0 v Haywards Heath TownHaywards Heath Town 0-1 Cray Wanderers | Bostik League South East Division |
| 16 | 11/11/2018 | 12-1 v Hastings UnitedCray Wanderers 2-1 Hastings United | Bostik League South East Division |
| 17 | 14/11/2018 | 11-5 v Charlton AthleticCray Wanderers 1-5 Charlton Athletic | Kent Senior Cup Second Round |
| 18 | 17/11/2018 | 12-1 v GuernseyGuernsey 1-2 Cray Wanderers | Bostik League South East Division |
| 19 | 25/11/2018 | 10-0 v RamsgateCray Wanderers 0-0 Ramsgate | Bostik League South East Division |
| 20 | 15/12/2018 | 12-4 v HorshamHorsham 4-2 Cray Wanderers | Bostik League South East Division |
| 21 | 23/12/2018 | 12-1 v SittingbourneCray Wanderers 2-1 Sittingbourne | Bostik League South East Division |
| 22 | 29/12/2018 | 11-0 v Sevenoaks TownSevenoaks Town 0-1 Cray Wanderers | Bostik League South East Division |
| 23 | 6/1/2019 | 11-0 v Three BridgesCray Wanderers 1-0 Three Bridges | Bostik League South East Division |
| 24 | 12/1/2019 | 12-0 v East Grinstead TownEast Grinstead Town 0-2 Cray Wanderers | Bostik League South East Division |
| 25 | 19/1/2019 | 13-1 v VCD AthleticCray Wanderers 3-1 VCD Athletic | Bostik League South East Division |
| 26 | 26/1/2019 | 11-1 v Faversham TownFaversham Town 1-1 Cray Wanderers | Bostik League South East Division |
| 27 | 2/2/2019 | 16-0 v Herne BayCray Wanderers 6-0 Herne Bay | Bostik League South East Division |
| 28 | 5/2/2019 | 13-1 v WhyteleafeWhyteleafe 1-3 Cray Wanderers | Bostik League South East Division |
| 29 | 9/2/2019 | 13-0 v GuernseyCray Wanderers 3-0 Guernsey | Bostik League South East Division |
| 30 | 16/2/2019 | 12-2 v RamsgateRamsgate 2-2 Cray Wanderers | Bostik League South East Division |
| 31 | 2/3/2019 | 11-0 v Phoenix SportsPhoenix Sports 0-1 Cray Wanderers | Bostik League South East Division |
| 32 | 9/3/2019 | 12-0 v HorshamCray Wanderers 2-0 Horsham | Bostik League South East Division |
| 33 | 16/3/2019 | 12-3 v Hastings UnitedHastings United 3-2 Cray Wanderers | Bostik League South East Division |
| 34 | 23/3/2019 | 12-2 v Haywards Heath TownCray Wanderers 2-2 Haywards Heath Town | Bostik League South East Division |
| 35 | 30/3/2019 | 10-1 v Whitstable TownWhitstable Town 1-0 Cray Wanderers | Bostik League South East Division |
| 36 | 7/4/2019 | 11-1 v Greenwich BoroughCray Wanderers 1-1 Greenwich Borough | Bostik League South East Division |
| 37 | 13/4/2019 | 13-1 v Ashford UnitedCray Wanderers 3-1 Ashford United | Bostik League South East Division |
| 38 | 20/4/2019 | 12-0 v Three BridgesThree Bridges 0-2 Cray Wanderers | Bostik League South East Division |
| 39 | 22/4/2019 | 13-4 v Sevenoaks TownCray Wanderers 3-4 Sevenoaks Town | Bostik League South East Division |
| 40 | 27/4/2019 | 13-1 v Hythe TownHythe Town 1-3 Cray Wanderers | Bostik League South East Division |
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