| 1 | 11/8/2018 | 8 3-0 v Greenwich BoroughGreenwich Borough 0-3 Cray Wanderers | Bostik League South East Division |
| 2 | 19/8/2018 | 82-0 v Whitstable TownCray Wanderers 2-0 Whitstable Town | Bostik League South East Division |
| 3 | 25/8/2018 | 81-1 v RusthallCray Wanderers 1-1 Rusthall | Emirates FA Cup Preliminary Round |
| 4 | 27/8/2018 | 82-0 v SittingbourneSittingbourne 0-2 Cray Wanderers | Bostik League South East Division |
| 5 | 1/9/2018 | 82-0 v East Grinstead TownCray Wanderers 2-0 East Grinstead Town | Bostik League South East Division |
| 6 | 5/9/2018 | 82-2 v RusthallRusthall 2-2 Cray Wanderers | Emirates FA Cup Preliminary Round |
| 7 | 13/10/2018 | 140-2 v Canvey IslandCanvey Island 2-0 Cray Wanderers | Buildbase FA Trophy Preliminary Round |
| 8 | 3/11/2018 | 141-0 v Haywards Heath TownHaywards Heath Town 0-1 Cray Wanderers | Bostik League South East Division |
| 9 | 14/11/2018 | 81-5 v Charlton AthleticCray Wanderers 1-5 Charlton Athletic | Kent Senior Cup Second Round |
| 10 | 25/11/2018 | 150-0 v RamsgateCray Wanderers 0-0 Ramsgate | Bostik League South East Division |
| 11 | 15/12/2018 | 82-4 v HorshamHorsham 4-2 Cray Wanderers | Bostik League South East Division |
| 12 | 23/12/2018 | 82-1 v SittingbourneCray Wanderers 2-1 Sittingbourne | Bostik League South East Division |
| 13 | 29/12/2018 | 81-0 v Sevenoaks TownSevenoaks Town 0-1 Cray Wanderers | Bostik League South East Division |
| 14 | 6/1/2019 | 71-0 v Three BridgesCray Wanderers 1-0 Three Bridges | Bostik League South East Division |
| 15 | 12/1/2019 | 82-0 v East Grinstead TownEast Grinstead Town 0-2 Cray Wanderers | Bostik League South East Division |
| 16 | 19/1/2019 | 83-1 v VCD AthleticCray Wanderers 3-1 VCD Athletic | Bostik League South East Division |
| 17 | 26/1/2019 | 81-1 v Faversham TownFaversham Town 1-1 Cray Wanderers | Bostik League South East Division |
| 18 | 2/2/2019 | 8 6-0 v Herne BayCray Wanderers 6-0 Herne Bay | Bostik League South East Division |
| 19 | 5/2/2019 | 143-1 v WhyteleafeWhyteleafe 1-3 Cray Wanderers | Bostik League South East Division |
| 20 | 9/2/2019 | 83-0 v GuernseyCray Wanderers 3-0 Guernsey | Bostik League South East Division |
| 21 | 16/2/2019 | 152-2 v RamsgateRamsgate 2-2 Cray Wanderers | Bostik League South East Division |
| 22 | 2/3/2019 | 81-0 v Phoenix SportsPhoenix Sports 0-1 Cray Wanderers | Bostik League South East Division |
| 23 | 9/3/2019 | 82-0 v HorshamCray Wanderers 2-0 Horsham | Bostik League South East Division |
| 24 | 16/3/2019 | 82-3 v Hastings UnitedHastings United 3-2 Cray Wanderers | Bostik League South East Division |
| 25 | 23/3/2019 | 152-2 v Haywards Heath TownCray Wanderers 2-2 Haywards Heath Town | Bostik League South East Division |
| 26 | 30/3/2019 | 8 0-1 v Whitstable TownWhitstable Town 1-0 Cray Wanderers | Bostik League South East Division |
| 27 | 7/4/2019 | 81-1 v Greenwich BoroughCray Wanderers 1-1 Greenwich Borough | Bostik League South East Division |
| 28 | 13/4/2019 | 103-1 v Ashford UnitedCray Wanderers 3-1 Ashford United | Bostik League South East Division |
