| 1 | 11/8/2018 | 12-2 v Deal TownDeal Town 2-2 Whitstable Town | Emirates FA Cup Extra Preliminary Round |
| 2 | 15/8/2018 | 14-3 v Deal TownWhitstable Town 4-3 Deal Town | Emirates FA Cup Extra Preliminary Round |
| 3 | 19/8/2018 | 10-2 v Cray WanderersCray Wanderers 2-0 Whitstable Town | Bostik League South East Division |
| 4 | 25/8/2018 | 12-0 v Hounslow UnitedHounslow United 0-2 Whitstable Town | Emirates FA Cup Preliminary Round |
| 5 | 27/8/2018 | 11-4 v RamsgateRamsgate 4-1 Whitstable Town | Bostik League South East Division |
| 6 | 1/9/2018 | 11-0 v Ashford UnitedWhitstable Town 1-0 Ashford United | Bostik League South East Division |
| 7 | 8/9/2018 | 10-5 v Bognor Regis TownWhitstable Town 0-5 Bognor Regis Town | Emirates FA Cup First Qualifying Round |
| 8 | 15/9/2018 | 12-0 v Phoenix SportsPhoenix Sports 0-2 Whitstable Town | Bostik League South East Division |
| 9 | 18/9/2018 | 10-0 v Haywards Heath TownWhitstable Town 0-0 Haywards Heath Town | Bostik League South East Division |
| 10 | 22/9/2018 | 11-1 v Three BridgesWhitstable Town 1-1 Three Bridges | Bostik League South East Division |
| 11 | 25/9/2018 | 11-1 v Sevenoaks TownWhitstable Town 1-1 Sevenoaks Town | Bostik League South East Division |
| 12 | 29/9/2018 | 12-1 v Faversham TownFaversham Town 1-2 Whitstable Town | Bostik League South East Division |
| 13 | 6/10/2018 | 12-0 v Greenwich BoroughWhitstable Town 2-0 Greenwich Borough | Bostik League South East Division |
| 14 | 9/10/2018 | 12-0 v RamsgateRamsgate 0-2 Whitstable Town | Velocity Trophy First Round |
| 15 | 13/10/2018 | 14-1 v Bedfont SportsBedfont Sports 1-4 Whitstable Town | Buildbase FA Trophy Preliminary Round |
| 16 | 20/10/2018 | 11-3 v VCD AthleticVCD Athletic 3-1 Whitstable Town | Bostik League South East Division |
| 17 | 27/10/2018 | 11-3 v Brentwood TownBrentwood Town 3-1 Whitstable Town | Buildbase FA Trophy First Qualifying Round |
| 18 | 3/11/2018 | 10-2 v WhyteleafeWhitstable Town 0-2 Whyteleafe | Bostik League South East Division |
| 19 | 6/11/2018 | 14-1 v Greenwich BoroughWhitstable Town 4-1 Greenwich Borough | Velocity Trophy Second Round |
| 20 | 10/11/2018 | 12-1 v SittingbourneSittingbourne 1-2 Whitstable Town | Bostik League South East Division |
| 21 | 13/11/2018 | 14-3 v CheshuntWhitstable Town 4-3 Cheshunt | Velocity Trophy Third Round |
| 22 | 17/11/2018 | 11-3 v Hastings UnitedHastings United 3-1 Whitstable Town | Bostik League South East Division |
| 23 | 1/12/2018 | 10-4 v HorshamHorsham 4-0 Whitstable Town | Bostik League South East Division |
| 24 | 8/12/2018 | 10-4 v Herne BayWhitstable Town 0-4 Herne Bay | Bostik League South East Division |
| 25 | 15/12/2018 | 11-1 v GuernseyGuernsey 1-1 Whitstable Town | Bostik League South East Division |
| 26 | 26/12/2018 | 11-0 v RamsgateWhitstable Town 1-0 Ramsgate | Bostik League South East Division |
| 27 | 29/12/2018 | 10-2 v Hythe TownHythe Town 2-0 Whitstable Town | Bostik League South East Division |
| 28 | 5/1/2019 | 11-1 v East Grinstead TownWhitstable Town 1-1 East Grinstead Town | Bostik League South East Division |
| 29 | 12/1/2019 | 10-2 v Ashford UnitedAshford United 2-0 Whitstable Town | Bostik League South East Division |
| 30 | 15/1/2019 | 11-4 v AFC HornchurchAFC Hornchurch 4-1 Whitstable Town | Velocity Trophy Quarter Final |
| 31 | 19/1/2019 | 11-2 v Faversham TownWhitstable Town 1-2 Faversham Town | Bostik League South East Division |
| 32 | 26/1/2019 | 10-0 v Greenwich BoroughGreenwich Borough 0-0 Whitstable Town | Bostik League South East Division |
| 33 | 5/2/2019 | 11-1 v Sevenoaks TownSevenoaks Town 1-1 Whitstable Town | Bostik League South East Division |
| 34 | 9/2/2019 | 11-1 v Hastings UnitedWhitstable Town 1-1 Hastings United | Bostik League South East Division |
| 35 | 23/2/2019 | 10-3 v HorshamWhitstable Town 0-3 Horsham | Bostik League South East Division |
| 36 | 2/3/2019 | 11-3 v Herne BayHerne Bay 3-1 Whitstable Town | Bostik League South East Division |
| 37 | 9/3/2019 | 13-1 v GuernseyWhitstable Town 3-1 Guernsey | Bostik League South East Division |
| 38 | 16/3/2019 | 12-1 v SittingbourneWhitstable Town 2-1 Sittingbourne | Bostik League South East Division |
| 39 | 19/3/2019 | 14-1 v VCD AthleticWhitstable Town 4-1 VCD Athletic | Bostik League South East Division |
| 40 | 23/3/2019 | 11-1 v WhyteleafeWhyteleafe 1-1 Whitstable Town | Bostik League South East Division |
| 41 | 30/3/2019 | 11-0 v Cray WanderersWhitstable Town 1-0 Cray Wanderers | Bostik League South East Division |
| 42 | 6/4/2019 | 11-2 v Haywards Heath TownHaywards Heath Town 2-1 Whitstable Town | Bostik League South East Division |
| 43 | 13/4/2019 | 12-1 v Phoenix SportsWhitstable Town 2-1 Phoenix Sports | Bostik League South East Division |
| 44 | 20/4/2019 | 10-4 v East Grinstead TownEast Grinstead Town 4-0 Whitstable Town | Bostik League South East Division |
| 45 | 22/4/2019 | 10-0 v Hythe TownWhitstable Town 0-0 Hythe Town | Bostik League South East Division |
| 46 | 27/4/2019 | 11-2 v Three BridgesThree Bridges 2-1 Whitstable Town | Bostik League South East Division |
