| 1 | 11/8/2018 | 62-1 v HorshamHorsham 1-2 Sittingbourne | Bostik League South East Division |
| 2 | 18/8/2018 | 6 4-2 v Greenwich BoroughSittingbourne 4-2 Greenwich Borough | Bostik League South East Division |
| 3 | 25/8/2018 | 62-0 v BearstedSittingbourne 2-0 Bearsted | Emirates FA Cup Preliminary Round |
| 4 | 27/8/2018 | 60-2 v Cray WanderersSittingbourne 0-2 Cray Wanderers | Bostik League South East Division |
| 5 | 4/9/2018 | 22-0 v Phoenix SportsSittingbourne 2-0 Phoenix Sports | Velocity Trophy Preliminary Round |
| 6 | 8/9/2018 | 20-1 v Gosport BoroughSittingbourne 0-1 Gosport Borough | Emirates FA Cup First Qualifying Round |
| 7 | 15/9/2018 | 22-1 v WhyteleafeSittingbourne 2-1 Whyteleafe | Bostik League South East Division |
| 8 | 23/9/2018 | 22-1 v GuernseyGuernsey 1-2 Sittingbourne | Bostik League South East Division |
| 9 | 25/9/2018 | 21-1 v Ashford UnitedAshford United 1-1 Sittingbourne | Bostik League South East Division |
| 10 | 29/9/2018 | 20-1 v RamsgateSittingbourne 0-1 Ramsgate | Bostik League South East Division |
| 11 | 6/10/2018 | 20-2 v Haywards Heath TownHaywards Heath Town 2-0 Sittingbourne | Bostik League South East Division |
| 12 | 13/10/2018 | 22-0 v Faversham TownFaversham Town 0-2 Sittingbourne | Buildbase FA Trophy Preliminary Round |
| 13 | 27/10/2018 | 2 1-2 v Wingate & FinchleySittingbourne 1-2 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 14 | 30/10/2018 | 21-3 v Folkestone InvictaFolkestone Invicta 3-1 Sittingbourne | Velocity Trophy Second Round |
| 15 | 3/11/2018 | 22-3 v Hythe TownHythe Town 3-2 Sittingbourne | Bostik League South East Division |
| 16 | 10/11/2018 | 21-2 v Whitstable TownSittingbourne 1-2 Whitstable Town | Bostik League South East Division |
| 17 | 17/11/2018 | 20-1 v Three BridgesSittingbourne 0-1 Three Bridges | Bostik League South East Division |
| 18 | 24/11/2018 | 21-2 v East Grinstead TownEast Grinstead Town 2-1 Sittingbourne | Bostik League South East Division |
| 19 | 8/12/2018 | 21-3 v Faversham TownFaversham Town 3-1 Sittingbourne | Bostik League South East Division |
| 20 | 15/12/2018 | 34-1 v Sevenoaks TownSittingbourne 4-1 Sevenoaks Town | Bostik League South East Division |
| 21 | 23/12/2018 | 31-2 v Cray WanderersCray Wanderers 2-1 Sittingbourne | Bostik League South East Division |
| 22 | 29/12/2018 | 32-3 v Herne BaySittingbourne 2-3 Herne Bay | Bostik League South East Division |
| 23 | 5/1/2019 | 6 0-5 v Hastings UnitedHastings United 5-0 Sittingbourne | Bostik League South East Division |
| 24 | 19/1/2019 | 30-4 v RamsgateRamsgate 4-0 Sittingbourne | Bostik League South East Division |
| 25 | 22/1/2019 | 41-2 v VCD AthleticSittingbourne 1-2 VCD Athletic | Bostik League South East Division |
| 26 | 26/1/2019 | 21-2 v Haywards Heath TownSittingbourne 1-2 Haywards Heath Town | Bostik League South East Division |
| 27 | 2/2/2019 | 24-3 v Phoenix SportsPhoenix Sports 3-4 Sittingbourne | Bostik League South East Division |
| 28 | 5/2/2019 | 20-2 v Ashford UnitedSittingbourne 0-2 Ashford United | Bostik League South East Division |
| 29 | 16/2/2019 | 22-1 v East Grinstead TownSittingbourne 2-1 East Grinstead Town | Bostik League South East Division |
| 30 | 23/2/2019 | 22-1 v VCD AthleticVCD Athletic 1-2 Sittingbourne | Bostik League South East Division |
| 31 | 26/2/2019 | 25-0 v Three BridgesThree Bridges 0-5 Sittingbourne | Bostik League South East Division |
| 32 | 2/3/2019 | 23-1 v Faversham TownSittingbourne 3-1 Faversham Town | Bostik League South East Division |
| 33 | 9/3/2019 | 21-0 v Sevenoaks TownSevenoaks Town 0-1 Sittingbourne | Bostik League South East Division |
| 34 | 16/3/2019 | 21-2 v Whitstable TownWhitstable Town 2-1 Sittingbourne | Bostik League South East Division |
| 35 | 23/3/2019 | 20-3 v Hythe TownSittingbourne 0-3 Hythe Town | Bostik League South East Division |
| 36 | 30/3/2019 | 21-2 v Greenwich BoroughGreenwich Borough 2-1 Sittingbourne | Bostik League South East Division |
| 37 | 6/4/2019 | 21-6 v HorshamSittingbourne 1-6 Horsham | Bostik League South East Division |
| 38 | 13/4/2019 | 20-3 v WhyteleafeWhyteleafe 3-0 Sittingbourne | Bostik League South East Division |
| 39 | 20/4/2019 | 60-3 v Hastings UnitedSittingbourne 0-3 Hastings United | Bostik League South East Division |
| 40 | 22/4/2019 | 21-1 v Herne BayHerne Bay 1-1 Sittingbourne | Bostik League South East Division |
| 41 | 27/4/2019 | 22-2 v GuernseySittingbourne 2-2 Guernsey | Bostik League South East Division |
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