| 1 | 11/8/2018 | 42-1 v HorshamHorsham 1-2 Sittingbourne | Bostik League South East Division |
| 2 | 18/8/2018 | 44-2 v Greenwich BoroughSittingbourne 4-2 Greenwich Borough | Bostik League South East Division |
| 3 | 25/8/2018 | 42-0 v BearstedSittingbourne 2-0 Bearsted | Emirates FA Cup Preliminary Round |
| 4 | 27/8/2018 | 4 0-2 v Cray WanderersSittingbourne 0-2 Cray Wanderers | Bostik League South East Division |
| 5 | 8/9/2018 | 40-1 v Gosport BoroughSittingbourne 0-1 Gosport Borough | Emirates FA Cup First Qualifying Round |
| 6 | 15/9/2018 | 42-1 v WhyteleafeSittingbourne 2-1 Whyteleafe | Bostik League South East Division |
| 7 | 23/9/2018 | 8 2-1 v GuernseyGuernsey 1-2 Sittingbourne | Bostik League South East Division |
| 8 | 25/9/2018 | 41-1 v Ashford UnitedAshford United 1-1 Sittingbourne | Bostik League South East Division |
| 9 | 29/9/2018 | 40-1 v RamsgateSittingbourne 0-1 Ramsgate | Bostik League South East Division |
| 10 | 6/10/2018 | 40-2 v Haywards Heath TownHaywards Heath Town 2-0 Sittingbourne | Bostik League South East Division |
| 11 | 13/10/2018 | 142-0 v Faversham TownFaversham Town 0-2 Sittingbourne | Buildbase FA Trophy Preliminary Round |
| 12 | 20/10/2018 | 141-1 v Phoenix SportsSittingbourne 1-1 Phoenix Sports | Bostik League South East Division |
| 13 | 27/10/2018 | 41-2 v Wingate & FinchleySittingbourne 1-2 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 14 | 30/10/2018 | 41-3 v Folkestone InvictaFolkestone Invicta 3-1 Sittingbourne | Velocity Trophy Second Round |
| 15 | 3/11/2018 | 42-3 v Hythe TownHythe Town 3-2 Sittingbourne | Bostik League South East Division |
| 16 | 10/11/2018 | 4 1-2 v Whitstable TownSittingbourne 1-2 Whitstable Town | Bostik League South East Division |
| 17 | 15/12/2018 | 84-1 v Sevenoaks TownSittingbourne 4-1 Sevenoaks Town | Bostik League South East Division |
| 18 | 23/12/2018 | 4 1-2 v Cray WanderersCray Wanderers 2-1 Sittingbourne | Bostik League South East Division |
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