| 1 | 11/8/2018 | 172-1 v HorshamHorsham 1-2 Sittingbourne | Bostik League South East Division |
| 2 | 18/8/2018 | 164-2 v Greenwich BoroughSittingbourne 4-2 Greenwich Borough | Bostik League South East Division |
| 3 | 25/8/2018 | 172-0 v BearstedSittingbourne 2-0 Bearsted | Emirates FA Cup Preliminary Round |
| 4 | 27/8/2018 | 160-2 v Cray WanderersSittingbourne 0-2 Cray Wanderers | Bostik League South East Division |
| 5 | 4/9/2018 | 122-0 v Phoenix SportsSittingbourne 2-0 Phoenix Sports | Velocity Trophy Preliminary Round |
| 6 | 15/9/2018 | 152-1 v WhyteleafeSittingbourne 2-1 Whyteleafe | Bostik League South East Division |
| 7 | 23/9/2018 | 152-1 v GuernseyGuernsey 1-2 Sittingbourne | Bostik League South East Division |
| 8 | 25/9/2018 | 161-1 v Ashford UnitedAshford United 1-1 Sittingbourne | Bostik League South East Division |
| 9 | 2/10/2018 | 92-1 v South ParkSouth Park 1-2 Sittingbourne | Velocity Trophy First Round |
| 10 | 6/10/2018 | 90-2 v Haywards Heath TownHaywards Heath Town 2-0 Sittingbourne | Bostik League South East Division |
| 11 | 13/10/2018 | 152-0 v Faversham TownFaversham Town 0-2 Sittingbourne | Buildbase FA Trophy Preliminary Round |
| 12 | 20/10/2018 | 161-1 v Phoenix SportsSittingbourne 1-1 Phoenix Sports | Bostik League South East Division |
| 13 | 27/10/2018 | 161-2 v Wingate & FinchleySittingbourne 1-2 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 14 | 30/10/2018 | 161-3 v Folkestone InvictaFolkestone Invicta 3-1 Sittingbourne | Velocity Trophy Second Round |
| 15 | 10/11/2018 | 151-2 v Whitstable TownSittingbourne 1-2 Whitstable Town | Bostik League South East Division |
| 16 | 22/1/2019 | 161-2 v VCD AthleticSittingbourne 1-2 VCD Athletic | Bostik League South East Division |
| 17 | 26/1/2019 | 171-2 v Haywards Heath TownSittingbourne 1-2 Haywards Heath Town | Bostik League South East Division |
| 18 | 2/2/2019 | 164-3 v Phoenix SportsPhoenix Sports 3-4 Sittingbourne | Bostik League South East Division |
| 19 | 5/2/2019 | 100-2 v Ashford UnitedSittingbourne 0-2 Ashford United | Bostik League South East Division |
| 20 | 16/2/2019 | 9 2-1 v East Grinstead TownSittingbourne 2-1 East Grinstead Town | Bostik League South East Division |
| 21 | 16/3/2019 | 171-2 v Whitstable TownWhitstable Town 2-1 Sittingbourne | Bostik League South East Division |
| 22 | 23/3/2019 | 170-3 v Hythe TownSittingbourne 0-3 Hythe Town | Bostik League South East Division |
| 23 | 13/4/2019 | 90-3 v WhyteleafeWhyteleafe 3-0 Sittingbourne | Bostik League South East Division |
