| 1 | Sat 18 Aug 2018 | 10 4-2 v Greenwich BoroughSittingbourne 4-2 Greenwich Borough |
| 2 | Mon 27 Aug 2018 | 10 0-2 v Cray WanderersSittingbourne 0-2 Cray Wanderers |
| 3 | Sat 15 Sep 2018 | 102-1 v WhyteleafeSittingbourne 2-1 Whyteleafe |
| 4 | Sun 23 Sep 2018 | 102-1 v GuernseyGuernsey 1-2 Sittingbourne |
| 5 | Tue 25 Sep 2018 | 10 1-1 v Ashford UnitedAshford United 1-1 Sittingbourne |
| 6 | Sat 29 Sep 2018 | 10 0-1 v RamsgateSittingbourne 0-1 Ramsgate |
| 7 | Sat 3 Nov 2018 | 72-3 v Hythe TownHythe Town 3-2 Sittingbourne |
| 8 | Sat 10 Nov 2018 | 10 1-2 v Whitstable TownSittingbourne 1-2 Whitstable Town |
| 9 | Sat 17 Nov 2018 | 100-1 v Three BridgesSittingbourne 0-1 Three Bridges |
| 10 | Sat 24 Nov 2018 | 101-2 v East Grinstead TownEast Grinstead Town 2-1 Sittingbourne |
| 11 | Sat 8 Dec 2018 | 101-3 v Faversham TownFaversham Town 3-1 Sittingbourne |
| 12 | Sat 15 Dec 2018 | 10 4-1 v Sevenoaks TownSittingbourne 4-1 Sevenoaks Town |
| 13 | Sun 23 Dec 2018 | 101-2 v Cray WanderersCray Wanderers 2-1 Sittingbourne |
| 14 | Sat 29 Dec 2018 | 10 2-3 v Herne BaySittingbourne 2-3 Herne Bay |
| 15 | Sat 5 Jan 2019 | 100-5 v Hastings UnitedHastings United 5-0 Sittingbourne |
| 16 | Sat 19 Jan 2019 | 80-4 v RamsgateRamsgate 4-0 Sittingbourne |
| 17 | Tue 22 Jan 2019 | 8 1-2 v VCD AthleticSittingbourne 1-2 VCD Athletic |
| 18 | Sat 26 Jan 2019 | 51-2 v Haywards Heath TownSittingbourne 1-2 Haywards Heath Town |
| 19 | Sat 2 Feb 2019 | 54-3 v Phoenix SportsPhoenix Sports 3-4 Sittingbourne |
| 20 | Tue 5 Feb 2019 | 40-2 v Ashford UnitedSittingbourne 0-2 Ashford United |
| 21 | Tue 26 Feb 2019 | 45-0 v Three BridgesThree Bridges 0-5 Sittingbourne |
| 22 | Sat 2 Mar 2019 | 43-1 v Faversham TownSittingbourne 3-1 Faversham Town |
| 23 | Sat 9 Mar 2019 | 41-0 v Sevenoaks TownSevenoaks Town 0-1 Sittingbourne |
| 24 | Sat 6 Apr 2019 | 5 1-6 v HorshamSittingbourne 1-6 Horsham |
| 25 | Sat 13 Apr 2019 | 50-3 v WhyteleafeWhyteleafe 3-0 Sittingbourne |
| 26 | Sat 20 Apr 2019 | 50-3 v Hastings UnitedSittingbourne 0-3 Hastings United |
| 27 | Mon 22 Apr 2019 | 61-1 v Herne BayHerne Bay 1-1 Sittingbourne |
| 28 | Sat 27 Apr 2019 | 6 2-2 v GuernseySittingbourne 2-2 Guernsey |
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