| 1 | Sat 17 Aug 2019 | 61-1 v Whitstable TownWhitstable Town 1-1 Sittingbourne |
| 2 | Tue 20 Aug 2019 | 6 1-3 v Cray Valley PMSittingbourne 1-3 Cray Valley PM |
| 3 | Sat 31 Aug 2019 | 62-2 v East Grinstead TownSittingbourne 2-2 East Grinstead Town |
| 4 | Sat 14 Sep 2019 | 50-1 v Faversham TownFaversham Town 1-0 Sittingbourne |
| 5 | Tue 17 Sep 2019 | 61-2 v Ashford UnitedAshford United 2-1 Sittingbourne |
| 6 | Sat 21 Sep 2019 | 50-1 v GuernseySittingbourne 0-1 Guernsey |
| 7 | Sat 19 Oct 2019 | 51-0 v Hythe TownSittingbourne 1-0 Hythe Town |
| 8 | Sat 9 Nov 2019 | 52-0 v Herne BaySittingbourne 2-0 Herne Bay |
| 9 | Sat 16 Nov 2019 | 61-1 v Chichester CityChichester City 1-1 Sittingbourne |
| 10 | Sat 23 Nov 2019 | 62-1 v VCD AthleticSittingbourne 2-1 VCD Athletic |
| 11 | Sat 30 Nov 2019 | 51-2 v Burgess Hill TownBurgess Hill Town 2-1 Sittingbourne |
| 12 | Tue 3 Dec 2019 | 61-2 v WhyteleafeWhyteleafe 2-1 Sittingbourne |
| 13 | Sat 7 Dec 2019 | 52-1 v Sevenoaks TownSevenoaks Town 1-2 Sittingbourne |
| 14 | Tue 10 Dec 2019 | 50-1 v Hastings UnitedSittingbourne 0-1 Hastings United |
| 15 | Sat 28 Dec 2019 | 57-0 v RamsgateSittingbourne 7-0 Ramsgate |
| 16 | Sat 4 Jan 2020 | 52-1 v East Grinstead TownEast Grinstead Town 1-2 Sittingbourne |
| 17 | Sat 11 Jan 2020 | 51-0 v Three BridgesSittingbourne 1-0 Three Bridges |
| 18 | Sat 18 Jan 2020 | 50-1 v Hythe TownHythe Town 1-0 Sittingbourne |
| 19 | Tue 21 Jan 2020 | 51-1 v WhitehawkSittingbourne 1-1 Whitehawk |
| 20 | Sat 25 Jan 2020 | 5 0-1 v WhyteleafeSittingbourne 0-1 Whyteleafe |
| 21 | Sat 1 Feb 2020 | 51-3 v GuernseyGuernsey 3-1 Sittingbourne |
| 22 | Tue 4 Feb 2020 | 50-1 v Ashford UnitedSittingbourne 0-1 Ashford United |
| 23 | Sat 8 Feb 2020 | 50-1 v WhitehawkWhitehawk 1-0 Sittingbourne |
| 24 | Sat 22 Feb 2020 | 50-4 v Hastings UnitedHastings United 4-0 Sittingbourne |
| 25 | Tue 25 Feb 2020 | 50-3 v Phoenix SportsPhoenix Sports 3-0 Sittingbourne |
| 26 | Tue 3 Mar 2020 | 51-2 v Haywards Heath TownHaywards Heath Town 2-1 Sittingbourne |
| 27 | Tue 10 Mar 2020 | 50-3 v Sevenoaks TownSittingbourne 0-3 Sevenoaks Town |
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