| 1 | 17/8/2019 | 15 1-1 v Whitstable TownWhitstable Town 1-1 Sittingbourne | BetVictor Isthmian South East Division |
| 2 | 24/8/2019 | 82-0 v UxbridgeSittingbourne 2-0 Uxbridge | Emirates FA Cup Preliminary Round |
| 3 | 26/8/2019 | 142-1 v RamsgateRamsgate 1-2 Sittingbourne | BetVictor Isthmian South East Division |
| 4 | 31/8/2019 | 142-2 v East Grinstead TownSittingbourne 2-2 East Grinstead Town | BetVictor Isthmian South East Division |
| 5 | 3/9/2019 | 42-2 v Sevenoaks TownSevenoaks Town 2-2 Sittingbourne | Velocity Trophy Group 9 |
| 6 | 7/9/2019 | 140-3 v Bognor Regis TownBognor Regis Town 3-0 Sittingbourne | Emirates FA Cup First Qualifying Round |
| 7 | 14/9/2019 | 140-1 v Faversham TownFaversham Town 1-0 Sittingbourne | BetVictor Isthmian South East Division |
