| 1 | 17/8/2019 | 5 2-3 v WhitehawkWhitehawk 3-2 VCD Athletic | BetVictor Isthmian South East Division |
| 2 | 20/8/2019 | 54-3 v Three BridgesVCD Athletic 4-3 Three Bridges | BetVictor Isthmian South East Division |
| 3 | 24/8/2019 | 5 3-3 v Uckfield TownVCD Athletic 3-3 Uckfield Town | Emirates FA Cup Preliminary Round |
| 4 | 31/8/2019 | 122-2 v RamsgateVCD Athletic 2-2 Ramsgate | BetVictor Isthmian South East Division |
| 5 | 3/9/2019 | 21-1 v Uckfield TownUckfield Town 1-1 VCD Athletic | Emirates FA Cup Preliminary Round |
| 6 | 7/9/2019 | 2 1-2 v MoneyfieldsVCD Athletic 1-2 Moneyfields | Emirates FA Cup First Qualifying Round |
| 7 | 14/9/2019 | 122-1 v East Grinstead TownEast Grinstead Town 1-2 VCD Athletic | BetVictor Isthmian South East Division |
| 8 | 17/9/2019 | 122-1 v Faversham TownFaversham Town 1-2 VCD Athletic | BetVictor Isthmian South East Division |
| 9 | 21/9/2019 | 20-0 v Hastings UnitedVCD Athletic 0-0 Hastings United | BetVictor Isthmian South East Division |
| 10 | 24/9/2019 | 54-4 v SittingbourneSittingbourne 4-4 VCD Athletic | Velocity Trophy Group 9 |
| 11 | 28/9/2019 | 22-2 v Cray Valley PMVCD Athletic 2-2 Cray Valley PM | Velocity Trophy Group 9 |
| 12 | 6/10/2019 | 21-3 v GuernseyGuernsey 3-1 VCD Athletic | BetVictor Isthmian South East Division |
| 13 | 12/10/2019 | 141-4 v AFC SudburyVCD Athletic 1-4 AFC Sudbury | Buildbase FA Trophy Preliminary Round |
| 14 | 15/10/2019 | 51-1 v Phoenix SportsVCD Athletic 1-1 Phoenix Sports | Velocity Trophy Group 9 |
| 15 | 26/10/2019 | 51-1 v Whitstable TownWhitstable Town 1-1 VCD Athletic | BetVictor Isthmian South East Division |
| 16 | 30/10/2019 | 52-0 v Cray WanderersCray Wanderers 0-2 VCD Athletic | Kent Senior Cup First Round |
| 17 | 2/11/2019 | 5 2-2 v Sevenoaks TownVCD Athletic 2-2 Sevenoaks Town | BetVictor Isthmian South East Division |
| 18 | 9/11/2019 | 64-1 v Ashford UnitedAshford United 1-4 VCD Athletic | BetVictor Isthmian South East Division |
| 19 | 12/11/2019 | 122-2 v Sevenoaks TownSevenoaks Town 2-2 VCD Athletic | Velocity Trophy Group 9 |
| 20 | 16/11/2019 | 54-0 v Burgess Hill TownVCD Athletic 4-0 Burgess Hill Town | BetVictor Isthmian South East Division |
| 21 | 23/11/2019 | 51-2 v SittingbourneSittingbourne 2-1 VCD Athletic | BetVictor Isthmian South East Division |
| 22 | 30/11/2019 | 52-2 v Haywards Heath TownVCD Athletic 2-2 Haywards Heath Town | BetVictor Isthmian South East Division |
| 23 | 7/12/2019 | 5 2-4 v Herne BayVCD Athletic 2-4 Herne Bay | BetVictor Isthmian South East Division |
