| Kent | ||||
| Date | Home | H | A | Away |
| 08/05/2000 | Beckenham Town | 3 | 1 | Faversham Town |
| 08/05/2000 | Cray Wanderers (+3) | 0 | 1 | Deal Town |
| 05/05/2000 | Beckenham Town | 2 | 3 | Ramsgate |
| 05/05/2000 | Sheppey United (+3) | 0 | 2 | VCD Athletic |
| 03/05/2000 | Chatham Town | 4 | 1 | Deal Town |
| 03/05/2000 | Sheppey United (+3) | 2 | 1 | Whitstable Town |
| 03/05/2000 | VCD Athletic | 2 | 0 | Hythe United |
| 01/05/2000 | Beckenham Town | 2 | 0 | VCD Athletic |
| 01/05/2000 | Canterbury City | 1 | 4 | Chatham Town |
| 01/05/2000 | Ramsgate | 1 | 1 | Erith Town |
| 29/04/2000 | Beckenham Town | 3 | 1 | Whitstable Town |
| 29/04/2000 | Chatham Town | 5 | 0 | Canterbury City |
| 29/04/2000 | Herne Bay (-3) | 6 | 1 | Slade Green |
| 29/04/2000 | Ramsgate | 2 | 0 | Greenwich Borough |
| 29/04/2000 | Tunbridge Wells | 7 | 2 | Erith Town |
| 27/04/2000 | Deal Town | 2 | 0 | Beckenham Town |
| 25/04/2000 | Tunbridge Wells | 1 | 0 | Faversham Town |
| 24/04/2000 | Chatham Town | 6 | 1 | Lordswood |
| 24/04/2000 | Greenwich Borough | 1 | 2 | Slade Green |
| 24/04/2000 | Ramsgate | 2 | 1 | Deal Town |
| 24/04/2000 | VCD Athletic | 2 | 1 | Thamesmead Town (-3) |
| 24/04/2000 | Whitstable Town | 0 | 1 | Hythe United |
| 22/04/2000 | Canterbury City | 0 | 4 | Ramsgate |
| 22/04/2000 | Cray Wanderers (+3) | 3 | 2 | Faversham Town |
| 22/04/2000 | Erith Town | 2 | 0 | Greenwich Borough |
| 22/04/2000 | Hythe United | 2 | 1 | Whitstable Town |
| 22/04/2000 | VCD Athletic | 2 | 1 | Beckenham Town |
| 18/04/2000 | Deal Town | 3 | 3 | Slade Green |
| 18/04/2000 | Hythe United | 1 | 1 | Faversham Town |
| 18/04/2000 | Sheppey United (+3) | 2 | 3 | Chatham Town |
| 15/04/2000 | Deal Town | 2 | 0 | Thamesmead Town (-3) |
| 15/04/2000 | Greenwich Borough | 0 | 1 | Erith Town |
| 13/04/2000 | Deal Town | 3 | 0 | Lordswood |
| 11/04/2000 | Faversham Town | 0 | 1 | Thamesmead Town (-3) |
| 11/04/2000 | Hythe United | 1 | 3 | Deal Town |
| 11/04/2000 | Ramsgate | 4 | 4 | Herne Bay (-3) |
| 10/04/2000 | Erith Town | 2 | 0 | Beckenham Town |
| 08/04/2000 | Canterbury City | 0 | 4 | Beckenham Town |
| 08/04/2000 | Cray Wanderers (+3) | 1 | 1 | Whitstable Town |
| 08/04/2000 | Greenwich Borough | 1 | 3 | Chatham Town |
| 08/04/2000 | Lordswood | 5 | 3 | Erith Town |
| 08/04/2000 | Thamesmead Town (-3) | 5 | 0 | Slade Green |
| 01/04/2000 | Beckenham Town | 1 | 0 | Cray Wanderers (+3) |
| 01/04/2000 | Erith Town | 1 | 4 | Chatham Town |
| 01/04/2000 | Hythe United | 4 | 1 | Herne Bay (-3) |
| 01/04/2000 | Lordswood | 2 | 2 | Tunbridge Wells |
| 01/04/2000 | Sheppey United (+3) | 2 | 1 | Slade Green |
| 01/04/2000 | Whitstable Town | 0 | 2 | Canterbury City |
| 28/03/2000 | Canterbury City | 2 | 3 | VCD Athletic |
| 28/03/2000 | Faversham Town | 1 | 1 | Erith Town |
| 28/03/2000 | Sheppey United (+3) | 0 | 4 | Deal Town |
| 28/03/2000 | Whitstable Town | 1 | 0 | Ramsgate |
| 25/03/2000 | Cray Wanderers (+3) | 2 | 0 | Canterbury City |
| 25/03/2000 | Erith Town | 1 | 1 | VCD Athletic |
| 25/03/2000 | Faversham Town | 0 | 2 | Beckenham Town |
| 25/03/2000 | Herne Bay (-3) | 1 | 2 | Greenwich Borough |
| 25/03/2000 | Hythe United | 2 | 0 | Lordswood |
| 25/03/2000 | Ramsgate | 2 | 2 | Tunbridge Wells |
| 25/03/2000 | Thamesmead Town (-3) | 1 | 2 | Sheppey United (+3) |
| 22/03/2000 | VCD Athletic | 0 | 3 | Lordswood |
| 21/03/2000 | Canterbury City | 1 | 2 | Deal Town |
| 21/03/2000 | Chatham Town | 0 | 0 | Whitstable Town |
| 21/03/2000 | Slade Green | 5 | 0 | Faversham Town |
| 18/03/2000 | Beckenham Town | 0 | 1 | Lordswood |
| 18/03/2000 | Cray Wanderers (+3) | 1 | 4 | Herne Bay (-3) |
| 18/03/2000 | Erith Town | 2 | 1 | Canterbury City |
| 18/03/2000 | Greenwich Borough | 0 | 1 | Tunbridge Wells |
| 18/03/2000 | Sheppey United (+3) | 1 | 3 | Hythe United |
| 18/03/2000 | Slade Green | 1 | 4 | Ramsgate |
| 18/03/2000 | Whitstable Town | 3 | 4 | VCD Athletic |
| 15/03/2000 | VCD Athletic | 3 | 0 | Tunbridge Wells |
| 14/03/2000 | Canterbury City | 3 | 1 | Faversham Town |
| 14/03/2000 | Deal Town | 2 | 1 | Whitstable Town |
| 11/03/2000 | Greenwich Borough | 0 | 2 | VCD Athletic |
| 11/03/2000 | Herne Bay (-3) | 0 | 0 | Sheppey United (+3) |
| 11/03/2000 | Hythe United | 2 | 1 | Beckenham Town |
| 11/03/2000 | Lordswood | 4 | 0 | Faversham Town |
| 11/03/2000 | Ramsgate | 3 | 0 | Cray Wanderers (+3) |
| 11/03/2000 | Tunbridge Wells | 1 | 2 | Canterbury City |
| 11/03/2000 | Whitstable Town | 4 | 4 | Erith Town |
| 07/03/2000 | Faversham Town | 0 | 2 | Chatham Town |
| 07/03/2000 | Thamesmead Town (-3) | 1 | 1 | Deal Town |
| 06/03/2000 | Erith Town | 0 | 2 | Ramsgate |
| 04/03/2000 | Chatham Town | 2 | 1 | Sheppey United (+3) |
| 04/03/2000 | Erith Town | 3 | 1 | Cray Wanderers (+3) |
| 04/03/2000 | Tunbridge Wells | 1 | 3 | Thamesmead Town (-3) |
| 04/03/2000 | VCD Athletic | 1 | 0 | Slade Green |
| 01/03/2000 | Thamesmead Town (-3) | 1 | 0 | Whitstable Town |
| 26/02/2000 | Canterbury City | 1 | 1 | Herne Bay (-3) |
| 26/02/2000 | Cray Wanderers (+3) | 4 | 3 | Chatham Town |
| 26/02/2000 | Erith Town | 2 | 2 | Deal Town |
| 26/02/2000 | Faversham Town | 1 | 2 | Greenwich Borough |
| 26/02/2000 | Hythe United | 0 | 2 | Thamesmead Town (-3) |
| 26/02/2000 | Ramsgate | 4 | 1 | Slade Green |
| 26/02/2000 | Sheppey United (+3) | 1 | 5 | Lordswood |
| 26/02/2000 | Whitstable Town | 1 | 1 | Tunbridge Wells |
| 23/02/2000 | VCD Athletic | 2 | 1 | Cray Wanderers (+3) |
| 22/02/2000 | Deal Town | 3 | 1 | Faversham Town |
| 22/02/2000 | Greenwich Borough | 2 | 0 | Canterbury City |
| 22/02/2000 | Ramsgate | 2 | 0 | Chatham Town |
| 21/02/2000 | Erith Town | 2 | 3 | Slade Green |
| 19/02/2000 | Canterbury City | 3 | 5 | Thamesmead Town (-3) |
| 19/02/2000 | Chatham Town | 4 | 0 | Faversham Town |
| 19/02/2000 | Cray Wanderers (+3) | 3 | 2 | Hythe United |
| 19/02/2000 | Deal Town | 3 | 1 | Greenwich Borough |
| 19/02/2000 | Herne Bay (-3) | 0 | 1 | VCD Athletic |
| 19/02/2000 | Ramsgate | 1 | 0 | Lordswood |
| 19/02/2000 | Tunbridge Wells | 4 | 0 | Sheppey United (+3) |
| 16/02/2000 | VCD Athletic | 2 | 1 | Sheppey United (+3) |
| 15/02/2000 | Canterbury City | 2 | 2 | Whitstable Town |
| 15/02/2000 | Chatham Town | 2 | 0 | Beckenham Town |
| 15/02/2000 | Faversham Town | 3 | 1 | Ramsgate |
| 12/02/2000 | Greenwich Borough | 1 | 2 | Cray Wanderers (+3) |
| 12/02/2000 | Lordswood | 0 | 1 | Thamesmead Town (-3) |
| 12/02/2000 | Slade Green | 2 | 2 | Whitstable Town |
| 09/02/2000 | Cray Wanderers (+3) | 2 | 0 | Slade Green |
| 05/02/2000 | Cray Wanderers (+3) | 2 | 1 | Tunbridge Wells |
| 05/02/2000 | Herne Bay (-3) | 1 | 2 | Hythe United |
| 05/02/2000 | Thamesmead Town (-3) | 1 | 0 | Greenwich Borough |
| 01/02/2000 | Canterbury City | 1 | 1 | Sheppey United (+3) |
| 29/01/2000 | Deal Town | 1 | 0 | VCD Athletic |
| 29/01/2000 | Erith Town | 1 | 1 | Sheppey United (+3) |
| 29/01/2000 | Faversham Town | 1 | 0 | Whitstable Town |
| 29/01/2000 | Herne Bay (-3) | 3 | 1 | Tunbridge Wells |
| 29/01/2000 | Hythe United | 1 | 0 | Chatham Town |
| 29/01/2000 | Lordswood | 5 | 1 | Canterbury City |
| 29/01/2000 | Slade Green | 0 | 0 | Beckenham Town |
| 29/01/2000 | Thamesmead Town (-3) | 1 | 0 | Cray Wanderers (+3) |
| 25/01/2000 | Beckenham Town | 0 | 3 | Erith Town |
| 25/01/2000 | Canterbury City | 0 | 0 | Slade Green |
| 25/01/2000 | Sheppey United (+3) | 1 | 0 | Ramsgate |
| 25/01/2000 | Thamesmead Town (-3) | 3 | 0 | Lordswood |
| 25/01/2000 | Whitstable Town | 0 | 2 | Greenwich Borough |
| 22/01/2000 | Chatham Town | 1 | 5 | Herne Bay (-3) |
| 22/01/2000 | Cray Wanderers (+3) | 2 | 1 | Sheppey United (+3) |
| 22/01/2000 | Faversham Town | 4 | 2 | Slade Green |
| 22/01/2000 | Hythe United | 1 | 0 | Canterbury City |
| 22/01/2000 | Tunbridge Wells | 1 | 1 | Beckenham Town |
| 15/01/2000 | Beckenham Town | 1 | 1 | Herne Bay (-3) |
| 15/01/2000 | Canterbury City | 0 | 3 | Cray Wanderers (+3) |
| 15/01/2000 | Greenwich Borough | 2 | 2 | Thamesmead Town (-3) |
| 15/01/2000 | Lordswood | 3 | 0 | Hythe United |
| 15/01/2000 | Sheppey United (+3) | 2 | 1 | Faversham Town |
| 15/01/2000 | Slade Green | 0 | 2 | Deal Town |
| 15/01/2000 | Tunbridge Wells | 3 | 1 | Ramsgate |
| 15/01/2000 | VCD Athletic | 1 | 1 | Erith Town |
| 15/01/2000 | Whitstable Town | 1 | 3 | Chatham Town |
| 12/01/2000 | Cray Wanderers (+3) | 2 | 2 | Beckenham Town |
| 11/01/2000 | Chatham Town | 3 | 2 | VCD Athletic |
| 11/01/2000 | Deal Town | 1 | 0 | Sheppey United (+3) |
| 11/01/2000 | Faversham Town | 1 | 4 | Herne Bay (-3) |
| 11/01/2000 | Thamesmead Town (-3) | 4 | 1 | Erith Town |
| 08/01/2000 | Erith Town | 1 | 0 | Tunbridge Wells |
| 08/01/2000 | Faversham Town | 0 | 1 | Hythe United |
| 08/01/2000 | Greenwich Borough | 4 | 1 | Sheppey United (+3) |
| 08/01/2000 | Herne Bay (-3) | 0 | 1 | Ramsgate |
| 03/01/2000 | Beckenham Town | 2 | 1 | Thamesmead Town (-3) |
| 03/01/2000 | Herne Bay (-3) | 3 | 1 | Whitstable Town |
| 03/01/2000 | Lordswood | 1 | 4 | Deal Town |
| 03/01/2000 | VCD Athletic | 1 | 1 | Chatham Town |
| 28/12/1999 | Chatham Town | 3 | 0 | Greenwich Borough |
| 28/12/1999 | Deal Town | 3 | 0 | Herne Bay (-3) |
| 28/12/1999 | Faversham Town | 1 | 2 | Sheppey United (+3) |
| 28/12/1999 | Hythe United | 2 | 0 | Tunbridge Wells |
| 28/12/1999 | Slade Green | 0 | 1 | Lordswood |
| 28/12/1999 | Thamesmead Town (-3) | 2 | 0 | Beckenham Town |
| 27/12/1999 | Cray Wanderers (+3) | 1 | 3 | Erith Town |
| 18/12/1999 | Erith Town | 2 | 0 | Herne Bay (-3) |
| 18/12/1999 | Lordswood | 1 | 2 | Greenwich Borough |
| 18/12/1999 | Ramsgate | 1 | 1 | VCD Athletic |
| 18/12/1999 | Sheppey United (+3) | 2 | 4 | Beckenham Town |
| 18/12/1999 | Slade Green | 0 | 2 | Hythe United |
| 18/12/1999 | Thamesmead Town (-3) | 4 | 1 | Chatham Town |
| 18/12/1999 | Tunbridge Wells | 1 | 4 | Deal Town |
| 14/12/1999 | Chatham Town | 1 | 0 | Erith Town |
| 11/12/1999 | Beckenham Town | 3 | 1 | Tunbridge Wells |
| 11/12/1999 | Herne Bay (-3) | 1 | 1 | Thamesmead Town (-3) |
| 11/12/1999 | Slade Green | 0 | 2 | Chatham Town |
| 04/12/1999 | Herne Bay (-3) | 1 | 2 | Faversham Town |
| 04/12/1999 | Hythe United | 1 | 3 | Erith Town |
| 04/12/1999 | Whitstable Town | 4 | 0 | Cray Wanderers (+3) |
| 27/11/1999 | Chatham Town | 2 | 1 | Cray Wanderers (+3) |
| 27/11/1999 | Deal Town | 6 | 0 | Erith Town |
| 27/11/1999 | Greenwich Borough | 4 | 1 | Faversham Town |
| 27/11/1999 | Herne Bay (-3) | 0 | 0 | Beckenham Town |
| 27/11/1999 | Hythe United | 2 | 4 | Sheppey United (+3) |
| 27/11/1999 | Lordswood | 2 | 5 | Ramsgate |
| 27/11/1999 | Slade Green | 0 | 1 | Thamesmead Town (-3) |
| 27/11/1999 | Tunbridge Wells | 3 | 2 | Whitstable Town |
| 27/11/1999 | VCD Athletic | 3 | 0 | Canterbury City |
| 24/11/1999 | Cray Wanderers (+3) | 3 | 4 | Greenwich Borough |
| 24/11/1999 | Faversham Town | 1 | 2 | Canterbury City |
| 23/11/1999 | Beckenham Town | 3 | 1 | Deal Town |
| 23/11/1999 | Chatham Town | 0 | 2 | Ramsgate |
| 20/11/1999 | Cray Wanderers (+3) | 0 | 2 | VCD Athletic |
| 20/11/1999 | Erith Town | 0 | 0 | Hythe United |
| 20/11/1999 | Lordswood | 2 | 2 | Herne Bay (-3) |
| 20/11/1999 | Ramsgate | 6 | 2 | Beckenham Town |
| 20/11/1999 | Sheppey United (+3) | 1 | 3 | Greenwich Borough |
| 20/11/1999 | Thamesmead Town (-3) | 1 | 2 | Tunbridge Wells |
| 20/11/1999 | Whitstable Town | 0 | 1 | Deal Town |
| 16/11/1999 | Faversham Town | 4 | 0 | Cray Wanderers (+3) |
| 16/11/1999 | Herne Bay (-3) | 1 | 3 | Erith Town |
| 16/11/1999 | Thamesmead Town (-3) | 1 | 0 | Hythe United |
| 13/11/1999 | Beckenham Town | 3 | 0 | Canterbury City |
| 13/11/1999 | Slade Green | 1 | 3 | Tunbridge Wells |
| 12/11/1999 | Greenwich Borough | 4 | 2 | Whitstable Town |
| 12/11/1999 | VCD Athletic | 2 | 2 | Faversham Town |
| 10/11/1999 | Lordswood | 4 | 1 | Cray Wanderers (+3) |
| 06/11/1999 | Greenwich Borough | 0 | 0 | Hythe United |
| 30/10/1999 | Beckenham Town | 0 | 4 | Greenwich Borough |
| 30/10/1999 | Canterbury City | 1 | 1 | Hythe United |
| 30/10/1999 | Deal Town | 5 | 0 | Cray Wanderers (+3) |
| 30/10/1999 | Erith Town | 1 | 0 | Lordswood |
| 30/10/1999 | Faversham Town | 5 | 0 | Tunbridge Wells |
| 30/10/1999 | Herne Bay (-3) | 0 | 1 | Chatham Town |
| 30/10/1999 | Slade Green | 2 | 1 | Sheppey United (+3) |
| 30/10/1999 | VCD Athletic | 1 | 2 | Ramsgate |
| 30/10/1999 | Whitstable Town | 1 | 1 | Thamesmead Town (-3) |
| 26/10/1999 | Herne Bay (-3) | 2 | 1 | Canterbury City |
| 26/10/1999 | Hythe United | 0 | 1 | Greenwich Borough |
| 26/10/1999 | Ramsgate | 1 | 3 | Whitstable Town |
| 23/10/1999 | Ramsgate | 1 | 0 | Canterbury City |
| 23/10/1999 | Sheppey United (+3) | 0 | 1 | Herne Bay (-3) |
| 23/10/1999 | Tunbridge Wells | 1 | 3 | Slade Green |
| 23/10/1999 | Whitstable Town | 2 | 0 | Lordswood |
| 16/10/1999 | Deal Town | 3 | 1 | Chatham Town |
| 16/10/1999 | Erith Town | 1 | 0 | Faversham Town |
| 16/10/1999 | Lordswood | 0 | 0 | Beckenham Town |
| 16/10/1999 | Ramsgate | 0 | 0 | Sheppey United (+3) |
| 16/10/1999 | Slade Green | 1 | 2 | Herne Bay (-3) |
| 16/10/1999 | Thamesmead Town (-3) | 6 | 0 | Canterbury City |
| 16/10/1999 | Tunbridge Wells | 1 | 3 | VCD Athletic |
| 09/10/1999 | Chatham Town | 2 | 0 | Tunbridge Wells |
| 09/10/1999 | Greenwich Borough | 0 | 0 | Deal Town |
| 09/10/1999 | Lordswood | 1 | 1 | Slade Green |
| 09/10/1999 | Thamesmead Town (-3) | 1 | 1 | Ramsgate |
| 09/10/1999 | Whitstable Town | 1 | 1 | Sheppey United (+3) |
| 06/10/1999 | Cray Wanderers (+3) | 2 | 2 | Lordswood |
| 02/10/1999 | Beckenham Town | 0 | 1 | Sheppey United (+3) |
| 02/10/1999 | Chatham Town | 1 | 2 | Thamesmead Town (-3) |
| 02/10/1999 | Cray Wanderers (+3) | 1 | 7 | Ramsgate |
| 02/10/1999 | Deal Town | 3 | 1 | Tunbridge Wells |
| 02/10/1999 | Greenwich Borough | 6 | 1 | Lordswood |
| 02/10/1999 | Hythe United | 1 | 2 | Slade Green |
| 02/10/1999 | VCD Athletic | 1 | 0 | Whitstable Town |
| 25/09/1999 | Herne Bay (-3) | 2 | 3 | Deal Town |
| 18/09/1999 | Beckenham Town | 4 | 1 | Hythe United |
| 18/09/1999 | Canterbury City | 3 | 2 | Tunbridge Wells |
| 18/09/1999 | Erith Town | 3 | 0 | Whitstable Town |
| 18/09/1999 | Faversham Town | 1 | 1 | Lordswood |
| 18/09/1999 | Sheppey United (+3) | 2 | 3 | Thamesmead Town (-3) |
| 18/09/1999 | Slade Green | 1 | 2 | Cray Wanderers (+3) |
| 18/09/1999 | VCD Athletic | 3 | 0 | Greenwich Borough |
| 11/09/1999 | Deal Town | 5 | 1 | Canterbury City |
| 11/09/1999 | Erith Town | 1 | 4 | Thamesmead Town (-3) |
| 11/09/1999 | Greenwich Borough | 2 | 0 | Herne Bay (-3) |
| 11/09/1999 | Lordswood | 0 | 2 | Sheppey United (+3) |
| 11/09/1999 | Ramsgate | 0 | 1 | Hythe United |
| 11/09/1999 | Tunbridge Wells | 2 | 1 | Cray Wanderers (+3) |
| 11/09/1999 | Whitstable Town | 0 | 3 | Slade Green |
| 07/09/1999 | Herne Bay (-3) | 3 | 0 | Cray Wanderers (+3) |
| 04/09/1999 | Greenwich Borough | 5 | 0 | Beckenham Town |
| 04/09/1999 | Hythe United | 0 | 0 | VCD Athletic |
| 04/09/1999 | Slade Green | 1 | 2 | Canterbury City |
| 04/09/1999 | Thamesmead Town (-3) | 3 | 0 | Faversham Town |
| 04/09/1999 | Tunbridge Wells | 1 | 3 | Lordswood |
| 30/08/1999 | Deal Town | 0 | 0 | Ramsgate |
| 30/08/1999 | Lordswood | 1 | 3 | Chatham Town |
| 30/08/1999 | Slade Green | 2 | 4 | Greenwich Borough |
| 30/08/1999 | Thamesmead Town (-3) | 1 | 1 | VCD Athletic |
| 30/08/1999 | Tunbridge Wells | 0 | 0 | Hythe United |
| 30/08/1999 | Whitstable Town | 1 | 0 | Herne Bay (-3) |
| 28/08/1999 | Beckenham Town | 0 | 3 | Slade Green |
| 28/08/1999 | Canterbury City | 1 | 3 | Lordswood |
| 28/08/1999 | Chatham Town | 2 | 0 | Hythe United |
| 28/08/1999 | Cray Wanderers (+3) | 0 | 5 | Thamesmead Town (-3) |
| 28/08/1999 | Greenwich Borough | 1 | 1 | Ramsgate |
| 28/08/1999 | Sheppey United (+3) | 2 | 1 | Erith Town |
| 28/08/1999 | Tunbridge Wells | 1 | 4 | Herne Bay (-3) |
| 28/08/1999 | VCD Athletic | 0 | 2 | Deal Town |
| 28/08/1999 | Whitstable Town | 1 | 0 | Faversham Town |
| 24/08/1999 | Sheppey United (+3) | 4 | 4 | Canterbury City |
| 24/08/1999 | Slade Green | 0 | 0 | VCD Athletic |
| 21/08/1999 | Faversham Town | 1 | 1 | VCD Athletic |
| 14/08/1999 | Beckenham Town | 1 | 1 | Chatham Town |
| 14/08/1999 | Canterbury City | 0 | 10 | Greenwich Borough |
| 14/08/1999 | Faversham Town | 0 | 4 | Deal Town |
| 14/08/1999 | Hythe United | 3 | 1 | Cray Wanderers (+3) |
| 14/08/1999 | Lordswood | 2 | 1 | Whitstable Town |
| 14/08/1999 | Ramsgate | 2 | 5 | Thamesmead Town (-3) |
| 14/08/1999 | Sheppey United (+3) | 3 | 0 | Tunbridge Wells |
| 14/08/1999 | Slade Green | 0 | 2 | Erith Town |
| 14/08/1999 | VCD Athletic | 1 | 1 | Herne Bay (-3) |
| 10/08/1999 | Herne Bay (-3) | 2 | 1 | Lordswood |
| 10/08/1999 | Hythe United | 0 | 6 | Ramsgate |
| 10/08/1999 | Tunbridge Wells | 2 | 4 | Chatham Town |
| 07/08/1999 | Canterbury City | 0 | 2 | Erith Town |
| 07/08/1999 | Chatham Town | 2 | 0 | Slade Green |
| 07/08/1999 | Deal Town | 6 | 1 | Hythe United |
| 07/08/1999 | Lordswood | 0 | 3 | VCD Athletic |
| 07/08/1999 | Ramsgate | 3 | 3 | Faversham Town |
| 07/08/1999 | Sheppey United (+3) | 1 | 0 | Cray Wanderers (+3) |
| 07/08/1999 | Thamesmead Town (-3) | 1 | 0 | Herne Bay (-3) |
| 07/08/1999 | Tunbridge Wells | 2 | 2 | Greenwich Borough |
| 07/08/1999 | Whitstable Town | 0 | 0 | Beckenham Town |