| Kent County | ||||
| Date | Home | H | A | Away |
| 13/05/2000 | Bearsted | 4 | 1 | Stansfield O&BC |
| 13/05/2000 | Sevenoaks Town | 1 | 1 | Lydd Town |
| 06/05/2000 | Bearsted | 1 | 0 | Sevenoaks Town |
| 06/05/2000 | Knatchbull | 1 | 1 | Stansfield O&BC |
| 06/05/2000 | Milton Athletic | 1 | 1 | Maidstone United (P) |
| 06/05/2000 | Sheerness East (P) | 3 | 1 | Lydd Town |
| 06/05/2000 | Thames Polytechnic | 6 | 0 | Aylesford PM |
| 03/05/2000 | Sheerness East (P) | 1 | 2 | Bearsted |
| 01/05/2000 | Snodland | 1 | 0 | Bearsted |
| 29/04/2000 | Bearsted | 4 | 1 | Thames Polytechnic |
| 29/04/2000 | Maidstone United (P) | 3 | 2 | Lydd Town |
| 29/04/2000 | Sheerness East (P) | 1 | 0 | Knatchbull |
| 29/04/2000 | Snodland | 5 | 0 | Rye United |
| 29/04/2000 | Stansfield O&BC | 2 | 1 | Sevenoaks Town |
| 26/04/2000 | Greenways | 2 | 1 | Sevenoaks Town |
| 24/04/2000 | Bearsted | 0 | 0 | Maidstone United (P) |
| 24/04/2000 | Crockenhill (R) | 1 | 1 | Sevenoaks Town |
| 24/04/2000 | Lydd Town | 2 | 3 | Rye United |
| 24/04/2000 | Sheerness East (P) | 2 | 1 | Milton Athletic |
| 24/04/2000 | Snodland | 2 | 0 | Thames Polytechnic |
| 22/04/2000 | Knatchbull | 3 | 0 | Aylesford PM |
| 22/04/2000 | Sheerness East (P) | 2 | 1 | Rye United |
| 22/04/2000 | Snodland | 2 | 0 | Crockenhill (R) |
| 22/04/2000 | Thames Polytechnic | 1 | 5 | Bearsted |
| 19/04/2000 | Milton Athletic | 1 | 1 | Sevenoaks Town |
| 18/04/2000 | Sheerness East (P) | 2 | 1 | Aylesford PM |
| 15/04/2000 | Lydd Town | 3 | 2 | Snodland |
| 15/04/2000 | Maidstone United (P) | 2 | 1 | Sevenoaks Town |
| 15/04/2000 | Milton Athletic | 0 | 2 | Stansfield O&BC |
| 15/04/2000 | Rye United | 2 | 1 | Knatchbull |
| 11/04/2000 | Bearsted | 6 | 0 | Aylesford PM |
| 08/04/2000 | Crockenhill (R) | 1 | 1 | Milton Athletic |
| 08/04/2000 | Greenways | 0 | 2 | Maidstone United (P) |
| 08/04/2000 | Knatchbull | 0 | 0 | Bearsted |
| 08/04/2000 | Rye United | 6 | 1 | Lydd Town |
| 08/04/2000 | Snodland | 1 | 0 | Sheerness East (P) |
| 08/04/2000 | Thames Polytechnic | 2 | 1 | Sevenoaks Town |
| 01/04/2000 | Aylesford PM | 1 | 2 | Maidstone United (P) |
| 01/04/2000 | Crockenhill (R) | 0 | 0 | Rye United |
| 01/04/2000 | Greenways | 1 | 3 | Sheerness East (P) |
| 01/04/2000 | Lydd Town | 0 | 3 | Thames Polytechnic |
| 01/04/2000 | Milton Athletic | 1 | 1 | Bearsted |
| 01/04/2000 | Sevenoaks Town | 0 | 2 | Knatchbull |
| 01/04/2000 | Stansfield O&BC | 1 | 1 | Snodland |
| 25/03/2000 | Greenways | 0 | 2 | Bearsted |
| 25/03/2000 | Lydd Town | 0 | 3 | Milton Athletic |
| 25/03/2000 | Rye United | 0 | 0 | Stansfield O&BC |
| 25/03/2000 | Sevenoaks Town | 4 | 1 | Aylesford PM |
| 25/03/2000 | Thames Polytechnic | 2 | 3 | Crockenhill (R) |
| 18/03/2000 | Bearsted | 0 | 0 | Milton Athletic |
| 18/03/2000 | Greenways | 3 | 0 | Aylesford PM |
| 18/03/2000 | Knatchbull | 0 | 5 | Snodland |
| 18/03/2000 | Maidstone United (P) | 2 | 1 | Sheerness East (P) |
| 18/03/2000 | Stansfield O&BC | 5 | 1 | Lydd Town |
| 18/03/2000 | Thames Polytechnic | 1 | 2 | Rye United |
| 11/03/2000 | Aylesford PM | 0 | 6 | Stansfield O&BC |
| 11/03/2000 | Knatchbull | 4 | 2 | Lydd Town |
| 11/03/2000 | Rye United | 5 | 2 | Crockenhill (R) |
| 11/03/2000 | Sevenoaks Town | 0 | 0 | Maidstone United (P) |
| 11/03/2000 | Snodland | 0 | 0 | Greenways |
| 11/03/2000 | Thames Polytechnic | 4 | 0 | Sheerness East (P) |
| 04/03/2000 | Aylesford PM | 1 | 3 | Snodland |
| 04/03/2000 | Greenways | 3 | 2 | Knatchbull |
| 04/03/2000 | Lydd Town | 3 | 1 | Crockenhill (R) |
| 04/03/2000 | Milton Athletic | 4 | 2 | Rye United |
| 04/03/2000 | Thames Polytechnic | 1 | 2 | Stansfield O&BC |
| 26/02/2000 | Aylesford PM | 1 | 2 | Thames Polytechnic |
| 26/02/2000 | Crockenhill (R) | 1 | 3 | Bearsted |
| 26/02/2000 | Lydd Town | 2 | 0 | Greenways |
| 26/02/2000 | Sevenoaks Town | 1 | 5 | Milton Athletic |
| 26/02/2000 | Sheerness East (P) | 0 | 1 | Stansfield O&BC |
| 26/02/2000 | Snodland | 3 | 1 | Knatchbull |
| 19/02/2000 | Maidstone United (P) | 3 | 1 | Crockenhill (R) |
| 19/02/2000 | Milton Athletic | 1 | 1 | Knatchbull |
| 19/02/2000 | Stansfield O&BC | 2 | 1 | Thames Polytechnic |
| 12/02/2000 | Crockenhill (R) | 1 | 3 | Thames Polytechnic |
| 05/02/2000 | Aylesford PM | 1 | 4 | Rye United |
| 05/02/2000 | Bearsted | 1 | 0 | Lydd Town |
| 05/02/2000 | Greenways | 3 | 2 | Crockenhill (R) |
| 05/02/2000 | Maidstone United (P) | 1 | 2 | Thames Polytechnic |
| 05/02/2000 | Milton Athletic | 2 | 2 | Snodland |
| 05/02/2000 | Sevenoaks Town | 1 | 0 | Sheerness East (P) |
| 05/02/2000 | Stansfield O&BC | 1 | 3 | Knatchbull |
| 29/01/2000 | Crockenhill (R) | 2 | 0 | Maidstone United (P) |
| 29/01/2000 | Lydd Town | 4 | 2 | Aylesford PM |
| 29/01/2000 | Rye United | 0 | 3 | Sevenoaks Town |
| 29/01/2000 | Snodland | 2 | 1 | Stansfield O&BC |
| 22/01/2000 | Aylesford PM | 2 | 1 | Lydd Town |
| 22/01/2000 | Greenways | 0 | 3 | Snodland |
| 22/01/2000 | Knatchbull | 5 | 0 | Sheerness East (P) |
| 22/01/2000 | Sevenoaks Town | 5 | 3 | Crockenhill (R) |
| 22/01/2000 | Stansfield O&BC | 0 | 0 | Rye United |
| 15/01/2000 | Aylesford PM | 0 | 4 | Bearsted |
| 15/01/2000 | Rye United | 2 | 1 | Maidstone United (P) |
| 15/01/2000 | Thames Polytechnic | 1 | 2 | Greenways |
| 08/01/2000 | Crockenhill (R) | 0 | 1 | Stansfield O&BC |
| 08/01/2000 | Greenways | 0 | 4 | Thames Polytechnic |
| 08/01/2000 | Rye United | 3 | 1 | Aylesford PM |
| 18/12/1999 | Crockenhill (R) | 1 | 2 | Lydd Town |
| 18/12/1999 | Maidstone United (P) | 0 | 2 | Snodland |
| 18/12/1999 | Milton Athletic | 2 | 1 | Greenways |
| 18/12/1999 | Thames Polytechnic | 1 | 5 | Knatchbull |
| 11/12/1999 | Maidstone United (P) | 3 | 0 | Knatchbull |
| 11/12/1999 | Rye United | 2 | 3 | Bearsted |
| 11/12/1999 | Sheerness East (P) | 2 | 6 | Crockenhill (R) |
| 11/12/1999 | Stansfield O&BC | 3 | 1 | Milton Athletic |
| 04/12/1999 | Aylesford PM | 1 | 4 | Crockenhill (R) |
| 04/12/1999 | Greenways | 1 | 1 | Stansfield O&BC |
| 04/12/1999 | Lydd Town | 1 | 1 | Sevenoaks Town |
| 04/12/1999 | Sheerness East (P) | 0 | 1 | Maidstone United (P) |
| 20/11/1999 | Crockenhill (R) | 2 | 4 | Aylesford PM |
| 20/11/1999 | Milton Athletic | 4 | 2 | Sheerness East (P) |
| 20/11/1999 | Rye United | 0 | 3 | Greenways |
| 20/11/1999 | Sevenoaks Town | 6 | 0 | Thames Polytechnic |
| 20/11/1999 | Snodland | 3 | 1 | Maidstone United (P) |
| 20/11/1999 | Stansfield O&BC | 0 | 2 | Bearsted |
| 13/11/1999 | Bearsted | 3 | 0 | Rye United |
| 13/11/1999 | Knatchbull | 7 | 2 | Crockenhill (R) |
| 13/11/1999 | Thames Polytechnic | 3 | 0 | Milton Athletic |
| 06/11/1999 | Aylesford PM | 0 | 1 | Milton Athletic |
| 06/11/1999 | Crockenhill (R) | 5 | 2 | Sheerness East (P) |
| 06/11/1999 | Knatchbull | 3 | 0 | Greenways |
| 06/11/1999 | Lydd Town | 0 | 1 | Stansfield O&BC |
| 06/11/1999 | Maidstone United (P) | 2 | 3 | Bearsted |
| 06/11/1999 | Rye United | 3 | 0 | Thames Polytechnic |
| 06/11/1999 | Sevenoaks Town | 2 | 5 | Snodland |
| 30/10/1999 | Bearsted | 4 | 1 | Sheerness East (P) |
| 30/10/1999 | Knatchbull | 1 | 2 | Sevenoaks Town |
| 30/10/1999 | Snodland | 3 | 1 | Milton Athletic |
| 30/10/1999 | Stansfield O&BC | 2 | 1 | Greenways |
| 30/10/1999 | Thames Polytechnic | 2 | 3 | Maidstone United (P) |
| 23/10/1999 | Aylesford PM | 2 | 0 | Greenways |
| 23/10/1999 | Lydd Town | 3 | 0 | Knatchbull |
| 23/10/1999 | Maidstone United (P) | 2 | 0 | Stansfield O&BC |
| 23/10/1999 | Rye United | 4 | 0 | Milton Athletic |
| 23/10/1999 | Sevenoaks Town | 1 | 3 | Bearsted |
| 23/10/1999 | Sheerness East (P) | 2 | 2 | Snodland |
| 16/10/1999 | Knatchbull | 2 | 3 | Rye United |
| 16/10/1999 | Maidstone United (P) | 1 | 1 | Greenways |
| 16/10/1999 | Milton Athletic | 2 | 1 | Crockenhill (R) |
| 16/10/1999 | Stansfield O&BC | 0 | 1 | Sheerness East (P) |
| 16/10/1999 | Thames Polytechnic | 2 | 0 | Lydd Town |
| 09/10/1999 | Aylesford PM | 1 | 8 | Sevenoaks Town |
| 09/10/1999 | Lydd Town | 2 | 0 | Maidstone United (P) |
| 09/10/1999 | Rye United | 0 | 3 | Snodland |
| 09/10/1999 | Sheerness East (P) | 0 | 0 | Greenways |
| 02/10/1999 | Bearsted | 1 | 1 | Knatchbull |
| 02/10/1999 | Greenways | 3 | 4 | Rye United |
| 02/10/1999 | Milton Athletic | 1 | 2 | Lydd Town |
| 02/10/1999 | Sheerness East (P) | 0 | 1 | Thames Polytechnic |
| 02/10/1999 | Snodland | 5 | 0 | Aylesford PM |
| 02/10/1999 | Stansfield O&BC | 2 | 0 | Crockenhill (R) |
| 25/09/1999 | Aylesford PM | 2 | 11 | Knatchbull |
| 25/09/1999 | Crockenhill (R) | 0 | 1 | Snodland |
| 25/09/1999 | Lydd Town | 3 | 1 | Sheerness East (P) |
| 25/09/1999 | Maidstone United (P) | 3 | 0 | Milton Athletic |
| 25/09/1999 | Sevenoaks Town | 7 | 3 | Greenways |
| 18/09/1999 | Bearsted | 2 | 1 | Crockenhill (R) |
| 18/09/1999 | Greenways | 1 | 2 | Lydd Town |
| 18/09/1999 | Knatchbull | 3 | 1 | Thames Polytechnic |
| 18/09/1999 | Milton Athletic | 2 | 1 | Aylesford PM |
| 18/09/1999 | Rye United | 6 | 1 | Sheerness East (P) |
| 18/09/1999 | Snodland | 1 | 3 | Sevenoaks Town |
| 18/09/1999 | Stansfield O&BC | 0 | 1 | Maidstone United (P) |
| 11/09/1999 | Aylesford PM | 1 | 3 | Sheerness East (P) |
| 11/09/1999 | Crockenhill (R) | 2 | 5 | Knatchbull |
| 11/09/1999 | Greenways | 0 | 1 | Milton Athletic |
| 11/09/1999 | Lydd Town | 1 | 1 | Bearsted |
| 11/09/1999 | Maidstone United (P) | 3 | 2 | Rye United |
| 11/09/1999 | Sevenoaks Town | 2 | 1 | Stansfield O&BC |
| 11/09/1999 | Thames Polytechnic | 1 | 2 | Snodland |
| 04/09/1999 | Bearsted | 1 | 0 | Greenways |
| 04/09/1999 | Knatchbull | 0 | 2 | Maidstone United (P) |
| 04/09/1999 | Milton Athletic | 0 | 0 | Thames Polytechnic |
| 04/09/1999 | Sevenoaks Town | 2 | 1 | Rye United |
| 04/09/1999 | Snodland | 7 | 1 | Lydd Town |
| 04/09/1999 | Stansfield O&BC | 3 | 2 | Aylesford PM |
| 28/08/1999 | Bearsted | 1 | 1 | Snodland |
| 28/08/1999 | Crockenhill (R) | 0 | 1 | Greenways |
| 28/08/1999 | Knatchbull | 3 | 0 | Milton Athletic |
| 28/08/1999 | Maidstone United (P) | 7 | 0 | Aylesford PM |
| 28/08/1999 | Sheerness East (P) | 1 | 1 | Sevenoaks Town |