| 13 May 2000 | | Bexleyheath Second XI v Tenterden Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 13 May 2000 | | Canterbury Second XI v RACS Second XI | Polo Farm Sports Club, Canterbury | Results |
| 13 May 2000 | | CUACO Second XI v Hartley Country Club Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 13 May 2000 | | Halls Second XI v Harvel Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 13 May 2000 | | Holmesdale Second XI v Sydenham Second XI | Montreal Park, Sevenoaks | Results |
| 13 May 2000 | | HSBC Second XI v Catford Wanderers Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 13 May 2000 | | Lloyds Bank Second XI v Farningham Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 13 May 2000 | | Old Colfeians Second XI v Bromley Common Second XI | Horn Park, Lee | Results |
| 13 May 2000 | | Sidcup Second XI v Hythe Second XI | Crescent Farm, Sidcup | Results |
| 20 May 2000 | | CUACO Second XI v Old Colfeians Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 20 May 2000 | | Farningham Second XI v RACS Second XI | Horton Way, Farningham | Results |
| 20 May 2000 | | Hartley Country Club Second XI v Sidcup Second XI | Hartley Country Club Ground, Hartley | Results |
| 20 May 2000 | | Harvel Second XI v Bexleyheath Second XI | Desmond Wood Ground, Harvel | Results |
| 20 May 2000 | | Holmesdale Second XI v Canterbury Second XI | Montreal Park, Sevenoaks | Results |
| 20 May 2000 | | Hythe Second XI v Catford Wanderers Second XI | The Grove, Hythe | Results |
| 20 May 2000 | | Lloyds Bank Second XI v Halls Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 20 May 2000 | | Sydenham Second XI v HSBC Second XI | Cricket Lane, Beckenham | Results |
| 20 May 2000 | | Tenterden Second XI v Bromley Common Second XI | Morghew Park, Tenterden | Results |
| 27 May 2000 | | Bexleyheath Second XI v RACS Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 27 May 2000 | | Bromley Common Second XI v Sidcup Second XI | The Grove, Bromley | Results |
| 27 May 2000 | | Farningham Second XI v HSBC Second XI | Horton Way, Farningham | Results |
| 27 May 2000 | | Halls Second XI v Holmesdale Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 27 May 2000 | | Hartley Country Club Second XI v Sydenham Second XI | Hartley Country Club Ground, Hartley | Results |
| 27 May 2000 | | Harvel Second XI v Lloyds Bank Second XI | Desmond Wood Ground, Harvel | Results |
| 27 May 2000 | | Hythe Second XI v Canterbury Second XI | The Grove, Hythe | Results |
| 27 May 2000 | | Old Colfeians Second XI v Catford Wanderers Second XI | Horn Park, Lee | Results |
| 27 May 2000 | | Tenterden Second XI v CUACO Second XI | Morghew Park, Tenterden | Results |
| 03 Jun 2000 | | Bexleyheath Second XI v Hartley Country Club Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 03 Jun 2000 | | Bromley Common Second XI v Farningham Second XI | The Grove, Bromley | Results |
| 03 Jun 2000 | | Canterbury Second XI v CUACO Second XI | Polo Farm Sports Club, Canterbury | Results |
| 03 Jun 2000 | | Catford Wanderers Second XI v Tenterden Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 03 Jun 2000 | | Halls Second XI v Old Colfeians Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 03 Jun 2000 | | HSBC Second XI v Lloyds Bank Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 03 Jun 2000 | | Hythe Second XI v Harvel Second XI | The Grove, Hythe | Results |
| 03 Jun 2000 | | RACS Second XI v Holmesdale Second XI | Metrogas Sports Ground, New Eltham | Results |
| 03 Jun 2000 | | Sidcup Second XI v Sydenham Second XI | Crescent Farm, Sidcup | Results |
| 10 Jun 2000 | | Bromley Common Second XI v HSBC Second XI | The Grove, Bromley | Results |
| 10 Jun 2000 | | Canterbury Second XI v Bexleyheath Second XI | Polo Farm Sports Club, Canterbury | Results |
| 10 Jun 2000 | | Catford Wanderers Second XI v Lloyds Bank Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 10 Jun 2000 | | Farningham Second XI v Halls Second XI | Horton Way, Farningham | Results |
| 10 Jun 2000 | | Harvel Second XI v Sydenham Second XI | Desmond Wood Ground, Harvel | Results |
| 10 Jun 2000 | | Holmesdale Second XI v CUACO Second XI | Montreal Park, Sevenoaks | Results |
| 10 Jun 2000 | | Old Colfeians Second XI v Hythe Second XI | Horn Park, Lee | Results |
| 10 Jun 2000 | | RACS Second XI v Sidcup Second XI | Metrogas Sports Ground, New Eltham | Results |
| 10 Jun 2000 | | Tenterden Second XI v Hartley Country Club Second XI | Morghew Park, Tenterden | Results |
| 17 Jun 2000 | | CUACO Second XI v Hythe Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 17 Jun 2000 | | Halls Second XI v Bexleyheath Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 17 Jun 2000 | | Hartley Country Club Second XI v Bromley Common Second XI | Hartley Country Club Ground, Hartley | Results |
| 17 Jun 2000 | | Harvel Second XI v Farningham Second XI | Desmond Wood Ground, Harvel | Results |
| 17 Jun 2000 | | Holmesdale Second XI v Catford Wanderers Second XI | Montreal Park, Sevenoaks | Results |
| 17 Jun 2000 | | HSBC Second XI v Sidcup Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 17 Jun 2000 | | Lloyds Bank Second XI v Canterbury Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 17 Jun 2000 | | Old Colfeians Second XI v Tenterden Second XI | Horn Park, Lee | Results |
| 17 Jun 2000 | | Sydenham Second XI v RACS Second XI | Cricket Lane, Beckenham | Results |
| 24 Jun 2000 | | Bromley Common Second XI v Bexleyheath Second XI | The Grove, Bromley | Results |
| 24 Jun 2000 | | Catford Wanderers Second XI v Canterbury Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 24 Jun 2000 | | CUACO Second XI v Halls Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 24 Jun 2000 | | Farningham Second XI v Sidcup Second XI | Horton Way, Farningham | Results |
| 24 Jun 2000 | | Hartley Country Club Second XI v Lloyds Bank Second XI | Hartley Country Club Ground, Hartley | Results |
| 24 Jun 2000 | | Harvel Second XI v Old Colfeians Second XI | Desmond Wood Ground, Harvel | Results |
| 24 Jun 2000 | | Holmesdale Second XI v HSBC Second XI | Montreal Park, Sevenoaks | Results |
| 24 Jun 2000 | | Hythe Second XI v RACS Second XI | The Grove, Hythe | Results |
| 24 Jun 2000 | | Tenterden Second XI v Sydenham Second XI | Morghew Park, Tenterden | Results |
| 01 Jul 2000 | | Bexleyheath Second XI v Holmesdale Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 01 Jul 2000 | | Canterbury Second XI v Hartley Country Club Second XI | Polo Farm Sports Club, Canterbury | Results |
| 01 Jul 2000 | | Catford Wanderers Second XI v Bromley Common Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 01 Jul 2000 | | CUACO Second XI v Sidcup Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 01 Jul 2000 | | Farningham Second XI v Hythe Second XI | Horton Way, Farningham | Results |
| 01 Jul 2000 | | HSBC Second XI v Halls Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 01 Jul 2000 | | RACS Second XI v Harvel Second XI | Metrogas Sports Ground, New Eltham | Results |
| 01 Jul 2000 | | Sydenham Second XI v Old Colfeians Second XI | Cricket Lane, Beckenham | Results |
| 01 Jul 2000 | | Tenterden Second XI v Lloyds Bank Second XI | Morghew Park, Tenterden | Results |
| 08 Jul 2000 | | Bexleyheath Second XI v Catford Wanderers Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 08 Jul 2000 | | Canterbury Second XI v Farningham Second XI | Polo Farm Sports Club, Canterbury | Results |
| 08 Jul 2000 | | Halls Second XI v Sydenham Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 08 Jul 2000 | | HSBC Second XI v Hartley Country Club Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 08 Jul 2000 | | Hythe Second XI v Tenterden Second XI | The Grove, Hythe | Results |
| 08 Jul 2000 | | Lloyds Bank Second XI v CUACO Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 08 Jul 2000 | | Old Colfeians Second XI v Holmesdale Second XI | Horn Park, Lee | Results |
| 08 Jul 2000 | | RACS Second XI v Bromley Common Second XI | Metrogas Sports Ground, New Eltham | Results |
| 08 Jul 2000 | | Sidcup Second XI v Harvel Second XI | Crescent Farm, Sidcup | Results |
| 15 Jul 2000 | | Catford Wanderers Second XI v Halls Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 15 Jul 2000 | | CUACO Second XI v Harvel Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 15 Jul 2000 | | Hartley Country Club Second XI v Holmesdale Second XI | Hartley Country Club Ground, Hartley | Results |
| 15 Jul 2000 | | HSBC Second XI v Hythe Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 15 Jul 2000 | | Lloyds Bank Second XI v Bromley Common Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 15 Jul 2000 | | Old Colfeians Second XI v RACS Second XI | Horn Park, Lee | Results |
| 15 Jul 2000 | | Sidcup Second XI v Bexleyheath Second XI | Crescent Farm, Sidcup | Results |
| 15 Jul 2000 | | Sydenham Second XI v Farningham Second XI | Cricket Lane, Beckenham | Results |
| 15 Jul 2000 | | Tenterden Second XI v Canterbury Second XI | Morghew Park, Tenterden | Results |
| 22 Jul 2000 | | CUACO Second XI v Bexleyheath Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 22 Jul 2000 | | Farningham Second XI v Catford Wanderers Second XI | Horton Way, Farningham | Results |
| 22 Jul 2000 | | Halls Second XI v Sidcup Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 22 Jul 2000 | | Harvel Second XI v Bromley Common Second XI | Desmond Wood Ground, Harvel | Results |
| 22 Jul 2000 | | Holmesdale Second XI v Hythe Second XI | Montreal Park, Sevenoaks | Results |
| 22 Jul 2000 | | HSBC Second XI v Tenterden Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 22 Jul 2000 | | Lloyds Bank Second XI v Old Colfeians Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 22 Jul 2000 | | RACS Second XI v Hartley Country Club Second XI | Metrogas Sports Ground, New Eltham | Results |
| 22 Jul 2000 | | Sydenham Second XI v Canterbury Second XI | Cricket Lane, Beckenham | Results |
| 29 Jul 2000 | | Bexleyheath Second XI v Old Colfeians Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 29 Jul 2000 | | Bromley Common Second XI v Halls Second XI | The Grove, Bromley | Results |
| 29 Jul 2000 | | Catford Wanderers Second XI v Sydenham Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 29 Jul 2000 | | Farningham Second XI v CUACO Second XI | Horton Way, Farningham | Results |
| 29 Jul 2000 | | Harvel Second XI v Hartley Country Club Second XI | Desmond Wood Ground, Harvel | Results |
| 29 Jul 2000 | | Hythe Second XI v Lloyds Bank Second XI | The Grove, Hythe | Results |
| 29 Jul 2000 | | RACS Second XI v HSBC Second XI | Metrogas Sports Ground, New Eltham | Results |
| 29 Jul 2000 | | Sidcup Second XI v Canterbury Second XI | Crescent Farm, Sidcup | Results |
| 29 Jul 2000 | | Tenterden Second XI v Holmesdale Second XI | Morghew Park, Tenterden | Results |
| 05 Aug 2000 | | Bexleyheath Second XI v Lloyds Bank Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 05 Aug 2000 | | Bromley Common Second XI v CUACO Second XI | The Grove, Bromley | Results |
| 05 Aug 2000 | | Canterbury Second XI v HSBC Second XI | Polo Farm Sports Club, Canterbury | Results |
| 05 Aug 2000 | | Catford Wanderers Second XI v Hartley Country Club Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 05 Aug 2000 | | Harvel Second XI v Tenterden Second XI | Desmond Wood Ground, Harvel | Results |
| 05 Aug 2000 | | Holmesdale Second XI v Farningham Second XI | Montreal Park, Sevenoaks | Results |
| 05 Aug 2000 | | Hythe Second XI v Sydenham Second XI | The Grove, Hythe | Results |
| 05 Aug 2000 | | RACS Second XI v Halls Second XI | Metrogas Sports Ground, New Eltham | Results |
| 05 Aug 2000 | | Sidcup Second XI v Old Colfeians Second XI | Crescent Farm, Sidcup | Results |
| 12 Aug 2000 | | Bexleyheath Second XI v Sydenham Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 12 Aug 2000 | | Bromley Common Second XI v Holmesdale Second XI | The Grove, Bromley | Results |
| 12 Aug 2000 | | Catford Wanderers Second XI v Harvel Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 12 Aug 2000 | | CUACO Second XI v RACS Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 12 Aug 2000 | | Farningham Second XI v Tenterden Second XI | Horton Way, Farningham | Results |
| 12 Aug 2000 | | Halls Second XI v Canterbury Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 12 Aug 2000 | | Hartley Country Club Second XI v Hythe Second XI | Hartley Country Club Ground, Hartley | Results |
| 12 Aug 2000 | | Old Colfeians Second XI v HSBC Second XI | Horn Park, Lee | Results |
| 12 Aug 2000 | | Sidcup Second XI v Lloyds Bank Second XI | Crescent Farm, Sidcup | Results |
| 19 Aug 2000 | | Canterbury Second XI v Old Colfeians Second XI | Polo Farm Sports Club, Canterbury | Results |
| 19 Aug 2000 | | CUACO Second XI v Catford Wanderers Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 19 Aug 2000 | | Halls Second XI v Hythe Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 19 Aug 2000 | | Hartley Country Club Second XI v Farningham Second XI | Hartley Country Club Ground, Hartley | Results |
| 19 Aug 2000 | | Holmesdale Second XI v Harvel Second XI | Montreal Park, Sevenoaks | Results |
| 19 Aug 2000 | | HSBC Second XI v Bexleyheath Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 19 Aug 2000 | | Lloyds Bank Second XI v RACS Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 19 Aug 2000 | | Sydenham Second XI v Bromley Common Second XI | Cricket Lane, Beckenham | Results |
| 19 Aug 2000 | | Tenterden Second XI v Sidcup Second XI | Morghew Park, Tenterden | Results |
| 26 Aug 2000 | | Canterbury Second XI v Bromley Common Second XI | Polo Farm Sports Club, Canterbury | Results |
| 26 Aug 2000 | | Halls Second XI v Hartley Country Club Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 26 Aug 2000 | | HSBC Second XI v Harvel Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 26 Aug 2000 | | Hythe Second XI v Bexleyheath Second XI | The Grove, Hythe | Results |
| 26 Aug 2000 | | Lloyds Bank Second XI v Holmesdale Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 26 Aug 2000 | | Old Colfeians Second XI v Farningham Second XI | Horn Park, Lee | Results |
| 26 Aug 2000 | | RACS Second XI v Tenterden Second XI | Metrogas Sports Ground, New Eltham | Results |
| 26 Aug 2000 | | Sidcup Second XI v Catford Wanderers Second XI | Crescent Farm, Sidcup | Results |
| 26 Aug 2000 | | Sydenham Second XI v CUACO Second XI | Cricket Lane, Beckenham | Results |
| 02 Sep 2000 | | Bromley Common Second XI v Hythe Second XI | The Grove, Bromley | Results |
| 02 Sep 2000 | | Catford Wanderers Second XI v RACS Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 02 Sep 2000 | | CUACO Second XI v HSBC Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 02 Sep 2000 | | Farningham Second XI v Bexleyheath Second XI | Horton Way, Farningham | Results |
| 02 Sep 2000 | | Halls Second XI v Tenterden Second XI | Princes Golf and Leisure Club Ground, Dartford | Results |
| 02 Sep 2000 | | Hartley Country Club Second XI v Old Colfeians Second XI | Hartley Country Club Ground, Hartley | Results |
| 02 Sep 2000 | | Harvel Second XI v Canterbury Second XI | Desmond Wood Ground, Harvel | Results |
| 02 Sep 2000 | | Holmesdale Second XI v Sidcup Second XI | Montreal Park, Sevenoaks | Results |
| 02 Sep 2000 | | Sydenham Second XI v Lloyds Bank Second XI | Cricket Lane, Beckenham | Results |
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