| 08 May 1999 | | Beverley Second XI v Sidcup Second XI | Polo Farm Sports Club, Canterbury | Results |
| 08 May 1999 | | Catford Wanderers Second XI v Broadstairs Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 08 May 1999 | | Dover Second XI v Hartley Country Club Second XI | Crabble Athletic Ground, Dover | Results |
| 08 May 1999 | | Farningham Second XI v CUACO Second XI | Horton Way, Farningham | Results |
| 08 May 1999 | | Hythe Second XI v Harvel Second XI | The Grove, Hythe | Results |
| 08 May 1999 | | Midland Bank Second XI v Old Colfeians Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 08 May 1999 | | Sydenham Second XI v Lloyds Bank Second XI | Cricket Lane, Beckenham | Results |
| 08 May 1999 | | Walmer Second XI v RACS Second XI | Hull Park Sports Club, Deal | Results |
| 08 May 1999 | | Whitstable Second XI v Bexleyheath Second XI | Belmont Road, Whitstable | Results |
| 15 May 1999 | | Catford Wanderers Second XI v Midland Bank Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 15 May 1999 | | CUACO Second XI v Beverley Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 15 May 1999 | | Hartley Country Club Second XI v Walmer Second XI | Hartley Country Club Ground, Hartley | Results |
| 15 May 1999 | | Harvel Second XI v Bexleyheath Second XI | Desmond Wood Ground, Harvel | Results |
| 15 May 1999 | | Old Colfeians Second XI v Broadstairs Second XI | Horn Park, Lee | Results |
| 15 May 1999 | | RACS Second XI v Dover Second XI | Metrogas Sports Ground, New Eltham | Results |
| 15 May 1999 | | Sidcup Second XI v Farningham Second XI | Crescent Farm, Sidcup | Results |
| 15 May 1999 | | Whitstable Second XI v Hythe Second XI | Belmont Road, Whitstable | Results |
| 22 May 1999 | | Bexleyheath Second XI v Beverley Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 22 May 1999 | | Dover Second XI v Sidcup Second XI | Crabble Athletic Ground, Dover | Results |
| 22 May 1999 | | Hartley Country Club Second XI v Old Colfeians Second XI | Hartley Country Club Ground, Hartley | Results |
| 22 May 1999 | | Hythe Second XI v Farningham Second XI | The Grove, Hythe | Results |
| 22 May 1999 | | Lloyds Bank Second XI v Whitstable Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 22 May 1999 | | RACS Second XI v Catford Wanderers Second XI | Metrogas Sports Ground, New Eltham | Results |
| 22 May 1999 | | Sydenham Second XI v Harvel Second XI | Cricket Lane, Beckenham | Results |
| 22 May 1999 | | Walmer Second XI v CUACO Second XI | Hull Park Sports Club, Deal | Results |
| 29 May 1999 | | Beverley Second XI v Hythe Second XI | Polo Farm Sports Club, Canterbury | Results |
| 29 May 1999 | | Bexleyheath Second XI v Farningham Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 29 May 1999 | | Dover Second XI v CUACO Second XI | Crabble Athletic Ground, Dover | Results |
| 29 May 1999 | | Hartley Country Club Second XI v Catford Wanderers Second XI | Hartley Country Club Ground, Hartley | Results |
| 29 May 1999 | | Harvel Second XI v Lloyds Bank Second XI | Desmond Wood Ground, Harvel | Results |
| 29 May 1999 | | Midland Bank Second XI v Broadstairs Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 29 May 1999 | | Old Colfeians Second XI v RACS Second XI | Horn Park, Lee | Results |
| 29 May 1999 | | Sidcup Second XI v Walmer Second XI | Crescent Farm, Sidcup | Results |
| 29 May 1999 | | Sydenham Second XI v Whitstable Second XI | Cricket Lane, Beckenham | Results |
| 05 Jun 1999 | | Bexleyheath Second XI v Hartley Country Club Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 05 Jun 1999 | | Broadstairs Second XI v Sydenham Second XI | Park Avenue, Dumpton Park | Results |
| 05 Jun 1999 | | Dover Second XI v Catford Wanderers Second XI | Crabble Athletic Ground, Dover | Results |
| 05 Jun 1999 | | Farningham Second XI v Whitstable Second XI | Horton Way, Farningham | Results |
| 05 Jun 1999 | | Harvel Second XI v Beverley Second XI | Desmond Wood Ground, Harvel | Results |
| 05 Jun 1999 | | Lloyds Bank Second XI v Midland Bank Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 05 Jun 1999 | | Old Colfeians Second XI v Walmer Second XI | Horn Park, Lee | Results |
| 05 Jun 1999 | | RACS Second XI v Hythe Second XI | Metrogas Sports Ground, New Eltham | Results |
| 05 Jun 1999 | | Sidcup Second XI v CUACO Second XI | Crescent Farm, Sidcup | Results |
| 12 Jun 1999 | | Beverley Second XI v Whitstable Second XI | Polo Farm Sports Club, Canterbury | Results |
| 12 Jun 1999 | | Bexleyheath Second XI v RACS Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 12 Jun 1999 | | Broadstairs Second XI v Lloyds Bank Second XI | Park Avenue, Dumpton Park | Results |
| 12 Jun 1999 | | Dover Second XI v Old Colfeians Second XI | Crabble Athletic Ground, Dover | Results |
| 12 Jun 1999 | | Farningham Second XI v Harvel Second XI | Horton Way, Farningham | Results |
| 12 Jun 1999 | | Hythe Second XI v Hartley Country Club Second XI | The Grove, Hythe | Results |
| 12 Jun 1999 | | Midland Bank Second XI v Sydenham Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 12 Jun 1999 | | Walmer Second XI v Catford Wanderers Second XI | Hull Park Sports Club, Deal | Results |
| 19 Jun 1999 | | Broadstairs Second XI v Walmer Second XI | Park Avenue, Dumpton Park | Results |
| 19 Jun 1999 | | Catford Wanderers Second XI v Hythe Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 19 Jun 1999 | | CUACO Second XI v Lloyds Bank Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 19 Jun 1999 | | Harvel Second XI v Hartley Country Club Second XI | Desmond Wood Ground, Harvel | Results |
| 19 Jun 1999 | | Midland Bank Second XI v Dover Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 19 Jun 1999 | | Old Colfeians Second XI v Bexleyheath Second XI | Horn Park, Lee | Results |
| 19 Jun 1999 | | Sidcup Second XI v Sydenham Second XI | Crescent Farm, Sidcup | Results |
| 19 Jun 1999 | | Whitstable Second XI v RACS Second XI | Belmont Road, Whitstable | Results |
| 26 Jun 1999 | | Broadstairs Second XI v Dover Second XI | Park Avenue, Dumpton Park | Results |
| 26 Jun 1999 | | Catford Wanderers Second XI v Bexleyheath Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 26 Jun 1999 | | CUACO Second XI v Sydenham Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 26 Jun 1999 | | Farningham Second XI v Beverley Second XI | Horton Way, Farningham | Results |
| 26 Jun 1999 | | Hythe Second XI v Old Colfeians Second XI | The Grove, Hythe | Results |
| 26 Jun 1999 | | Lloyds Bank Second XI v Sidcup Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 26 Jun 1999 | | RACS Second XI v Harvel Second XI | Metrogas Sports Ground, New Eltham | Results |
| 26 Jun 1999 | | Walmer Second XI v Midland Bank Second XI | Hull Park Sports Club, Deal | Results |
| 26 Jun 1999 | | Whitstable Second XI v Hartley Country Club Second XI | Belmont Road, Whitstable | Results |
| 03 Jul 1999 | | Beverley Second XI v Lloyds Bank Second XI | Polo Farm Sports Club, Canterbury | Results |
| 03 Jul 1999 | | Bexleyheath Second XI v Dover Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 03 Jul 1999 | | CUACO Second XI v Catford Wanderers Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 03 Jul 1999 | | Hartley Country Club Second XI v Broadstairs Second XI | Hartley Country Club Ground, Hartley | Results |
| 03 Jul 1999 | | Harvel Second XI v Whitstable Second XI | Desmond Wood Ground, Harvel | Results |
| 03 Jul 1999 | | Midland Bank Second XI v RACS Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 03 Jul 1999 | | Old Colfeians Second XI v Sidcup Second XI | Horn Park, Lee | Results |
| 03 Jul 1999 | | Sydenham Second XI v Farningham Second XI | Cricket Lane, Beckenham | Results |
| 03 Jul 1999 | | Walmer Second XI v Hythe Second XI | Hull Park Sports Club, Deal | Results |
| 10 Jul 1999 | | Bexleyheath Second XI v Walmer Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 10 Jul 1999 | | CUACO Second XI v Old Colfeians Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 10 Jul 1999 | | Hartley Country Club Second XI v Midland Bank Second XI | Hartley Country Club Ground, Hartley | Results |
| 10 Jul 1999 | | Hythe Second XI v Dover Second XI | The Grove, Hythe | Results |
| 10 Jul 1999 | | Lloyds Bank Second XI v Farningham Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 10 Jul 1999 | | RACS Second XI v Broadstairs Second XI | Metrogas Sports Ground, New Eltham | Results |
| 10 Jul 1999 | | Sidcup Second XI v Catford Wanderers Second XI | Crescent Farm, Sidcup | Results |
| 10 Jul 1999 | | Sydenham Second XI v Beverley Second XI | Cricket Lane, Beckenham | Results |
| 17 Jul 1999 | | Broadstairs Second XI v Hythe Second XI | Park Avenue, Dumpton Park | Results |
| 17 Jul 1999 | | Dover Second XI v Lloyds Bank Second XI | Crabble Athletic Ground, Dover | Results |
| 17 Jul 1999 | | Hartley Country Club Second XI v Beverley Second XI | Hartley Country Club Ground, Hartley | Results |
| 17 Jul 1999 | | Harvel Second XI v CUACO Second XI | Desmond Wood Ground, Harvel | Results |
| 17 Jul 1999 | | Midland Bank Second XI v Bexleyheath Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 17 Jul 1999 | | RACS Second XI v Farningham Second XI | Metrogas Sports Ground, New Eltham | Results |
| 17 Jul 1999 | | Walmer Second XI v Sydenham Second XI | Hull Park Sports Club, Deal | Results |
| 17 Jul 1999 | | Whitstable Second XI v Sidcup Second XI | Belmont Road, Whitstable | Results |
| 24 Jul 1999 | | Beverley Second XI v RACS Second XI | Polo Farm Sports Club, Canterbury | Results |
| 24 Jul 1999 | | Broadstairs Second XI v Bexleyheath Second XI | Park Avenue, Dumpton Park | Results |
| 24 Jul 1999 | | Dover Second XI v Sydenham Second XI | Crabble Athletic Ground, Dover | Results |
| 24 Jul 1999 | | Hartley Country Club Second XI v Farningham Second XI | Hartley Country Club Ground, Hartley | Results |
| 24 Jul 1999 | | Hythe Second XI v Midland Bank Second XI | The Grove, Hythe | Results |
| 24 Jul 1999 | | Lloyds Bank Second XI v Walmer Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 24 Jul 1999 | | Old Colfeians Second XI v Catford Wanderers Second XI | Horn Park, Lee | Results |
| 24 Jul 1999 | | Sidcup Second XI v Harvel Second XI | Crescent Farm, Sidcup | Results |
| 24 Jul 1999 | | Whitstable Second XI v CUACO Second XI | Belmont Road, Whitstable | Results |
| 31 Jul 1999 | | Beverley Second XI v Dover Second XI | Polo Farm Sports Club, Canterbury | Results |
| 31 Jul 1999 | | Catford Wanderers Second XI v Harvel Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 31 Jul 1999 | | CUACO Second XI v Midland Bank Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 31 Jul 1999 | | Farningham Second XI v Walmer Second XI | Horton Way, Farningham | Results |
| 31 Jul 1999 | | Lloyds Bank Second XI v Hartley Country Club Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 31 Jul 1999 | | Old Colfeians Second XI v Whitstable Second XI | Horn Park, Lee | Results |
| 31 Jul 1999 | | Sidcup Second XI v Broadstairs Second XI | Crescent Farm, Sidcup | Results |
| 31 Jul 1999 | | Sydenham Second XI v RACS Second XI | Cricket Lane, Beckenham | Results |
| 07 Aug 1999 | | Bexleyheath Second XI v Hythe Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 07 Aug 1999 | | Catford Wanderers Second XI v Whitstable Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 07 Aug 1999 | | CUACO Second XI v Broadstairs Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 07 Aug 1999 | | Farningham Second XI v Dover Second XI | Horton Way, Farningham | Results |
| 07 Aug 1999 | | Harvel Second XI v Old Colfeians Second XI | Desmond Wood Ground, Harvel | Results |
| 07 Aug 1999 | | Midland Bank Second XI v Sidcup Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 07 Aug 1999 | | RACS Second XI v Lloyds Bank Second XI | Metrogas Sports Ground, New Eltham | Results |
| 07 Aug 1999 | | Sydenham Second XI v Hartley Country Club Second XI | Cricket Lane, Beckenham | Results |
| 07 Aug 1999 | | Walmer Second XI v Beverley Second XI | Hull Park Sports Club, Deal | Results |
| 14 Aug 1999 | | Bexleyheath Second XI v Lloyds Bank Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 14 Aug 1999 | | Broadstairs Second XI v Harvel Second XI | Park Avenue, Dumpton Park | Results |
| 14 Aug 1999 | | Catford Wanderers Second XI v Beverley Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 14 Aug 1999 | | Hartley Country Club Second XI v Sidcup Second XI | Hartley Country Club Ground, Hartley | Results |
| 14 Aug 1999 | | Hythe Second XI v Sydenham Second XI | The Grove, Hythe | Results |
| 14 Aug 1999 | | Midland Bank Second XI v Whitstable Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 14 Aug 1999 | | Old Colfeians Second XI v Farningham Second XI | Horn Park, Lee | Results |
| 14 Aug 1999 | | RACS Second XI v CUACO Second XI | Metrogas Sports Ground, New Eltham | Results |
| 21 Aug 1999 | | Beverley Second XI v Old Colfeians Second XI | Polo Farm Sports Club, Canterbury | Results |
| 21 Aug 1999 | | Bexleyheath Second XI v Sydenham Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 21 Aug 1999 | | Broadstairs Second XI v Whitstable Second XI | Park Avenue, Dumpton Park | Results |
| 21 Aug 1999 | | Catford Wanderers Second XI v Farningham Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 21 Aug 1999 | | Dover Second XI v Walmer Second XI | Crabble Athletic Ground, Dover | Results |
| 21 Aug 1999 | | Hartley Country Club Second XI v CUACO Second XI | Hartley Country Club Ground, Hartley | Results |
| 21 Aug 1999 | | Harvel Second XI v Midland Bank Second XI | Desmond Wood Ground, Harvel | Results |
| 21 Aug 1999 | | Lloyds Bank Second XI v Hythe Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 21 Aug 1999 | | Sidcup Second XI v RACS Second XI | Crescent Farm, Sidcup | Results |
| 28 Aug 1999 | | Beverley Second XI v Broadstairs Second XI | Polo Farm Sports Club, Canterbury | Results |
| 28 Aug 1999 | | CUACO Second XI v Hythe Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 28 Aug 1999 | | Farningham Second XI v Midland Bank Second XI | Horton Way, Farningham | Results |
| 28 Aug 1999 | | Harvel Second XI v Dover Second XI | Desmond Wood Ground, Harvel | Results |
| 28 Aug 1999 | | Lloyds Bank Second XI v Catford Wanderers Second XI | The Kent County Cricket Ground, Beckenham | Results |
| 28 Aug 1999 | | Sidcup Second XI v Bexleyheath Second XI | Crescent Farm, Sidcup | Results |
| 28 Aug 1999 | | Sydenham Second XI v Old Colfeians Second XI | Cricket Lane, Beckenham | Results |
| 28 Aug 1999 | | Whitstable Second XI v Walmer Second XI | Belmont Road, Whitstable | Results |
| 04 Sep 1999 | | CUACO Second XI v Bexleyheath Second XI | National Westminster Bank Sports Ground, Beckenham | Results |
| 04 Sep 1999 | | Farningham Second XI v Broadstairs Second XI | Horton Way, Farningham | Results |
| 04 Sep 1999 | | Hythe Second XI v Sidcup Second XI | The Grove, Hythe | Results |
| 04 Sep 1999 | | Midland Bank Second XI v Beverley Second XI | HSBC Sports and Social Club, Beckenham | Results |
| 04 Sep 1999 | | Old Colfeians Second XI v Lloyds Bank Second XI | Horn Park, Lee | Results |
| 04 Sep 1999 | | RACS Second XI v Hartley Country Club Second XI | Metrogas Sports Ground, New Eltham | Results |
| 04 Sep 1999 | | Sydenham Second XI v Catford Wanderers Second XI | Cricket Lane, Beckenham | Results |
| 04 Sep 1999 | | Walmer Second XI v Harvel Second XI | Hull Park Sports Club, Deal | Results |
| 04 Sep 1999 | | Whitstable Second XI v Dover Second XI | Belmont Road, Whitstable | Results |
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