| 06 May 2000 | | Chestfield v Linden Park | Grasmere Road, Chestfield | Results |
| 06 May 2000 | | Dover v Bexleyheath | Crabble Athletic Ground, Dover | Results |
| 06 May 2000 | | Halls v Catford and Cyphers | Princes Golf and Leisure Club Ground, Dartford | Results |
| 06 May 2000 | | Old Dunstonians v Chislehurst and West Kent | St Dunstan's Lane, Beckenham | Results |
| 06 May 2000 | | Old Elthamians v Bapchild | Foxbury Sports Ground, Chislehurst | Results |
| 06 May 2000 | | Old Wilsonians v Macknade | Hayes Hill, Hayes | Results |
| 06 May 2000 | | Wye v Sibton Park | Horton Meadow, Wye | Results |
| 13 May 2000 | | Chislehurst and West Kent v Bapchild | West Kent Cricket Club Ground, Chislehurst | Results |
| 13 May 2000 | | Dover v CUACO | Crabble Athletic Ground, Dover | Results |
| 13 May 2000 | | Macknade v Bobbing Court | Selling Road, Faversham | Results |
| 13 May 2000 | | Old Dunstonians v Halls | St Dunstan's Lane, Beckenham | Results |
| 13 May 2000 | | Old Elthamians v Linden Park | Foxbury Sports Ground, Chislehurst | Results |
| 13 May 2000 | | Old Wilsonians v Bexleyheath | Hayes Hill, Hayes | Results |
| 13 May 2000 | | Sibton Park v Downham and Bellingham | Longage Hill, Lyminge | Results |
| 13 May 2000 | | Wye v Catford and Cyphers | Horton Meadow, Wye | Results |
| 20 May 2000 | | Bexleyheath v Macknade | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 20 May 2000 | | Chestfield v Bobbing Court | Grasmere Road, Chestfield | Results |
| 20 May 2000 | | Chislehurst and West Kent v Dover | West Kent Cricket Club Ground, Chislehurst | Results |
| 20 May 2000 | | Downham and Bellingham v Bapchild | Rangefield Road, Downham | Results |
| 20 May 2000 | | Linden Park v Wye | Higher Common Ground, Tunbridge Wells | Results |
| 20 May 2000 | | Old Dunstonians v Sibton Park | St Dunstan's Lane, Beckenham | Results |
| 20 May 2000 | | Old Elthamians v Old Wilsonians | Foxbury Sports Ground, Chislehurst | Results |
| 27 May 2000 | | Bapchild v Catford and Cyphers | Radfield Hill, Bapchild | Results |
| 27 May 2000 | | Chislehurst and West Kent v Bobbing Court | West Kent Cricket Club Ground, Chislehurst | Results |
| 27 May 2000 | | CUACO v Bexleyheath | National Westminster Bank Sports Ground, Beckenham | Results |
| 27 May 2000 | | Macknade v Chestfield | Selling Road, Faversham | Results |
| 27 May 2000 | | Old Wilsonians v Halls | Hayes Hill, Hayes | Results |
| 27 May 2000 | | Sibton Park v Linden Park | Longage Hill, Lyminge | Results |
| 27 May 2000 | | Wye v Dover | Horton Meadow, Wye | Results |
| 03 Jun 2000 | | Catford and Cyphers v Chislehurst and West Kent | Rubens Street Oval, Catford | Results |
| 03 Jun 2000 | | Chestfield v Bapchild | Grasmere Road, Chestfield | Results |
| 03 Jun 2000 | | CUACO v Linden Park | National Westminster Bank Sports Ground, Beckenham | Results |
| 03 Jun 2000 | | Dover v Macknade | Crabble Athletic Ground, Dover | Results |
| 03 Jun 2000 | | Downham and Bellingham v Wye | Rangefield Road, Downham | Results |
| 03 Jun 2000 | | Old Dunstonians v Old Elthamians | St Dunstan's Lane, Beckenham | Results |
| 03 Jun 2000 | | Sibton Park v Halls | Longage Hill, Lyminge | Results |
| 10 Jun 2000 | | Bapchild v Dover | Radfield Hill, Bapchild | Results |
| 10 Jun 2000 | | Bexleyheath v Wye | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 10 Jun 2000 | | Bobbing Court v Catford and Cyphers | Rook Lane, Bobbing | Results |
| 10 Jun 2000 | | Chislehurst and West Kent v Chestfield | West Kent Cricket Club Ground, Chislehurst | Results |
| 10 Jun 2000 | | CUACO v Halls | National Westminster Bank Sports Ground, Beckenham | Results |
| 10 Jun 2000 | | Macknade v Downham and Bellingham | Selling Road, Faversham | Results |
| 10 Jun 2000 | | Old Wilsonians v Old Dunstonians | Hayes Hill, Hayes | Results |
| 17 Jun 2000 | | Bexleyheath v Sibton Park | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 17 Jun 2000 | | Bobbing Court v Bapchild | Rook Lane, Bobbing | Results |
| 17 Jun 2000 | | Catford and Cyphers v Macknade | Rubens Street Oval, Catford | Results |
| 17 Jun 2000 | | Chestfield v Wye | Grasmere Road, Chestfield | Results |
| 17 Jun 2000 | | Downham and Bellingham v CUACO | Rangefield Road, Downham | Results |
| 17 Jun 2000 | | Linden Park v Old Wilsonians | Higher Common Ground, Tunbridge Wells | Results |
| 17 Jun 2000 | | Old Elthamians v Halls | Foxbury Sports Ground, Chislehurst | Results |
| 24 Jun 2000 | | Bexleyheath v Bapchild | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 24 Jun 2000 | | Bobbing Court v Dover | Rook Lane, Bobbing | Results |
| 24 Jun 2000 | | Catford and Cyphers v Chestfield | Rubens Street Oval, Catford | Results |
| 24 Jun 2000 | | Chislehurst and West Kent v Downham and Bellingham | West Kent Cricket Club Ground, Chislehurst | Results |
| 24 Jun 2000 | | Halls v Wye | Princes Golf and Leisure Club Ground, Dartford | Results |
| 24 Jun 2000 | | Macknade v Linden Park | Selling Road, Faversham | Results |
| 24 Jun 2000 | | Old Dunstonians v CUACO | St Dunstan's Lane, Beckenham | Results |
| 24 Jun 2000 | | Sibton Park v Old Elthamians | Longage Hill, Lyminge | Results |
| 01 Jul 2000 | | Bapchild v Old Dunstonians | Radfield Hill, Bapchild | Results |
| 01 Jul 2000 | | Catford and Cyphers v Linden Park | Rubens Street Oval, Catford | Results |
| 01 Jul 2000 | | Chestfield v Bexleyheath | Grasmere Road, Chestfield | Results |
| 01 Jul 2000 | | Dover v Downham and Bellingham | Crabble Athletic Ground, Dover | Results |
| 01 Jul 2000 | | Halls v Bobbing Court | Princes Golf and Leisure Club Ground, Dartford | Results |
| 01 Jul 2000 | | Macknade v Old Elthamians | Selling Road, Faversham | Results |
| 01 Jul 2000 | | Wye v Old Wilsonians | Horton Meadow, Wye | Results |
| 08 Jul 2000 | | Bapchild v Halls | Radfield Hill, Bapchild | Results |
| 08 Jul 2000 | | Bobbing Court v Bexleyheath | Rook Lane, Bobbing | Results |
| 08 Jul 2000 | | Catford and Cyphers v Downham and Bellingham | Rubens Street Oval, Catford | Results |
| 08 Jul 2000 | | Chestfield v Dover | Grasmere Road, Chestfield | Results |
| 08 Jul 2000 | | CUACO v Old Wilsonians | National Westminster Bank Sports Ground, Beckenham | Results |
| 08 Jul 2000 | | Linden Park v Chislehurst and West Kent | Higher Common Ground, Tunbridge Wells | Results |
| 08 Jul 2000 | | Wye v Old Dunstonians | Horton Meadow, Wye | Results |
| 15 Jul 2000 | | Bexleyheath v Catford and Cyphers | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 15 Jul 2000 | | Downham and Bellingham v Chestfield | Rangefield Road, Downham | Results |
| 15 Jul 2000 | | Halls v Chislehurst and West Kent | Princes Golf and Leisure Club Ground, Dartford | Results |
| 15 Jul 2000 | | Linden Park v Bobbing Court | Higher Common Ground, Tunbridge Wells | Results |
| 15 Jul 2000 | | Old Dunstonians v Macknade | St Dunstan's Lane, Beckenham | Results |
| 15 Jul 2000 | | Old Elthamians v Wye | Foxbury Sports Ground, Chislehurst | Results |
| 15 Jul 2000 | | Sibton Park v CUACO | Longage Hill, Lyminge | Results |
| 22 Jul 2000 | | Bexleyheath v Old Elthamians | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 22 Jul 2000 | | Bobbing Court v Wye | Rook Lane, Bobbing | Results |
| 22 Jul 2000 | | Chestfield v CUACO | Grasmere Road, Chestfield | Results |
| 22 Jul 2000 | | Chislehurst and West Kent v Macknade | West Kent Cricket Club Ground, Chislehurst | Results |
| 22 Jul 2000 | | Downham and Bellingham v Old Wilsonians | Rangefield Road, Downham | Results |
| 22 Jul 2000 | | Linden Park v Old Dunstonians | Higher Common Ground, Tunbridge Wells | Results |
| 22 Jul 2000 | | Sibton Park v Dover | Longage Hill, Lyminge | Results |
| 29 Jul 2000 | | Chislehurst and West Kent v Bexleyheath | West Kent Cricket Club Ground, Chislehurst | Results |
| 29 Jul 2000 | | CUACO v Old Elthamians | National Westminster Bank Sports Ground, Beckenham | Results |
| 29 Jul 2000 | | Dover v Catford and Cyphers | Crabble Athletic Ground, Dover | Results |
| 29 Jul 2000 | | Downham and Bellingham v Bobbing Court | Rangefield Road, Downham | Results |
| 29 Jul 2000 | | Halls v Macknade | Princes Golf and Leisure Club Ground, Dartford | Results |
| 29 Jul 2000 | | Linden Park v Bapchild | Higher Common Ground, Tunbridge Wells | Results |
| 29 Jul 2000 | | Old Wilsonians v Sibton Park | Hayes Hill, Hayes | Results |
| 05 Aug 2000 | | Bapchild v Old Wilsonians | Radfield Hill, Bapchild | Results |
| 05 Aug 2000 | | Bobbing Court v Old Dunstonians | Rook Lane, Bobbing | Results |
| 05 Aug 2000 | | CUACO v Wye | National Westminster Bank Sports Ground, Beckenham | Results |
| 05 Aug 2000 | | Dover v Linden Park | Crabble Athletic Ground, Dover | Results |
| 05 Aug 2000 | | Downham and Bellingham v Bexleyheath | Rangefield Road, Downham | Results |
| 05 Aug 2000 | | Halls v Chestfield | Princes Golf and Leisure Club Ground, Dartford | Results |
| 05 Aug 2000 | | Macknade v Sibton Park | Selling Road, Faversham | Results |
| 05 Aug 2000 | | Old Elthamians v Chislehurst and West Kent | Foxbury Sports Ground, Chislehurst | Results |
| 12 Aug 2000 | | Bapchild v Sibton Park | Radfield Hill, Bapchild | Results |
| 12 Aug 2000 | | Dover v Halls | Crabble Athletic Ground, Dover | Results |
| 12 Aug 2000 | | Linden Park v Downham and Bellingham | Higher Common Ground, Tunbridge Wells | Results |
| 12 Aug 2000 | | Macknade v CUACO | Selling Road, Faversham | Results |
| 12 Aug 2000 | | Old Dunstonians v Catford and Cyphers | St Dunstan's Lane, Beckenham | Results |
| 12 Aug 2000 | | Old Elthamians v Bobbing Court | Foxbury Sports Ground, Chislehurst | Results |
| 12 Aug 2000 | | Old Wilsonians v Chislehurst and West Kent | Hayes Hill, Hayes | Results |
| 19 Aug 2000 | | Bapchild v CUACO | Radfield Hill, Bapchild | Results |
| 19 Aug 2000 | | Bexleyheath v Linden Park | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 19 Aug 2000 | | Bobbing Court v Old Wilsonians | Rook Lane, Bobbing | Results |
| 19 Aug 2000 | | Catford and Cyphers v Old Elthamians | Rubens Street Oval, Catford | Results |
| 19 Aug 2000 | | Chestfield v Old Dunstonians | Grasmere Road, Chestfield | Results |
| 19 Aug 2000 | | Chislehurst and West Kent v Sibton Park | West Kent Cricket Club Ground, Chislehurst | Results |
| 19 Aug 2000 | | Downham and Bellingham v Halls | Rangefield Road, Downham | Results |
| 26 Aug 2000 | | Bexleyheath v Halls | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 26 Aug 2000 | | CUACO v Chislehurst and West Kent | National Westminster Bank Sports Ground, Beckenham | Results |
| 26 Aug 2000 | | Old Dunstonians v Dover | St Dunstan's Lane, Beckenham | Results |
| 26 Aug 2000 | | Old Elthamians v Chestfield | Foxbury Sports Ground, Chislehurst | Results |
| 26 Aug 2000 | | Old Wilsonians v Catford and Cyphers | Hayes Hill, Hayes | Results |
| 26 Aug 2000 | | Sibton Park v Bobbing Court | Longage Hill, Lyminge | Results |
| 26 Aug 2000 | | Wye v Macknade | Horton Meadow, Wye | Results |
| 02 Sep 2000 | | Bapchild v Wye | Radfield Hill, Bapchild | Results |
| 02 Sep 2000 | | Bobbing Court v CUACO | Rook Lane, Bobbing | Results |
| 02 Sep 2000 | | Catford and Cyphers v Sibton Park | Rubens Street Oval, Catford | Results |
| 02 Sep 2000 | | Chestfield v Old Wilsonians | Grasmere Road, Chestfield | Results |
| 02 Sep 2000 | | Dover v Old Elthamians | Crabble Athletic Ground, Dover | Results |
| 02 Sep 2000 | | Downham and Bellingham v Old Dunstonians | Rangefield Road, Downham | Results |
| 02 Sep 2000 | | Linden Park v Halls | Higher Common Ground, Tunbridge Wells | Results |
| 09 Sep 2000 | | CUACO v Catford and Cyphers | National Westminster Bank Sports Ground, Beckenham | Results |
| 09 Sep 2000 | | Macknade v Bapchild | Selling Road, Faversham | Results |
| 09 Sep 2000 | | Old Dunstonians v Bexleyheath | St Dunstan's Lane, Beckenham | Results |
| 09 Sep 2000 | | Old Elthamians v Downham and Bellingham | Foxbury Sports Ground, Chislehurst | Results |
| 09 Sep 2000 | | Old Wilsonians v Dover | Hayes Hill, Hayes | Results |
| 09 Sep 2000 | | Sibton Park v Chestfield | Longage Hill, Lyminge | Results |
| 09 Sep 2000 | | Wye v Chislehurst and West Kent | Horton Meadow, Wye | Results |
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