| 09 May 2009 | | Macknade v Tunbridge Wells Third XI | Selling Road, Faversham | Results |
| 09 May 2009 | | Blackheath Third XI v Chislehurst and West Kent | Royal Artillery Barracks, Woolwich | Results |
| 09 May 2009 | | Offham v Betteshanger Colliery Welfare | Church Road, Offham | Results |
| 09 May 2009 | | Old Brockleians v Farningham | Eltham Palace Road, Eltham | Results |
| 09 May 2009 | | Old Wilsonians v Bapchild | Hayes Hill, Hayes | Results |
| 16 May 2009 | | Bapchild v Blackheath Third XI | Radfield Hill, Bapchild | Results |
| 16 May 2009 | | Betteshanger Colliery Welfare v Old Wilsonians | Welfare Ground, Deal | Results |
| 16 May 2009 | | Chislehurst and West Kent v Old Brockleians | West Kent Cricket Club Ground, Chislehurst | Results |
| 16 May 2009 | | Farningham v Macknade | Horton Way, Farningham | Results |
| 16 May 2009 | | Tunbridge Wells Third XI v Offham | Upper Nevill Ground, Tunbridge Wells | Results |
| 23 May 2009 | | Betteshanger Colliery Welfare v Tunbridge Wells Third XI | Welfare Ground, Deal | Results |
| 23 May 2009 | | Blackheath Third XI v Farningham | Royal Artillery Barracks, Woolwich | Results |
| 23 May 2009 | | Offham v Bapchild | Church Road, Offham | Results |
| 23 May 2009 | | Old Brockleians v Macknade | Eltham Palace Road, Eltham | Results |
| 23 May 2009 | | Old Wilsonians v Chislehurst and West Kent | Hayes Hill, Hayes | Results |
| 30 May 2009 | | Bapchild v Betteshanger Colliery Welfare | Radfield Hill, Bapchild | Results |
| 30 May 2009 | | Macknade v Blackheath Third XI | Selling Road, Faversham | Results |
| 30 May 2009 | | Chislehurst and West Kent v Offham | West Kent Cricket Club Ground, Chislehurst | Results |
| 30 May 2009 | | Farningham v Old Wilsonians | Horton Way, Farningham | Results |
| 30 May 2009 | | Tunbridge Wells Third XI v Old Brockleians | Upper Nevill Ground, Tunbridge Wells | Results |
| 06 Jun 2009 | | Bapchild v Chislehurst and West Kent | Radfield Hill, Bapchild | Results |
| 06 Jun 2009 | | Betteshanger Colliery Welfare v Farningham | Welfare Ground, Deal | Results |
| 06 Jun 2009 | | Blackheath Third XI v Tunbridge Wells Third XI | Royal Artillery Barracks, Woolwich | Results |
| 06 Jun 2009 | | Offham v Macknade | Church Road, Offham | Results |
| 06 Jun 2009 | | Old Wilsonians v Old Brockleians | Hayes Hill, Hayes | Results |
| 13 Jun 2009 | | Macknade v Old Wilsonians | Selling Road, Faversham | Results |
| 13 Jun 2009 | | Chislehurst and West Kent v Betteshanger Colliery Welfare | West Kent Cricket Club Ground, Chislehurst | Results |
| 13 Jun 2009 | | Farningham v Offham | Horton Way, Farningham | Results |
| 13 Jun 2009 | | Old Brockleians v Blackheath Third XI | Eltham Palace Road, Eltham | Results |
| 25 May 2009 | | Tunbridge Wells Third XI v Bapchild | Upper Nevill Ground, Tunbridge Wells | Results |
| 20 Jun 2009 | | Macknade v Chislehurst and West Kent | Selling Road, Faversham | Results |
| 20 Jun 2009 | | Blackheath Third XI v Betteshanger Colliery Welfare | Royal Artillery Barracks, Woolwich | Results |
| 20 Jun 2009 | | Old Brockleians v Bapchild | Eltham Palace Road, Eltham | Results |
| 20 Jun 2009 | | Old Wilsonians v Offham | Hayes Hill, Hayes | Results |
| 31 Aug 2009 | | Tunbridge Wells Third XI v Farningham | Upper Nevill Ground, Tunbridge Wells | Results |
| 27 Jun 2009 | | Bapchild v Farningham | Radfield Hill, Bapchild | Results |
| 27 Jun 2009 | | Betteshanger Colliery Welfare v Macknade | Welfare Ground, Deal | Results |
| 27 Jun 2009 | | Chislehurst and West Kent v Tunbridge Wells Third XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 27 Jun 2009 | | Offham v Old Brockleians | Church Road, Offham | Results |
| 27 Jun 2009 | | Old Wilsonians v Blackheath Third XI | Hayes Hill, Hayes | Results |
| 04 Jul 2009 | | Macknade v Bapchild | Selling Road, Faversham | Results |
| 04 Jul 2009 | | Blackheath Third XI v Offham | Royal Artillery Barracks, Woolwich | Results |
| 04 Jul 2009 | | Farningham v Chislehurst and West Kent | Horton Way, Farningham | Results |
| 04 Jul 2009 | | Old Brockleians v Betteshanger Colliery Welfare | Eltham Palace Road, Eltham | Results |
| 04 Jul 2009 | | Tunbridge Wells Third XI v Old Wilsonians | Upper Nevill Ground, Tunbridge Wells | Results |
| 11 Jul 2009 | | Bapchild v Old Wilsonians | Radfield Hill, Bapchild | Results |
| 11 Jul 2009 | | Betteshanger Colliery Welfare v Offham | Welfare Ground, Deal | Results |
| 11 Jul 2009 | | Chislehurst and West Kent v Blackheath Third XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 11 Jul 2009 | | Farningham v Old Brockleians | Horton Way, Farningham | Results |
| 11 Jul 2009 | | Tunbridge Wells Third XI v Macknade | Upper Nevill Ground, Tunbridge Wells | Results |
| 18 Jul 2009 | | Macknade v Farningham | Selling Road, Faversham | Results |
| 18 Jul 2009 | | Blackheath Third XI v Bapchild | Royal Artillery Barracks, Woolwich | Results |
| 18 Jul 2009 | | Offham v Tunbridge Wells Third XI | Church Road, Offham | Results |
| 18 Jul 2009 | | Old Brockleians v Chislehurst and West Kent | Eltham Palace Road, Eltham | Results |
| 18 Jul 2009 | | Old Wilsonians v Betteshanger Colliery Welfare | Hayes Hill, Hayes | Results |
| 25 Jul 2009 | | Bapchild v Offham | Radfield Hill, Bapchild | Results |
| 25 Jul 2009 | | Macknade v Old Brockleians | Selling Road, Faversham | Results |
| 25 Jul 2009 | | Chislehurst and West Kent v Old Wilsonians | West Kent Cricket Club Ground, Chislehurst | Results |
| 25 Jul 2009 | | Farningham v Blackheath Third XI | Horton Way, Farningham | Results |
| 25 Jul 2009 | | Tunbridge Wells Third XI v Betteshanger Colliery Welfare | Upper Nevill Ground, Tunbridge Wells | Results |
| 01 Aug 2009 | | Betteshanger Colliery Welfare v Bapchild | Welfare Ground, Deal | Results |
| 01 Aug 2009 | | Blackheath Third XI v Macknade | Royal Artillery Barracks, Woolwich | Results |
| 01 Aug 2009 | | Offham v Chislehurst and West Kent | Church Road, Offham | Results |
| 01 Aug 2009 | | Old Brockleians v Tunbridge Wells Third XI | Eltham Palace Road, Eltham | Results |
| 01 Aug 2009 | | Old Wilsonians v Farningham | Hayes Hill, Hayes | Results |
| 08 Aug 2009 | | Macknade v Offham | Selling Road, Faversham | Results |
| 08 Aug 2009 | | Chislehurst and West Kent v Bapchild | West Kent Cricket Club Ground, Chislehurst | Results |
| 08 Aug 2009 | | Farningham v Betteshanger Colliery Welfare | Horton Way, Farningham | Results |
| 08 Aug 2009 | | Old Brockleians v Old Wilsonians | Eltham Palace Road, Eltham | Results |
| 08 Aug 2009 | | Tunbridge Wells Third XI v Blackheath Third XI | Upper Nevill Ground, Tunbridge Wells | Results |
| 15 Aug 2009 | | Bapchild v Tunbridge Wells Third XI | Radfield Hill, Bapchild | Results |
| 15 Aug 2009 | | Betteshanger Colliery Welfare v Chislehurst and West Kent | Welfare Ground, Deal | Results |
| 15 Aug 2009 | | Blackheath Third XI v Old Brockleians | Royal Artillery Barracks, Woolwich | Results |
| 15 Aug 2009 | | Offham v Farningham | Church Road, Offham | Results |
| 15 Aug 2009 | | Old Wilsonians v Macknade | Hayes Hill, Hayes | Results |
| 22 Aug 2009 | | Bapchild v Old Brockleians | Radfield Hill, Bapchild | Results |
| 22 Aug 2009 | | Betteshanger Colliery Welfare v Blackheath Third XI | Welfare Ground, Deal | Results |
| 22 Aug 2009 | | Chislehurst and West Kent v Macknade | West Kent Cricket Club Ground, Chislehurst | Results |
| 22 Aug 2009 | | Farningham v Tunbridge Wells Third XI | Horton Way, Farningham | Results |
| 22 Aug 2009 | | Offham v Old Wilsonians | Church Road, Offham | Results |
| 29 Aug 2009 | | Macknade v Betteshanger Colliery Welfare | Selling Road, Faversham | Results |
| 29 Aug 2009 | | Blackheath Third XI v Old Wilsonians | Royal Artillery Barracks, Woolwich | Results |
| 29 Aug 2009 | | Farningham v Bapchild | Horton Way, Farningham | Results |
| 29 Aug 2009 | | Old Brockleians v Offham | Eltham Palace Road, Eltham | Results |
| 29 Aug 2009 | | Tunbridge Wells Third XI v Chislehurst and West Kent | Upper Nevill Ground, Tunbridge Wells | Results |
| 05 Sep 2009 | | Bapchild v Macknade | Radfield Hill, Bapchild | Results |
| 05 Sep 2009 | | Betteshanger Colliery Welfare v Old Brockleians | Welfare Ground, Deal | Results |
| 05 Sep 2009 | | Chislehurst and West Kent v Farningham | West Kent Cricket Club Ground, Chislehurst | Results |
| 05 Sep 2009 | | Offham v Blackheath Third XI | Church Road, Offham | Results |
| 05 Sep 2009 | | Old Wilsonians v Tunbridge Wells Third XI | Hayes Hill, Hayes | Results |
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