| 09 May 2009 | | Catford Wanderers Second XI v Ashford Town Fourth XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 09 May 2009 | | Chislehurst and West Kent Second XI v Walmer Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 09 May 2009 | | Cowdrey Second XI v Sidcup Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 09 May 2009 | | Linden Park Second XI v Upchurch Second XI | Higher Common Ground, Tunbridge Wells | Results |
| 09 May 2009 | | Old Elthamians Second XI v Wickham Park Second XI | Foxbury Sports Ground, Chislehurst | Results |
| 16 May 2009 | | Ashford Town Fourth XI v Old Elthamians Second XI | Stacians Park Annex Ground, Ashford | Results |
| 16 May 2009 | | Sidcup Second XI v Catford Wanderers Second XI | Crescent Farm, Sidcup | Results |
| 16 May 2009 | | Upchurch Second XI v Cowdrey Second XI | Holywell Meadow, Upchurch | Results |
| 16 May 2009 | | Walmer Second XI v Linden Park Second XI | Hull Park Sports Club, Deal | Results |
| 16 May 2009 | | Wickham Park Second XI v Chislehurst and West Kent Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 23 May 2009 | | Ashford Town Fourth XI v Wickham Park Second XI | Stacians Park Annex Ground, Ashford | Results |
| 23 May 2009 | | Catford Wanderers Second XI v Cowdrey Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 23 May 2009 | | Chislehurst and West Kent Second XI v Upchurch Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 23 May 2009 | | Linden Park Second XI v Sidcup Second XI | Higher Common Ground, Tunbridge Wells | Results |
| 23 May 2009 | | Old Elthamians Second XI v Walmer Second XI | Foxbury Sports Ground, Chislehurst | Results |
| 30 May 2009 | | Cowdrey Second XI v Linden Park Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 30 May 2009 | | Sidcup Second XI v Chislehurst and West Kent Second XI | Crescent Farm, Sidcup | Results |
| 30 May 2009 | | Upchurch Second XI v Old Elthamians Second XI | Holywell Meadow, Upchurch | Results |
| 30 May 2009 | | Walmer Second XI v Ashford Town Fourth XI | Hull Park Sports Club, Deal | Results |
| 30 May 2009 | | Wickham Park Second XI v Catford Wanderers Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 06 Jun 2009 | | Ashford Town Fourth XI v Sidcup Second XI | Stacians Park Annex Ground, Ashford | Results |
| 06 Jun 2009 | | Catford Wanderers Second XI v Walmer Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 06 Jun 2009 | | Chislehurst and West Kent Second XI v Linden Park Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 06 Jun 2009 | | Old Elthamians Second XI v Cowdrey Second XI | Foxbury Sports Ground, Chislehurst | Results |
| 06 Jun 2009 | | Wickham Park Second XI v Upchurch Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 13 Jun 2009 | | Cowdrey Second XI v Chislehurst and West Kent Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 13 Jun 2009 | | Linden Park Second XI v Catford Wanderers Second XI | Higher Common Ground, Tunbridge Wells | Results |
| 13 Jun 2009 | | Sidcup Second XI v Old Elthamians Second XI | Crescent Farm, Sidcup | Results |
| 13 Jun 2009 | | Upchurch Second XI v Ashford Town Fourth XI | Holywell Meadow, Upchurch | Results |
| 13 Jun 2009 | | Walmer Second XI v Wickham Park Second XI | Hull Park Sports Club, Deal | Results |
| 20 Jun 2009 | | Chislehurst and West Kent Second XI v Ashford Town Fourth XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 20 Jun 2009 | | Cowdrey Second XI v Walmer Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 20 Jun 2009 | | Linden Park Second XI v Wickham Park Second XI | Higher Common Ground, Tunbridge Wells | Results |
| 20 Jun 2009 | | Old Elthamians Second XI v Catford Wanderers Second XI | Foxbury Sports Ground, Chislehurst | Results |
| 20 Jun 2009 | | Sidcup Second XI v Upchurch Second XI | Crescent Farm, Sidcup | Results |
| 27 Jun 2009 | | Ashford Town Fourth XI v Cowdrey Second XI | Stacians Park Annex Ground, Ashford | Results |
| 27 Jun 2009 | | Catford Wanderers Second XI v Chislehurst and West Kent Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 27 Jun 2009 | | Old Elthamians Second XI v Linden Park Second XI | Foxbury Sports Ground, Chislehurst | Results |
| 27 Jun 2009 | | Walmer Second XI v Upchurch Second XI | Hull Park Sports Club, Deal | Results |
| 27 Jun 2009 | | Wickham Park Second XI v Sidcup Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 04 Jul 2009 | | Chislehurst and West Kent Second XI v Old Elthamians Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 04 Jul 2009 | | Cowdrey Second XI v Wickham Park Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 04 Jul 2009 | | Linden Park Second XI v Ashford Town Fourth XI | Higher Common Ground, Tunbridge Wells | Results |
| 04 Jul 2009 | | Sidcup Second XI v Walmer Second XI | Crescent Farm, Sidcup | Results |
| 04 Jul 2009 | | Upchurch Second XI v Catford Wanderers Second XI | Holywell Meadow, Upchurch | Results |
| 11 Jul 2009 | | Ashford Town Fourth XI v Catford Wanderers Second XI | Stacians Park Annex Ground, Ashford | Results |
| 11 Jul 2009 | | Sidcup Second XI v Cowdrey Second XI | Crescent Farm, Sidcup | Results |
| 11 Jul 2009 | | Upchurch Second XI v Linden Park Second XI | Holywell Meadow, Upchurch | Results |
| 11 Jul 2009 | | Walmer Second XI v Chislehurst and West Kent Second XI | Hull Park Sports Club, Deal | Results |
| 11 Jul 2009 | | Wickham Park Second XI v Old Elthamians Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 18 Jul 2009 | | Catford Wanderers Second XI v Sidcup Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 18 Jul 2009 | | Chislehurst and West Kent Second XI v Wickham Park Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 18 Jul 2009 | | Cowdrey Second XI v Upchurch Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 18 Jul 2009 | | Linden Park Second XI v Walmer Second XI | Higher Common Ground, Tunbridge Wells | Results |
| 18 Jul 2009 | | Old Elthamians Second XI v Ashford Town Fourth XI | Foxbury Sports Ground, Chislehurst | Results |
| 25 Jul 2009 | | Cowdrey Second XI v Catford Wanderers Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 25 Jul 2009 | | Sidcup Second XI v Linden Park Second XI | Crescent Farm, Sidcup | Results |
| 25 Jul 2009 | | Upchurch Second XI v Chislehurst and West Kent Second XI | Holywell Meadow, Upchurch | Results |
| 25 Jul 2009 | | Walmer Second XI v Old Elthamians Second XI | Hull Park Sports Club, Deal | Results |
| 25 Jul 2009 | | Wickham Park Second XI v Ashford Town Fourth XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 01 Aug 2009 | | Ashford Town Fourth XI v Walmer Second XI | Stacians Park Annex Ground, Ashford | Results |
| 01 Aug 2009 | | Catford Wanderers Second XI v Wickham Park Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 01 Aug 2009 | | Chislehurst and West Kent Second XI v Sidcup Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 01 Aug 2009 | | Linden Park Second XI v Cowdrey Second XI | Higher Common Ground, Tunbridge Wells | Results |
| 01 Aug 2009 | | Old Elthamians Second XI v Upchurch Second XI | Foxbury Sports Ground, Chislehurst | Results |
| 08 Aug 2009 | | Cowdrey Second XI v Old Elthamians Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 08 Aug 2009 | | Linden Park Second XI v Chislehurst and West Kent Second XI | Higher Common Ground, Tunbridge Wells | Results |
| 08 Aug 2009 | | Sidcup Second XI v Ashford Town Fourth XI | Crescent Farm, Sidcup | Results |
| 08 Aug 2009 | | Upchurch Second XI v Wickham Park Second XI | Holywell Meadow, Upchurch | Results |
| 08 Aug 2009 | | Walmer Second XI v Catford Wanderers Second XI | Hull Park Sports Club, Deal | Results |
| 15 Aug 2009 | | Ashford Town Fourth XI v Upchurch Second XI | Stacians Park Annex Ground, Ashford | Results |
| 15 Aug 2009 | | Catford Wanderers Second XI v Linden Park Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 15 Aug 2009 | | Chislehurst and West Kent Second XI v Cowdrey Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 15 Aug 2009 | | Old Elthamians Second XI v Sidcup Second XI | Foxbury Sports Ground, Chislehurst | Results |
| 15 Aug 2009 | | Wickham Park Second XI v Walmer Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 22 Aug 2009 | | Ashford Town Fourth XI v Chislehurst and West Kent Second XI | Stacians Park Annex Ground, Ashford | Results |
| 22 Aug 2009 | | Catford Wanderers Second XI v Old Elthamians Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 22 Aug 2009 | | Upchurch Second XI v Sidcup Second XI | Holywell Meadow, Upchurch | Results |
| 22 Aug 2009 | | Walmer Second XI v Cowdrey Second XI | Hull Park Sports Club, Deal | Results |
| 22 Aug 2009 | | Wickham Park Second XI v Linden Park Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 29 Aug 2009 | | Chislehurst and West Kent Second XI v Catford Wanderers Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 29 Aug 2009 | | Cowdrey Second XI v Ashford Town Fourth XI | Swanmead Sports Ground, Tonbridge | Results |
| 29 Aug 2009 | | Linden Park Second XI v Old Elthamians Second XI | Higher Common Ground, Tunbridge Wells | Results |
| 29 Aug 2009 | | Sidcup Second XI v Wickham Park Second XI | Crescent Farm, Sidcup | Results |
| 29 Aug 2009 | | Upchurch Second XI v Walmer Second XI | Holywell Meadow, Upchurch | Results |
| 05 Sep 2009 | | Ashford Town Fourth XI v Linden Park Second XI | Stacians Park Annex Ground, Ashford | Results |
| 05 Sep 2009 | | Catford Wanderers Second XI v Upchurch Second XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 05 Sep 2009 | | Old Elthamians Second XI v Chislehurst and West Kent Second XI | Foxbury Sports Ground, Chislehurst | Results |
| 05 Sep 2009 | | Walmer Second XI v Sidcup Second XI | Hull Park Sports Club, Deal | Results |
| 05 Sep 2009 | | Wickham Park Second XI v Cowdrey Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
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