| 09 May 2009 | | Ashford Town Third XI v Addington Village | Stacians Park Annex Ground, Ashford | Results |
| 09 May 2009 | | Bromley Town v Rainham | Hayes Lane Cricket Ground, Bromley | Results |
| 09 May 2009 | | Rodmersham v Old Elthamians | Bottles Lane, Rodmersham Green | Results |
| 09 May 2009 | | Sidcup v Bexleyheath | Crescent Farm, Sidcup | Results |
| 09 May 2009 | | Walmer v Gravesend RF | Hull Park Sports Club, Deal | Results |
| 16 May 2009 | | Addington Village v Sidcup | Park Road, Addington | Results |
| 16 May 2009 | | Bexleyheath v Bromley Town | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 16 May 2009 | | Gravesend RF v Rodmersham | Rectory Field, Gravesend | Results |
| 16 May 2009 | | Old Elthamians v Ashford Town Third XI | Foxbury Sports Ground, Chislehurst | Results |
| 16 May 2009 | | Rainham v Walmer | Berengrave Park, Rainham | Results |
| 23 May 2009 | | Bexleyheath v Addington Village | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 23 May 2009 | | Bromley Town v Gravesend RF | Hayes Lane Cricket Ground, Bromley | Results |
| 23 May 2009 | | Rodmersham v Ashford Town Third XI | Bottles Lane, Rodmersham Green | Results |
| 23 May 2009 | | Sidcup v Rainham | Crescent Farm, Sidcup | Results |
| 23 May 2009 | | Walmer v Old Elthamians | Hull Park Sports Club, Deal | Results |
| 30 May 2009 | | Addington Village v Rodmersham | Park Road, Addington | Results |
| 30 May 2009 | | Ashford Town Third XI v Walmer | Stacians Park Annex Ground, Ashford | Results |
| 30 May 2009 | | Gravesend RF v Sidcup | Rectory Field, Gravesend | Results |
| 30 May 2009 | | Old Elthamians v Bromley Town | Foxbury Sports Ground, Chislehurst | Results |
| 30 May 2009 | | Rainham v Bexleyheath | Berengrave Park, Rainham | Results |
| 06 Jun 2009 | | Bexleyheath v Old Elthamians | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 06 Jun 2009 | | Bromley Town v Rodmersham | Hayes Lane Cricket Ground, Bromley | Results |
| 06 Jun 2009 | | Rainham v Gravesend RF | Berengrave Park, Rainham | Results |
| 06 Jun 2009 | | Sidcup v Ashford Town Third XI | Crescent Farm, Sidcup | Results |
| 06 Jun 2009 | | Walmer v Addington Village | Hull Park Sports Club, Deal | Results |
| 13 Jun 2009 | | Addington Village v Rainham | Park Road, Addington | Results |
| 13 Jun 2009 | | Ashford Town Third XI v Bromley Town | Stacians Park Annex Ground, Ashford | Results |
| 13 Jun 2009 | | Gravesend RF v Bexleyheath | Rectory Field, Gravesend | Results |
| 13 Jun 2009 | | Old Elthamians v Sidcup | Foxbury Sports Ground, Chislehurst | Results |
| 13 Jun 2009 | | Rodmersham v Walmer | Bottles Lane, Rodmersham Green | Results |
| 20 Jun 2009 | | Addington Village v Old Elthamians | Park Road, Addington | Results |
| 20 Jun 2009 | | Ashford Town Third XI v Gravesend RF | Stacians Park Annex Ground, Ashford | Results |
| 20 Jun 2009 | | Bromley Town v Sidcup | Hayes Lane Cricket Ground, Bromley | Results |
| 20 Jun 2009 | | Rodmersham v Rainham | Bottles Lane, Rodmersham Green | Results |
| 20 Jun 2009 | | Walmer v Bexleyheath | Hull Park Sports Club, Deal | Results |
| 27 Jun 2009 | | Bexleyheath v Ashford Town Third XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 27 Jun 2009 | | Bromley Town v Walmer | Hayes Lane Cricket Ground, Bromley | Results |
| 27 Jun 2009 | | Gravesend RF v Addington Village | Rectory Field, Gravesend | Results |
| 27 Jun 2009 | | Rainham v Old Elthamians | Berengrave Park, Rainham | Results |
| 27 Jun 2009 | | Sidcup v Rodmersham | Crescent Farm, Sidcup | Results |
| 04 Jul 2009 | | Addington Village v Bromley Town | Park Road, Addington | Results |
| 04 Jul 2009 | | Ashford Town Third XI v Rainham | Stacians Park Annex Ground, Ashford | Results |
| 04 Jul 2009 | | Old Elthamians v Gravesend RF | Foxbury Sports Ground, Chislehurst | Results |
| 04 Jul 2009 | | Rodmersham v Bexleyheath | Bottles Lane, Rodmersham Green | Results |
| 04 Jul 2009 | | Walmer v Sidcup | Hull Park Sports Club, Deal | Results |
| 11 Jul 2009 | | Addington Village v Ashford Town Third XI | Park Road, Addington | Results |
| 11 Jul 2009 | | Bexleyheath v Sidcup | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 11 Jul 2009 | | Gravesend RF v Walmer | Rectory Field, Gravesend | Results |
| 11 Jul 2009 | | Old Elthamians v Rodmersham | Foxbury Sports Ground, Chislehurst | Results |
| 11 Jul 2009 | | Rainham v Bromley Town | Berengrave Park, Rainham | Results |
| 18 Jul 2009 | | Ashford Town Third XI v Old Elthamians | Stacians Park Annex Ground, Ashford | Results |
| 18 Jul 2009 | | Bromley Town v Bexleyheath | Hayes Lane Cricket Ground, Bromley | Results |
| 18 Jul 2009 | | Rodmersham v Gravesend RF | Bottles Lane, Rodmersham Green | Results |
| 18 Jul 2009 | | Sidcup v Addington Village | Crescent Farm, Sidcup | Results |
| 18 Jul 2009 | | Walmer v Rainham | Hull Park Sports Club, Deal | Results |
| 25 Jul 2009 | | Addington Village v Bexleyheath | Park Road, Addington | Results |
| 25 Jul 2009 | | Ashford Town Third XI v Rodmersham | Stacians Park Annex Ground, Ashford | Results |
| 25 Jul 2009 | | Gravesend RF v Bromley Town | Rectory Field, Gravesend | Results |
| 25 Jul 2009 | | Old Elthamians v Walmer | Foxbury Sports Ground, Chislehurst | Results |
| 25 Jul 2009 | | Rainham v Sidcup | Berengrave Park, Rainham | Results |
| 01 Aug 2009 | | Bexleyheath v Rainham | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 01 Aug 2009 | | Bromley Town v Old Elthamians | Hayes Lane Cricket Ground, Bromley | Results |
| 01 Aug 2009 | | Rodmersham v Addington Village | Bottles Lane, Rodmersham Green | Results |
| 01 Aug 2009 | | Sidcup v Gravesend RF | Crescent Farm, Sidcup | Results |
| 01 Aug 2009 | | Walmer v Ashford Town Third XI | Hull Park Sports Club, Deal | Results |
| 08 Aug 2009 | | Addington Village v Walmer | Park Road, Addington | Results |
| 08 Aug 2009 | | Ashford Town Third XI v Sidcup | Stacians Park Annex Ground, Ashford | Results |
| 08 Aug 2009 | | Gravesend RF v Rainham | Rectory Field, Gravesend | Results |
| 08 Aug 2009 | | Old Elthamians v Bexleyheath | Foxbury Sports Ground, Chislehurst | Results |
| 08 Aug 2009 | | Rodmersham v Bromley Town | Bottles Lane, Rodmersham Green | Results |
| 15 Aug 2009 | | Bexleyheath v Gravesend RF | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 15 Aug 2009 | | Bromley Town v Ashford Town Third XI | Hayes Lane Cricket Ground, Bromley | Results |
| 15 Aug 2009 | | Rainham v Addington Village | Berengrave Park, Rainham | Results |
| 15 Aug 2009 | | Sidcup v Old Elthamians | Crescent Farm, Sidcup | Results |
| 15 Aug 2009 | | Walmer v Rodmersham | Hull Park Sports Club, Deal | Results |
| 22 Aug 2009 | | Bexleyheath v Walmer | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 22 Aug 2009 | | Gravesend RF v Ashford Town Third XI | Rectory Field, Gravesend | Results |
| 22 Aug 2009 | | Old Elthamians v Addington Village | Foxbury Sports Ground, Chislehurst | Results |
| 22 Aug 2009 | | Rainham v Rodmersham | Berengrave Park, Rainham | Results |
| 22 Aug 2009 | | Sidcup v Bromley Town | Crescent Farm, Sidcup | Results |
| 29 Aug 2009 | | Addington Village v Gravesend RF | Park Road, Addington | Results |
| 29 Aug 2009 | | Ashford Town Third XI v Bexleyheath | Stacians Park Annex Ground, Ashford | Results |
| 29 Aug 2009 | | Old Elthamians v Rainham | Foxbury Sports Ground, Chislehurst | Results |
| 29 Aug 2009 | | Rodmersham v Sidcup | Bottles Lane, Rodmersham Green | Results |
| 29 Aug 2009 | | Walmer v Bromley Town | Hull Park Sports Club, Deal | Results |
| 05 Sep 2009 | | Bexleyheath v Rodmersham | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 05 Sep 2009 | | Bromley Town v Addington Village | Hayes Lane Cricket Ground, Bromley | Results |
| 05 Sep 2009 | | Gravesend RF v Old Elthamians | Rectory Field, Gravesend | Results |
| 05 Sep 2009 | | Rainham v Ashford Town Third XI | Berengrave Park, Rainham | Results |
| 05 Sep 2009 | | Sidcup v Walmer | Crescent Farm, Sidcup | Results |
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