| Rottingdean Village | | 2007 | | Preliminary Round | 02-09-2007 | | Eastbourne Town | Rottingdean Village | 0-6 | | First Qualifying Round | 16-09-2007 | | Canterbury City | Rottingdean Village | 4-1 | |
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| 2008 | | Preliminary Round | 07-09-2008 | | Rottingdean Village | Eastbourne Town | 0-1 | | 2009 | | First Qualifying Round | 27-09-2009 | | Rottingdean Village | Canterbury City | 0-2 | | 2010 | | First Qualifying Round | 03-10-2010 | | Seahaven Harriers | Rottingdean Village | 5-2 | | 2011 | | First Qualifying Round | 02-10-2011 | | London Corinthians | Rottingdean Village | 3-2 | |
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| 2012 | | First Qualifying Round | 30-09-2012 | | Rottingdean Village | New Forest | 3-1 | | Second Qualifying Round | 14-10-2012 | | Maidstone Town | Rottingdean Village | 9-1 | | 2013 | | First Qualifying Round | 22-09-2013 | | Rusthall | Rottingdean Village | 4-1 | | 2014 | | First Qualifying Round | 28-09-2014 | | AFC Wimbledon Development | Rottingdean Village | 3-0 | | 2015 | | First Qualifying Round | 06-09-2015 | | Rottingdean Village | Crawley Wasps | 1-8 | | 2016 | | Second Qualifying Round | 18-09-2016 | | Worthing Town | Rottingdean Village | W/O | |
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