| Maidstone Town | | 2008 | | First Qualifying Round | 28-09-2008 | | Maidstone Town | Canterbury City | 2-1 | | Second Qualifying Round | 12-10-2008 | | Ebbsfleet United | Maidstone Town | 1-0 | | 2009 | | First Qualifying Round | 27-09-2009 | | Ramsgate | Maidstone Town | 0-9 | | Second Qualifying Round | 11-10-2009 | | Tower Hamlets | Maidstone Town | 1-3 | | Third Qualifying Round | 25-10-2009 | | Haywards Heath Town | Maidstone Town | 1-2 | | First Round | 08-11-2009 | | Enfield Town | Maidstone Town | 3-1 | | 2010 | | Second Qualifying Round | 24-10-2010 | | Milton & Fulston | Maidstone Town | 1-5 | | Third Qualifying Round | 14-11-2010 | | Maidstone Town | Eastbourne Town | 3-1 | | First Round | 02-01-2011 | | Ebbsfleet United | Maidstone Town | 3-0 | | 2011 | | First Qualifying Round | 02-10-2011 | | Victoire | Maidstone Town | 1-7 | | Second Qualifying Round | 23-10-2011 | | Chichester City | Maidstone Town | 4-1 | | 2012 | | First Qualifying Round | 30-09-2012 | | Victoire | Maidstone Town | O-W | | Second Qualifying Round | 14-10-2012 | | Maidstone Town | Rottingdean Village | 9-1 | | Third Qualifying Round | 11-11-2012 | | Maidstone Town | University Of Portsmouth | 1-3 | |
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