Career
Born in Ashford, Kent, Wynter joined Gillingham"s youth system at under-15 level, and signed as a professional at the beginning of the 2008-2009 season. After loan spells at Ramsgate and Dover Athletic, he made his league debut for Gillingham on 26 December 2009 in the home 1–0 defeat to Brentford. Wynter rejoined former club Dover Athletic on a two-year deal in August 2010 after Gillingham decided not to renew his contract.