After failing to settle at any football league academy, Smalling opted to continue his education at Chatham Grammar School for Boys. Whilst still at school he played for Isthmian League side Maidstone United. At the age of 17, Smalling made his competitive debut for 'The Stones', starting against Canvey Island in the Isthmian League Cup.
In June 2008 Smalling signed for Premier League side Fulham. He was made captain of the club's Development Squad by manager Billy McKinlay.
Manchester United announced that they had signed Smalling, with the player staying at Fulham for the remainder of the 2009–10 season before joining United for 2010–11.
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