Smith began his professional career playing for the Dandy Town Hornets, who he helped win the 2003–04 Cingular Wireless Premier Division title in his first year at the club. In his second season, he led the league in scoring as Dandy Town finished two points behind Devonshire Cougars. He captured his second trophy with the club in 2005 leading the Hornets to the Bermuda Champions Cup. After two successful seasons in Bermuda he moved Major League Soccer and signed with New England Revolution in April 2005. He made his first start, and scored his first goal, on 4 June 2005 during a 1–1 tie with the Kansas City Wizards. Smith also scored the winning goal against the MetroStars which led the Revolution to the MLS Conference Championship in 2005. He came to be known in New England for his inconsistent play, showing occasional flashes of brilliance, but also making fundamental mistakes. He was also known for his pace and his crucial crosses which pick out his teammates for easy finishes. He moved from an out and out striker to an attacking left wing back. In 2007 and 2008 he was the regular starter on the left wing and scored several crucial goals. On 26 November 2008, Smith was selected by Seattle Sounders FC with the fourth pick in the 2008 MLS Expansion Draft. Before ever playing a match for the Sounders, he was traded to New York Red Bulls in exchange for allocation money. On 30 July 2009 New York waived Smith. After trialing with Southend United, and playing for their reserves in a 4–0 defeat to Norwich City reserves in September 2009, Smith was offered a professional contract at Lincoln City, having impressed new manager Chris Sutton on a 10-day trial. On 23 October Smith was reported to have signed a 'short-term' deal with Lincoln. Smith became an instant first team regular at Lincoln. However, he was dropped after six games due to consistently poor performances, his final one coming in an FA Cup game at Northwich Victoria and he struggled badly against a side who were two divisions below the Imps. He was released when his contract expired on 7 January 2010. He was voted in an online poll as the worst of the 41 players to have represented Lincoln City during the 2009/10 season. Smith re-signed with New England Revolution on 26 March 2010 after trialing with the team during pre-season. After the 2010 Major League Soccer season New England declined Smith's contract option and he elected to participate in the 2010 MLS Re-Entry Draft. Smith became a free agent in Major League Soccer when he was not selected in the Re-Entry draft. On 7 March 2011 he signed with Carolina RailHawks of the North American Soccer League. However, Smith was not listed on the 2011 roster released by the club on 4 April 2011. In an interview with Bermuda's The Royal Gazette on 7 April, Smith stated he would not play for Carolina due to a contract dispute.
