Career
College and Amateur
Stewart played college soccer at the University of Notre Dame, where he was named All-Big East his junior and senior seasons. He also played for Indiana Invaders in the USL Premier Development League. Professional
Stewart was drafted tenth overall pick in the 2005 Master of Library Science SuperDraft by Chicago Fire, but he saw limited action with the team in his rookie season.
He was traded to Real Salt Lake on July 25, 2006 in exchange for Ryan Johnson.
He was waived by Salt Lake at the end of the 2007 season. In 2008 Stewart signed with Moss FK of the Norwegian Adeccoligaen, but was released midseason without an appearance.
He later moved to Nybergsund Illinois. On February 13, 2009, he signed with the Carolina RailHawks of the USL First Division. After a year out of the game in 2010, Stewart returned to the field in 2011 when he signed with the National Security Council Minnesota Stars in the North American Soccer League.
He was loaned to Football Club Dallas of Major League Soccer on August 15, 2011 for the remainder of the 2011 Master of Library Science season.
Football Club Dallas declined a purchase option at the end of the loan. Stewart scored his first goal for Dallas in a CONCACAF Champions League group stage match, scoring the match-winning goal in a 1–0 victory over Toronto Football Club. On March 6, 2012, Minnesota traded Stewart to Fort Lauderdale Strikers in exchange for Martin Nuñez. International
Although born in the United States, Stewart has trained with the Canadian men"s national soccer team due to his ancestry.
He has yet to be capped by either nation, and had not formally pledged international commitment to either Canada or the United States.