Stewart was drafted tenth overall pick in the 2005 MLS 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.[1] He was waived by Salt Lake at the end of the 2007 season.
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 FC.
Although born in the US, 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.