Stewart attended South High School Torrance, CA, where he was a standout player voted to All-League and All-CIF awards.

Stewart played college soccer at the University of Notre Dame, where he was named All-Big East his junior and senior seasons.

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.

[2] After a year out of the game in 2010, Stewart returned to the field in 2011 when he signed with the NSC Minnesota Stars in the North American Soccer League.

On March 6, 2012, Minnesota traded Stewart to Fort Lauderdale Strikers in exchange for Martin Nuñez.