Stewart appeared in a career-high 17 games year and was a solid contributor in the midfield. His first action with the Bulldogs came in 2004. All three of his points that year came in Ivy League play. He scored in Yale's 4-2 win over Princeton, his first career goal, and had an assist in a win at Cornell. At Choate Rosemary Hall, he lettered in soccer for three years and captained the squad as a senior. During the 1999 season, Choate was WNEPSA and New England champions. In 2002, Stewart was both a New England and WNEPSA all-star. He also competed on the Oakwood Soccer Club, which earned a state title in 1999.