Stewart started his career at Leicester City, where he was relegated twice and once promoted to the Premier League. Whilst at Leicester he also spent a loan spell at Bristol Rovers. He joined Watford in 2005, and was part of a side that won promotion to Premier League, before being subsequently relegated.
Stewart's career began at Leicester City, where he experienced two relegations and one promotion to the Premier League. During his time with Leicester, he also had a loan spell with Bristol Rovers. He joined Watford in 2005 and was part of a team that achieved promotion to the Premier League before being relegated.