Jordan Stewart

Leicester City

Stewart started his career at Leicester City, signing professional terms in the summer of 1999. He made his debut for the club against West Ham United on 22 January 2000. He made one more appearance for Leicester that season before being loaned to Division Two side Bristol Rovers, for whom he made four appearances. Semi-regular appearances from the bench followed in the 2001–02 season, before he established himself as a member of the first team in 2002–03, after the club's relegation to Division One. On 4 August 2002, Stewart scored Leicester's first goal at the new Walkers Stadium in a friendly match with Athletic Bilbao. Leicester's return to the Premiership in 2003–04 saw fewer games for Stewart, although he did score a memorable goal against Manchester City at the City of Manchester Stadium in Leicester's 3–0 win in November 2003. Relegation again saw Stewart hold down a starting position in 2004–05.

Watford

Stewart became Aidy Boothroyd's first signing for Watford, joining for £125,000 in July 2005. He started as Watford's first-choice left-back, but was dropped in October 2005 after a run of poor form. He retook the position from James Chambers in January, and started every game until he was dropped for the game against Wolverhampton Wanderers on 14 April 2006, after another run of poor form. However, he returned to the side as they went on to win the Championship play-offs, playing all three games. He was the only player in Watford's…

After serving as assistant coach for San Jose Earthquakes reserve side The Town FC for two seasons, Stewart was appointed as head coach of USL Championship side Monterey Bay FC in August 2024. He replaced former San Jose Earthquakes coach Frank Yallop. Simon Dawkins, a former teammate of Stewart's at San Jose, took on the assistant coach role for the remainder of 2024 and replaced Ramiro Corrales, another former teammate of Stewart. Stewart was dismissed as head coach of Monterey Bay on 29 April 2026.

Stewart and his close friend and fellow footballer Joleon Lescott launched a clothing label together in 2012 named LescottStewart.

Watford

Football League Championship play-offs: 2006