Early career A product of the Tottenham Hotspur youth system, Henry signed a professional contract with the North London club at the age of 17. He was sent on loan to Southend United on 28 March 2003, on an agreement for the remainder of the 2002–03 season. He made his professional debut for Southend in a 2–0 victory over Darlington at Roots Hall on 5 April 2003, and started two more matches during the loan spell. Henry was released by Tottenham in November 2003, having not made any first-team appearances for the club. Following his departure from Tottenham, Henry had an unsuccessful trial at Luton Town, who were in administration during his time there. Having spent the rest of the 2003–04 season as a free agent, Henry was signed by Irish club Dublin City on a six-month contract in August 2004. He left Dublin City due to financial problems at the club. Stevenage Returning to England without a club, Henry signed for Conference National club Stevenage on an initial six-month contract in January 2005. He made his Stevenage debut in a 1–0 away victory at Gravesend & Northfleet in a Conference League Cup match on 25 January 2005. Four days later, on 29 January 2005, he made his league debut for the club in a 3–1 home win over Farnborough Town, playing the full 90 minutes. Henry played regularly under manager Graham Westley for the remainder of the 2004–05 season as Stevenage secured the final Conference National play-off place. He played in all three of the club's Conference National play-off matches, including the 1–0 Conference National play-off final defeat to Carlisle United. Henry remained at Stevenage for the 2005–06 season, making 35 appearances, as the club missed out on a play-off position. During the season, Henry was made captain by Westley in the club's 2–0 victory over Exeter City. Under the new management of Mark Stimson during the 2006–07 season, Henry played 49 times. Despite losing his captaincy in the early part of the season to Luke Oliver, Henry regained the position as club captain later that season. Henry had started the campaign in a central midfield role, reverting to the role of full-back following Stevenage's poor start to the season. Henry scored his first league goal for Stevenage on 3 April 2007, in a 2–1 home defeat against Kidderminster Harriers. Henry became the first player to lift a trophy