Career
Webb played for as a youngster, usually playing as a central midfielder, but left the club to focus on his school work. Whilst at Saint Aidan"s & Saint John Fisher Associated Sixth Form, Webb was called up to play for England Schoolboys. lieutenant was also during this time that he played in the Street Aidan"s Football team where from 2001–2008, the team dominated the North Yorkshire School Football circuit.
Webb was part of the team that reached the Semi Finals of the U18 English Schools Cup competition during 2007–2008.
The following year, his talent was recognised by the new Leeds manager, Gary McAllister. The highly academic Webb signed a one-year contract with the club on the basis that if he did not succeed as a professional football player in his first year, then he would move on to University to study Business Studies.
Jonathan joined Newcastle Blue Star on loan on 27 February 2009. He returned to Leeds after his loan spell at Newcastle Blue Star, signing a new 6-month contract which takes him to midway through the 2009-2010 season.
During the 2009-2010 season Webb had failed to make a single first team squad due to a hip injury and following two operations has had to retire from professional football.
On 13 January 2010 Webb"s contract expired and Leeds decided not to renew his deal making him a free agent.