Career
A trainee with Tottenham Hotspur from August 1994, Simon went on loan to Leyton Orient in October 1999. He was sent off in the 2002 FAI Cup Final as were beaten 2-1 by Dundalk. At the end of the 2004 season, Webb moved along with Damian Lynch to
He has become a regular fixture in the side, captaining the side on occasions and has added to his collection of medals by winning the FAI Cup in 2005 and the Setanta Cup in 2006 and 2007.
He retired in January 2008. Webb played for the Republic of Ireland national under-19 football team in the 1996 Union of European Football Associations European Under-18 Football Championship finals in Luxembourg.