From TheChels.info - The Chelsea Football Club Wiki
James Simmonds (born 3 December 1987 in Hammersmith, London, England) is a midfielder who formerly played for Chelsea's Academy team and is now a member of the academy coaching staff.
James joined Chelsea as a highly-rated schoolboy, coming from the same Isleworth school as Michael Mancienne.
Initially breaking into the Under-18 team as a 15 year-old, James was well regarded as a talented winger and accelerated through youth team football into the reserve setup at a very young age. Unfortunately, he never quite kicked on and, after a loan spell at Cardiff City came to nothing, he was released on a free transfer.
James, who could also have represented England, chose to play for the Republic of Ireland at Under-19 level.
Youth Team Football
Reserve Team Football
Post Chelsea Career
A spell at Dover Athletic ended when he joined up with the Glenn Hoddle Academy in Jerez. A move from ther followed to Ecija in the lower Spanish tiers, before he returned to England and Dover on loan in March of 2010. He joined Hampton & Richmond Borough for the 2011-12 season and left for Hemel Hempsted Town in 2014 whilst continuing his coaching career in the Chelsea academy. As of the start of the 2018-19 season he was the club's Under-16 Head Coach.