 He began his career at Tottenham Hotspur, for whom he made twenty-one appearances in league and cup competitions.In the summer of 2000, IFK Hässleholm of the fourth-highest division in Sweden, sold Jon Jönsson to Tottenham for £70,000 and also agreed two loan deals for the Swedish club - that of Thelwell and Peter Crouch.He also won one England under-21 cap on 27 February 2001, as a substitute in the 4–0 defeat at home to Spain U21.