Spurs' young midfielder Ross Fitzsimon played for Norwich City Reserves in their 2-1 victory over Portsmouth on 6th May 1999. Impressing in that game, Ross signed for Norwich on a Bosman free transfer on 1st July 1999. He was expected to play primarily in the Reserves and Academy side with the future aim of breaking into the first team.

Ross never established himself in the Norwich Reserves and in mid February 2000, it was announced that he would be departing Norwich on a free transfer. The club began circulating his name to other Nationwide and Conference clubs in February so that he had an advantage over those players freed at the end of the season.

In March 2000, Ross had a trial with Plymouth Argyle, joining Barrington Belgrave and Jon Sheffield on the English Riveria. In August 2000, Ross played for a Notts Forest side in a pre-season friendly at Aldershot that resulted in a 2-2 draw with Ross scoring one of the goals. Ross later had a trial with Watford playing for their reserves in a defeat at Leicester. He has also had a run out with Stevenage's second string. He is currently playing for Harrow Borough in the Ryman League