Jamie Windows played as a triallist for Norwich's Under 19 clash with Tottenham on April 7th 2001, scoring what would be the match winner in a 2-1 victory. Jamie previously played for Southend's youths. He has also had trials with Hull City and Stevenage. He joined Chelmsford City but was loaned out to Maldon Town to gain first team experience.

Jamie then played for Ryman League side Heybridge Swifts. In April 2003, he accompanied three other former Canaries (Robert George, Danny Self and John Sutton) on a trial for Cambridge United. In all there were seven triallists in United's reserve team clash with Reading on 9th April 2003 which they lost 3-2 with Jamie Cureton scoring Reading's winner. The other triallists were Shaun Humphries (Stoke), Liam Kearney (Notts Forest) and Chris Wild (Orient).

In June 2004, Jamie joined Maldon. He later played for Benfleet.