Lewisham lad Wesley O'Connor attracted the attention of London's clubs as a youngster whilst playing for Greenwich Borough, Selsdon and South London schools. He instead opted for the Canaries instead of Crystal Palace, Milwall or Charlton. His choice being described in the 5th November 1994 matchday programme as "I liked the Norwich youth setup better. I thought there was more chance of doing well here". The fact that family friend Lee Power was at Carrow Road helped. Wesley progressed through the Under-14, Under-15 and Under-16 sides into the youth side but his career did not reach the first team

Wesley played for Dr Martens Southern League Premier Division side Crawley Town and came on as substitute against King's Lynn during the 1997/98 season. He also spent some time with Scottish side Dunfermline and was interested in signing for Tony Spearing's King's Lynn. Wesley played for Lynn during the 1998/99 pre-season friendlies but did not impress Spearing.

The February issue of Team Talk magazine revealed that Wesley had been released by Leatherhead of the Ryman League. The April edition showed that Wesley had signed up with Fisher Athletic.