Jay Wheeldon played for Exeter City under-17s in 2003/04. He also played youth football for Plymouth Argyle before going on to play for Torquay United ahead of a long playing and coaching career in Canada.

Jay, son of ex-Exeter City coach and Football in the Community lead Tommy Wheeldon senior (born 1957) who played in the Football League for Torquay United in 1981/82 and 1985/66, appeared for Exeter City under-17s in 2003/04 having been a member of the age-group set-up several years. He also played youth football for Plymouth Argyle.

He was at Torquay United in 2006/07 and was an unused substitute in the club's final game before relegation from the Football Leagye. Moving to Belgium in 2008, he signed for Royal Racing Football Club Montegnée where he played over 80 games scoring 10 goals. Back in England Jay played for Hungerford Town between 2011 and 2013.

He moved to Canada in play for Calgary Foothills in 2014 and later played for Cavalry FC, another Calgary club. In Canada, Jay joined his father Tommy senior and his brother Tommy junior, who were both involved in various capacities at the two Calgary clubs (along with Leon Hapgood, ex-Torquay United and Taunton Town).   

Jay retired from playing in at the start of 2021 to move into coaching on a full-time basis having already coached extensively on a part-time basis. As of 2023 he was head coach and academy director at Calgary Foothills and under-20s coach at Cavalry.