After spending many of his youth years with English academies Exeter City and Plymouth Argyle, Wheeldon signed his first professional contract with Torquay United in League Two.
[1] Wheeldon would go on to spend some time in Belgium with Montegnée before returning home to play for non-league club Hungerford Town.
[4] On 26 January 2021, Cavalry announced that Wheeldon had left the club in order to pursue a career in coaching.
[1] In 2013, Wheeldon became manager of the Calgary Foothills Skills Academy, a role he retained after returning to professional football in 2019.
Wheeldon went on to win the first League1 Alberta season in 2023, before being named assistant coach and technical director with Cavalry FC.