In May 2002, Wheeldon joined the Calgary Storm of the A-League to play under the management of his father, Tommy Wheeldon Sr.[2] He went on to make 28 appearances for the club across two seasons.[3] During his time as a player, he also worked as a full-time academy coach and soccer camp director for the club.[4]
Coaching career
Calgary Foothills
After the Calgary Storm folded, Wheeldon decided to remain in Canada and help develop grassroots football. After four years as a director for a local soccer academy, he joined the Calgary Foothills as assistant technical director in 2007 and was promoted to technical director a year later. In 2015, Wheeldon was named as head coach as the club joined the Premier Development League. In his second season as head coach, Wheeldon guided the team to an appearance in the PDL Championship Final before losing to the Michigan Bucks.[5] In 2016, Wheeldon received the Jack Buckler Award for outstanding contribution to the sport of soccer within Calgary and area.[6]
After having accepted the role as head coach and general manager of Cavalry FC, Wheeldon led Calgary Foothills to the 2018 PDL Championship, defeating Reading United AC 4-2.[7]
During the 2023 CPL campaign, Wheeldon led Cavalry to the victory of the regular season, and won his second Coach of the Year Award as a result.[15][16]