Career
After graduating from the Lynx Academy he signed for the Oakville Blue Devils of the Canadian Professional Soccer League, playing under former Director of Lynx Academy Duncan Wilde. He made his debut on September 11, 2005 against Saint Catharines Wolves, and scored his first goal on September 15, 2005 against North York Astros. In 2006 he returned to the Lynx, where he was re-united with former Blue Devils coach Duncan Wilde.
He made his debut on April 22, 2006 against the Virginia Beach Mariners.
On July 16, 2006 against the Atlanta Silverbacks he broke his leg in a collision with a Silverback player, forcing him to miss the rest of the season. Brampton Lions
After recovering from his injury Shepherd signed with the Brampton Lions for the 2008 Computer Science Laboratory season.
Shepherd ended his two year goal drought on September 20 against North York Astros, where he scored two goals in 3-1 victory. He continued his fine form in a cruising 6-0 victory over London City where he recorded two goals and clinched a playoff spot for the Lions.
On May 14, 2009 the Brampton Lions re-signed Shepherd for the 2009 season.