The Canadians took the place of the old Caledon Flyers. The Flyers played in Caledon from 1976 until 1990 in the Mid-Ontario Junior C Hockey League. In 1990, the team folded but after two seasons the Central Junior B Hockey League granted the town a new team.
The Canadians spent one season in the Central Junior "B" Hockey League before joining the Metro and one season after with the Ontario Provincial Junior A Hockey League. The Canadians were owned by a creator of Trivial Pursuit, but folded the very successful team after a long feud with the Caledon City Council who controlled the local arena.