Thirty-one national associations affiliated with the CFU were invited to participate, with each eligible to send two clubs, usually their league champions and runners-up. However, many member nations did not send a representative team every year. CFU also allowed
Antigua Barracuda,
Puerto Rico Islanders, and
Puerto Rico FC (all now defunct) to compete despite being members of the
United States league system. This tournament currently sent three or four teams to
CONCACAF competitions: the champions enter the
CONCACAF Champions League, the runners-up and third place teams enter the
CONCACAF League, and the fourth place team competed in a playoff with the
CFU Club Shield winner for a spot in the CONCACAF League. The CFU presented an exact replica of the championship trophy to the winning team for their permanent possession.
Participation of member associations The following associations have never had any team participate in a Club Championship: •
Anguilla •
British Virgin Islands •
Grenada •
Turks and Caicos Islands Associations in italics have had teams participate in the Caribbean Club Shield == Past winners ==