I realize the competition is only two years old, but here's the best finish by country.
Belize - Prelims: Hankook Verdes (2008/09)
Canada - Quarterfinals: Montreal Impact (2008/09)
Costa Rica - Group Stage: Saprissa (2008/09 and 2009/10)
El Salvador - Group Stage: L.A. Firpo (2008/09), Isidro Metapan (2009/10)
Guatemala - Quarterfinals: Comunicaciones (2009/10)
Honduras - Quarterfinals: Marathon (2008/09 and 2009/10)
Jamaica - Prelims: Harbour View (2008/09)
Mexico - Champions: Cruz Azul (2008/09), Pachuca (2009/10)
Nicaragua - Prelims: Real Esteli (2008/09)
Panama - Quarterfinals: Arabe Unido (2009/10)
Puerto Rico - Semifinals: Puerto Rico Islanders (2008/09)
Trinidad & Tobago - Group Stage: Three Teams
USA - Quarterfinals: Houston Dynamo (2008/09), Columbus Crew (2009/10)
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