In 2006 the Islanders venture into the international stage participating in the CFU Club Championship, in hope of qualifying for the CONCACAF Champions Cup. This is possible because Puerto Rican football is governed by the Federación Puertorriqueña de Fútbol instead of the United States Soccer Federation. This first attempt at international success was the first time a team from Puerto Rico ever participated in its confederation's club competitions. The CFU Club Championship 2006 played in November saw the Islanders host Group C which included Hoppers F.C. (Antigua and Barbuda), W Connection (Trinidad and Tobago) and Fruta Conquerors (Guyana), the latter dropped out of the tournament weeks before group play. The Islanders beat Hoppers FC 3–1 but lost to W-Connection 0–1 ending the squads first international appearance.
In October 2007, the Islanders came into the CFU Club Championship 2007 with a much stronger squad, which was relatively unchanged from the squad that made it to the semifinals of the USL First Division playoffs and it showed, making it all the way to the tournaments semifinals losing out to Joe Public F.C. 0:1 from a late goal. The entire tournament was played in Trinidad and Tobago, the Islanders headed their group with a 2:2 tied against Harbor View FC, which later became the tournament's champions, and two victories. In this tournament, the team also broke several of their on-field records, it achieved its highest score line, a 10:0 victory over Hitachi Centre SAP FC, in the same game Fabrice Noël scored the team's first ever hat trick with a tally of four goals. This would be the last time the Islanders would play to try to qualify to this incarnation of the confederations top club tournament, since this competition format was abandoned in 2008.
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