The top three teams in the tournament – W Connection, Puerto Rico Islanders, and San Juan Jabloteh – qualified for the 2009–10 CONCACAF Champions League.

The draw for the first round was held at the CONCACAF office in New York City on January 15.

The schedule for the first round legs was updated on March 11 due to necessary travel accommodations for clubs and local events occurring in Aruba and Haiti that would conflict with the original match schedule.

[8] In Jabloteh's return leg to Suriname they were without head coach Terry Fenwick, who did not travel with the team because he had not been paid by the club since the end of the 2008 TT Pro League season.

All of the matches in the final round will be played at Marvin Lee Stadium in Macoya, Trinidad and Tobago.

The Puerto Rico Islanders were seeded and received a bye directly into the final round.