The Islanders clinched the USL-1 regular season title at home on September 19th with a 1-1 draw against the Atlanta Silverbacks, at the Juan Ramón Loubriel stadium in Bayamón, with one game to go in the season. The Islanders finished the regular season on the road with a scoreless draw in their last game against the Montreal Impact, ending the 30-game season in first place with the most points, 54. The Vancouver Whitecaps followed the Islanders in 2nd place with 53 points, and the Impact finished 3rd with 42 points.

Islanders’ Director Stuart Klapper received on behalf of the team the 2008 Progress Award, which is the honor to the team that has made the most progress this season, across all the United Soccer Leagues (not just the USL-1).

Previously the Islanders also swept the annual USL Players Awards with the Goalkeeper of the Year award for Bill Gaudette, Cristian Arrieta as Defender of the Year, and Jonathan Steele as Most Valuable Player. Additionally, Colin “General” Clarke, won the Coach of the Year award.