History of Puerto Rico Islanders FC

The team came into the season on a high, they had just played a preseason tournament against MLS teams and achieved very successful results. They also had signed several dangerous players like Panamanian trio Victor Herrera, a Panamanian international, Gustavo Avila, and Alberto Zapata, a new goalkeeper Josh Saunders, rookie Jay Needham^[7] The Force folded after one game in Houston.,^[2] plus a return of players like Marco Vélez, Petter Villegas and Noah Delgado. The squad was considered serious contenders for the title.

After one early success, the team took a turn for the worse. It was evident that Toribio Rojas had lost his edge and after an embarrassing 2:1 lost against bottom table Minnesota Thunder was let go from his coaching position and given the post of Youth System Director, when he left the team with a record of 1-3-3. Also attendance went down.

The FO quickly found a replacement in ex-FC Dallas coach Colin Clarke, who had found himself without a job after the debacle of the Virginia Beach Mariners. He immediately established himself as a hard and hotheaded coach. Because of the way he conducted the team's practice, he was given the nickname of "El General", because he worked the team like a general would with his troops.

The rapid change was also seen on the field, in the first game under Clark the team beat the Minnesota Thunder 2:1, just a week after it had lost against them. Clark and the Islanders turned around, even with some bad roster decisions by Clark in American Jared Montz and Jamaican Gregory Simmonds, he redeemed himself by signing players like Haitian Fabrice Noel, Englishman Taiwo Atieno and bringing Willie Sims on loan from the New England Revolution. These players had a positive impact on the squad and the team ended comfortably in 6th place, two spots on top of the last playoff spot.

The Islanders went into the playoffs with an air of confidence but facing powerhouse Montreal, passing the quarterfinals seemed very difficult. After a 2:3 loss in Montreal, the team came back at home with the 3:0 victory, winning the series 5:3. In the semifinals, the team faced the same problem but now against regular season champions Seattle Sounders. The Islanders lost at home but managed to tie the series in Seattle,^[8] losing the series 4–2 in penalties.

On June 16, 2008, Jonathan Steele was included in the USL's "All-Star Week Players" list.^[9] On June 27, 2008, the Islanders defeated the Minnesota Thunder with a score of 1–0. Two days later, they won the second game of the series 3–1.^[10] The Islanders began gaining more points in the second half of June and early July, earning a total of 24 points, positioning themselves in the second position of the league's global standing.^[11] On July 18, 2008, the Islanders defeated the Carolina RailHawks, reaching the second place of the league's standings.^[12] On July 27, 2008, the team closed a road trip with a 3–2 victory against Minnesota Thunder, securing their position.^[13] On August 8, 2008, the Islanders defeated Rochester Rhinos four goals to none. This victory placed the team in the top of the league's standing for the first time in the club's history.^[14] After tying with Rochester two days later, the team shared the position with the Vancouver Whitecaps.^[15] In the final stages of the tournament, the Islanders regained the first position and on September 19, they won the first Commissioner's Cup since their creation, clinching the first place in the league's regular season.^[16] The Puerto Rico Islanders became the first team of the USL league to win 4 individual honors from a total of 5; this includes Goalkeeper of the Year (Bill Gaudette), Most Valuable Player (Jonathan Steele), Defense of the Year (Cristian Arrieta) and Head Coach of the Year (Colin "General" Clarke). Islanders would go on to the USL 1 Division final in Vancouver and lose to the Whitecaps 2:1, in the team's first final.^[17]