In preliminary action for the chance to participate in the Group Stage of the 2009/2010 tournament, the Islanders were initially paired up against an established MLS side, Toronto FC. The Islanders took the first leg from the Canadian club 1-0 through a 67th minute goal from Kendall Jagdeosingh. A long Islanders’ free kick was sent into the back corner of the keepers’ area and was headed dangerously across the box. Jagdeosingh was able to wrestle the ball away from Toronto goalie Stefan Frei before firing high into the net from an acute angle to stun the home fans.
The job was not yet finished for the Islanders until the second leg was played out to a 0-0 draw in Bayamón. The Islanders moved passed the MLS side and into CONCACAF Champions League Group Stage action.
Islanders' Head Coach Adrian Whitbread was proud to recount the night for prislandersfc.com:
“It was a great night for us. We got the win away and hung on for the second leg. He (Jagdeosingh) is a guy who could put it in the back of the net or hit it 50 yards over the bar. The joy of the guys going into the locker room was really quite memorable”.