The Timbers fans had barely found their seats when the Timbers broke through in just the 2nd minute on a free kick from Andrew Gregor. From about 35 yards out to the goalkeeper's left, Gregor played a curling pass into the goalmouth that missed everybody, bounced once and slipped inside the left post past former Timbers goalkeeper Josh Saunders, and with their first shot of the season, one minute and 25 seconds into their first match, the Timbers had taken a 1-0 lead.

Five minutes later, the Timbers had another good chance with a free kick just outside the Islanders box that Gregor curved towards the left post, but Saunders was able to knock down then collect the free ball. Three minutes afterwards, it was Troy Ready attacking down the left side, and he cut back and hit a hard shot that Saunders tipped just over the crossbar. In the eleventh minute, a near-replay as Gregor's high shot from 25 yards away on a free kick was once again pushed over the bar by Saunders.

In the 18th minute, the Timbers appeared ready to take a 2-0 lead when Gregor was pulled down from behind and the referee pointed to the spot, and defender Mauricio Segovia took his frustration out on the corner flag. But the Timbers failed to convert when Gregor approached the shot very, very slowly, then placed the penalty right at Saunders, who did not move and made an easy save, and the score remained at 1-0 to the Timbers.

The Timbers surprised the Islanders with their physical play: challenging every free ball, running to meet passes, and knocking them off the ball, which the visitors did not appear ready for. The match would get more scrappy is it went on, with a total of nine yellow cards to be issued before the night was out.

The Islanders finally had their first shot on goal in the 23rd minute when a free kick from 25 yards out was directly into the hands of Timbers goalkeeper Josh Wicks. Then in the 28th minute, the Timbers were within inches of taking the lead when a nice pass from Luc Harrington had Ready on a dead run into the box, and he rounded Saunders and appeared to have an open net, but hit the left post from just a few yards out, and a shot by Chris Bagley off the rebound was cleared acrobatically off the Islanders line by Segovia to keep the match 1-0.

In the 37th minute, the Islanders would show their first good pressure of the match after a Wicks giveaway, but the visitors were unable to capitalize as three shots were blocked off their feet by the Timbers defense, then a deep cross was snared by Wicks to end the threat.

The Timbers would have one more good chance, just before the end of the half, when Ready made a deep run down the left side, and his dangerous cross was deflected by a diving Saunders, and the half would end with the Timbers holding a 10-2 advantage in shots, and a 1-0 lead on the scoreboard.

Just two minutes into the second half, the Timbers would find the ball placed at the 12 yard spot again as a Timbers player was pushed down in the box on a Timbers corner kick. Gregor would once again take the penalty kick, but was once again denied as the midfielder's hard shot hit the upper left corner of the goal and bounced back out, and despite two chances to widen their lead from the spot, the Timbers still only had a 1-0 lead.

The stay of execution for the Islanders lifted the visitors and seconds later, Victor Manuel Herrera had a great run deep into the Timbers box, with his first shot being stopped by Wicks, and his rebound shot kissing the crossbar as it went over the top.

But before the Islanders had a chance to build on their momentum, a steal by Ready near midfield led to another nice through ball from Harrington to Scot Thompson, whose cross from the right side bounced through to Ready, who hit a right-footed shot that hit the right post this time, and the rebound deflected up slightly off Saunders, and Luke Kreamalmeyer was on the spot and dove head first into the ball and knocked it home to give the Timbers a 2-0 lead.

In the 63rd minute, the Islanders put together a great series of passes, and a flick-on by former Timber Edwin Miranda to Alen Marcina had the Puerto Rico striker in on Wicks alone, but the Timbers goalkeeper charged off his line and got to the ball just as Marcina took the shot to make the save.

Over the next 20 minutes, both teams showed good possession at times, but no good shots on goal until the 83rd minute, when the Islanders moved the ball down the middle with a number of quick passes, and a header from Marcina to Alberto Zapata, who appeared a stop offside, but the flag stayed down and Zapata chipped a frozen Wicks, and just like that, the Islanders had pulled back to 2-1.

But it only took about a minute for the Timbers to push the lead back out to two goals when a Timbers free kick from just outside the Islanders box was curled perfectly into the upper left corner by Gregor for his second free kick goal of the match, and the Timbers had widened the lead to 3-1, which would be the final score as neither team seriously threatened again.

Josh Wicks was not credited with any saves in the win, while Josh Saunders had four saves in the losing effort.