Early in the first half, it was the Islanders who were on the attack, and in only the 3rd minute, Corey Woolfolk made a open run into the box down the left side, forcing Portland goalkeeper Josh Saunders off his line, with the shot rebounding off Saunders' knee and barely over the bar. Two minutes later the Timber had a good chance of their own, with midfielder Tommy Poltl getting a good look briefly from the top of the box, but his shot was just wide right.

In the 11th minute, the visitors had another good opporunity when Edivaldo Sarafim-DaSilva got to a loose ball near the Timbers penalty spot just before the charging Timbers keeper, but his shot would be chipped just over the bar. For much of the rest of the first half, it would be the Timbers on the attack.

In the 19th minute, a Hugo Alcaraz-Cuellar free kick was headed towards the far post by Portland's Scot Thompson, and collected just outside the far post by Byron Alvarez, but his cross was deflected right to Islanders goalkeeper Dan Kennedy. Starting in the 23rd minute, the Timbers had a series of good chances on deep runs into the box, and dangerous crosses and corner kicks, but shots by Dan Antoniuk, Alvarez, and Thompson would be tipped wide by Kennedy or the Islanders defense.

In the 36th minute the Timbers had perhaps their best chance of the first half when Antoniuk jumped on a loose ball only about five yards out from the Islanders goal, but his point-blank shot was knocked wide by a kick save by Kennedy.

It appeared the teams would go into the locker rooms scoreless, but in the 45th minute, an Islanders corner kick bounced around in the box, and appeared to be collected by Saunders, but a collision in the box had Saunders on the ground seconds later, and the ball laying free just a few feet off the line. Woolfolk would jump on the ball first and blasted it into the roof of the net, and despite being outshot 6-2 and outplayed for much of the half, the Islanders held a 1-0 lead at the half.

The lead would not last long though. Only three minutes into the second half, an Alcaraz-Cuellar free kick from 30 yards out appeared headed into a mass of Islanders defenders near the penalty spot, but Antoniuk got his head to the ball first, with the Timbers striker placing a perfect shot just inside the right post to level the score at 1-1.

Five minutes later, the Islanders nearly re-took the lead when Rafael Ortiz-Huertas made a few nice moves to cut through two Timbers defenders down the right side, then crossed to what appeared to be an empty box, but the cross was near-perfect, hitting off the crossbar as it got over Saunders head, but no Islanders were in position to pounce on the rebound. Three minutes later, the Timbers had a dangerous cross of their own, with Poltl making a run down the right side, and his cross to an open Alvarez being barely tipped wide by a leaping Kennedy.

After controlling the possession for most of the second half, the Timbers finally found the go-ahead goal in the 71st minute, when Alcaraz-Cuellar and Antoniuk hooked up again, this time with Alcaraz-Cuellar serving up the corner kick which curved and dipped perfectly to the penalty spot, where a charging Antoniuk had to slide and scissor the shot to get a foot on it, but his shot bounced into the right side of the net, between Kennedy and an Islanders defender, and the Timbers had rallied for a 2-1 lead.

The Islanders had a good chance to draw level four minutes later when a high chip into the box was headed just wide left from eight yards out by Woolfolk.

In the 79th minute, after the Islanders had been committing multiple fouls in an attempt to slow down the Timbers, and expressing increasing dissatisfaction with the center referee, Alexis Rivera received a second yellow when he slammed the ball to the turf just behind the center referee, and in the following few minutes, with Rivera already ejected, Juninho DaSilva would also receive a red for leaving the bench area (having just been subbed out), and Rafael Ortiz also receving a yellow as the referees attemped to restore order. The Islanders would commit 29 fouls in all, 17 in the second half, and would total five yellow cards in addition to the two ejections.

The Islanders would never regain their composure after the fracas, and the lone good scoring chance in the last few minutes was a shot from the top of the box by Portland's Alvarez which forced a nice save by Kennedy, but the rally had drained any offense out of the Islanders, and the Timbers would hold on for the 2-1 victory.

Josh Saunders was not credited with any official saves in the win, while Dan Kennedy recorded six saves in the losing effort.