The Timbers nearly broke though in the very first minute, when a cross from Jorge Perlaza was just a bit to the wrong side of the attempted header from Kenny Cooper, so the weak shot was easily saved by Chivas USA goalkeeper (and former Timbers draft pick) Dan Kennedy. In the 10th minute, Perlaza had another good run down the left side, but he shot wide left as Kennedy charged off his line. Five minutes later, Perlaza stopped his own run when he thought he was offside, but no flag had gone up, and by the time he realized play was still going, Kennedy had charged out to block the shot, and Perlaza's shot went harmlessly wide right.

In the 20th minute, Cooper had another good header chance, this time on a feed from Steve Purdy, but the shot was right at Kennedy and easily saved. Eight minutes later, it was Perlaza threatening again, on an overlapping run and a nicely placed pass from Cooper, but his shot across the goal mouth eluded any charging Timbers players.

In the 33rd minute, Chivas USA had their first good scoring chance, when Marcos Mondaini slipped in behind the Timbers defense, but Timbers goalkeeper Jake Gleeson cut off and angle and made a nice save that took most of the pace off the shot, and Eric Brunner retreated to clear the ball. On the counter attack the Timbers were again attacking down the right side, with Ryan Pore making a nice pass across the goal mouth that once again eluded any Timbers forwards. Chivas got another good scoring chance shortly afterwards, as Francisco Mendoza had a nice run down the left side, but his shot was smothered well by Gleeson.

But just before the half, Chivas USA would go down a man as defender Andrew Boyens received his second yellow, presumably for persistent fouling as it was his fifth foul of the first half, and he was shown his second yellow for taking down Cooper, and the Timbers would have the man advantage for the rest of the match.

Scoreless at the half, Chivas USA packed their defense for much of the second half, often paying with eight players behind the ball, with the first good chance being a free kick from Portland's Cooper in the 62nd minute which was saved by Kennedy. Three minutes later, Victor Estupinan had a good look for the visitors, but was well wide left from 20 yards out.

In the 67th minute, the Timbers had another good opportunity when Cooper found Peter Lowry at the top of the box, but the Timbers midfielder attempted to one-time the shot when he probably had more time, and the shot was well over the bar. Nine minutes later, Chivas nearly took advantage of a bad Timbers clearance when Estupinan had another good look, but shot from just outside the top of the box was wide left and high.

In the 80th minute, a cross from Rodney Wallace found Perlaza just off the near post, but his attempted chest-trap was too hard trickled over the end line. Shortly afterwards, Kalif Alhassan had an open look near the top of the box, but his shot was over the bar.

In the 83rd minute, Chivas nearly took the lead when Justin Braun slipped in alone behind the Timbers backline, but Gleeson charged out of the box and made a slide tackle to stop the threat, and the Timbers were able to clear the rebound and it would lead to the first Timbers goal when Jack Jewsbury, who had only entered the match minutes earlier, was left unmarked as he moved down the center of the pitch, and took a shot from 35 yards out that bounced once on the wet grass, and slipped past Kennedy just inside the left post, and the Timbers had a 1-0 lead.

It only took three minutes to double the lead, when on a on the only corner kick of the match, taken by Jewsbury, Brunner had a nice headed shot blocked by a Chivas defender, but the rebound fell back to the foot of the Timbers defender, who powered in the rebound to double the margin to 2-0, and the lead would hold for the US Open Cup win, and the Timbers advance to the next round in San Jose which is to be played sometime next month.