The Timbers would be missing leading scorer Byron Alvarez, who received two yellows in the last Timbers Open Cup match vs. Seattle and would have to sit this one out, as well as regulars Gavin Wilkinson and Aaran Lines, both out with injuries. The Timbers also had to do without reserve forward Paul Conway, out with an injury, and defender Kevin Goldthwaite, just recently loaned to the Timbers from these very same Earthquakes, was pulled back before the game and played the second half for San Jose. The Timbers would start Jarrod Weis for the first time ever, taking Lines' spot at left-side midfielder, while Edwin Miranda and Garrett Marcum would attempt to shore up the defense.

The Timbers would get the better early chances, with Scot Thompson heading the ball just wide of the left post in the 2nd minute, and Fadi Afash getting an open look from near the top of the box in the 5th minute, but putting his shot right into the chest of San Jose goalkeeper Jon Conway.

The Earthquakes had their first good scoring opportunity in the 10th minute, when Ian Russell made a deep run into the Timbers box, but his attempt at a tight angle shot (or possible cross) was blocked wide by Portland goalkeeper Josh Saunders. The teams would then trade good shots that were just over the bar, the first by San Jose's Brian Mullan from the top of the box, then second by Portland's Hugo Alcaraz-Cuellar. Russell then made another good deep run for the Earthquakes in the 18th minute, but his low cross through the crease found no teammates and was easily cleared. Russell had another good look six minutes later as he was left open near the top of the box, but couldn't put the open shot on-net as he hit the shot about a yard high and wide.

The Timbers nearly took the lead in the 25th minute when an Alcaraz-Cuellar cross found Dan Antoniuk open near the penalty spot, but his header was just wide left. The Earthquakes would make the Timbers pay for their missed chance just two minutes later, when a seemingly innocent cross from Brad Davis bounced straight through to Wade Barrett as it appeared a Portland defender slipped on the NexTurf as he attempted to clear, and Barrett was wide open from eight yards out and scored easily to give the Quakes a 1-0 lead.

The Quakes had a good chance to widen the lead in the 35th minute when Alejandro Moreno was open inside the box to knock home a cross, but put the shot right at the Timbers goalkeeper who collected the shot easily. Four minutes later, the Timbers nearly gave the visitors a goal when they gave away the ball near their own goal, but Dwayne DeRosario's open shot from just inside the box was stopped by a diving Saunders and cleared by Miranda. Just before the half San Jose would have another good chance, with Davis getting an open look from near the top of the box, but his low shot was smothered by a scrambling Saunders, and the half would end with the Earthquakes holding a 1-0 lead.

In the 52nd minute, a second San Jose goal seemed certain when DeRosario had a shot at an open net after a low cross found him wide open, but the San Jose midfielder put the shot past the right post. DeRosario nearly got an assist just three minutes later when his pass found the head of Mullan inside the box, but Mullan's shot was just over the bar.

For the next stretch of the match it was the Timbers who controlled much of the run of play, with Antoniuk narrowly missing in the 57th minute when he avoided two defenders with a good run into the box, but hit his shot inches past the left post from 15 yards out. Two minutes later, Portland's Tom Poltl also came very close to tying the score when he hit a dipping shot from 30 yards out that appeared headed for just under the San Jose crossbar, but a fine tip save from Conway kept the ball out of the net, and kept the Earthquakes in the lead.

Once again, the Earthquakes responded to a good Timbers chance by putting the ball into the Timbers net. In the 65th minute, Russell played a ball ahead from midfield to an open Mullan, who was running slightly wide and pulled Saunders out of his net, and put the ball into the Timbers net past the charging goalkeeper, and the Earthquakes had widened the lead to 2-0.

In the 76th minute, the Timbers had a good chance to pull one back but a low cross by Thompson bounced harmlessly across the face of the San Jose goal. In the 82nd minute, San Jose appeared ready to equal their 2004 score of 3-0 over the Timbers when DeRosario had a chance to chip a charging Saunders into the open net, but put the shot wide to the left.

The Timbers would have their best chance of the entire night in the 83rd minute when a header by Alcaraz-Cuellar off a cross would bounce off the turf and up off the crossbar, but the Earthquakes were eventually able to clear the ball and end the threat.

San Jose's DeRosario would have one more look at a nearly open net, this time in the 87th minute, but once again could not put the ball between the posts, but in the end it did not matter as the Earthquakes would earn the 2-0 victory and a trip to the US Open Cup 5th round.

Portland's Josh Saunders had seven saves in the losing effort, while Jon Conway recorded four saves for the Earthquakes.