From the opening whistle, it would be the Timbers would control much of the run of play, with several players using the rare start to show their talent. The first good Timbers chance would be in the third minute, when Chris Bagley’s dipping shot from 20 yards out was just over the bar. The Timbers continued to control most of the possession, and in the 11th minute, Leonard Griffin’s blast from 10 yards out was just over the bar. The Timbers had another good chance 4 minutes later when Justin Thompson’s header was inches over the bar from close-in off a Bagley cross.

Hollywood United’s first scoring chance would come in the 20th minute, as former Timber Matt Taylor attacked Timbers rookie Scott Bolkan and beat the Timbers defender down the left side for an open run, and crossed to a wide-open Derk Droze with a sitter in front of the Timbers goal, but Droze badly mis-hit the shot and it trickled wide right.

Two minutes later the Timbers would have another great chance when Chris Brown was able to turn on the ball about 10 yards out from the Hollywood United goal, but his shot was stopped by a nice kick save from goalkeeper Javier Barragan.

In the 24th minute, Barragan would make another nice save as Portland’s Kiki Lara hit a curling free kick from 30 yards out that was curling to the upper right corner, but Barragan’s diving save kept the match scoreless.

But eight minutes later, from about the same spot, a free kick from Brown would leave Barragan with no chance, as the Portland striker’s low shot deflected off the Hollywood United wall, and into the left side of the net, and the Timbers had scored at home for the first time since April 26, and the Timbers had a 1-0 lead.

In the 38th minute, Hollywood United would come within inches of tying when after another attack down the Timbers left side, a corner kick by another former Timber, Alex Bengard, was cleared right back to Bengard, whose cross was headed by Droze and hit off the right post before being cleared.

A minute later, Portland’s Bryan Little had a nice turn at the top of the Hollywood United box, but his shot was wide left. A minute later, the Timbers had another good chance when Oka’s low shot on the wet turf had to be smothered by Barragan.

Having outshot their guests 10-2 as the match neared halftime, the Timbers were probably feeling good about their first half peformance, but Taylor would change the momentum as he would go 1-on-3 into the Timbers box and went down on contact from Tim Karalexis, and the center referee pointed to the spot, and Taylor would step up and put home the penalty kick, and would take the boost of confidence into halftime, level with the Timbers at 1-1.

After the Timbers had a few chances in the Hollywood United box early in the second half, the badly outshot visitors suddenly found their form and signaled that they weren’t going to go down easy when in the 49th minute, Brian Dunseth’s blast from 20 yards out was off the right post, and though it was knocked in on the rebound by Bengard, he was well offside when the first shot was struck, and the goal was waved off.

After the narrow escape a few minutes earlier, the Timbers responded with a beautiful goal in the 52nd minute as Neil Dombrowski pushed the ball down the left side, then a soft cross was run onto by Oka, whose powerful header was just inside the left post to give the Timbers a 2-1 lead.

Just barely a minute later, the Timbers looked ready to take command of the match when Little was tackled just inside the 18-yard box by LJ Reinhart, and the referee pointed to the spot. Takayuki Suzuki would step up to take the penalty for the Timbers, but his shot was saved by Barragan, and Oka missed a good chance on the rebound, and Hollywood United dodged the bullet to remain within a goal of the Timbers.

The 58th minute would be full of drama as it started out with Barragan coming a good 15 yards out of his box to clear a long ball back into the Timbers end of the field, and after second half substitute Jason Boyce's blast forced a reaction save from Portland goalkeeper Jordan James, a rebound header was headed out by Griffin, but as the ball deflected wide to Bengard, he was taken down near the edge of the box by Lara, and once again the center referee would point to the spot. Taylor once again stepped up and finished the penalty, and just a few minutes after thinking they were probably out of the match when the penalty was awarded at the far end, Hollywood United had drawn level again at 2-2.

For the next twenty minutes, it was the visitors who would control much of the run of play as they had been thrown a lifeline and smelled an upset. Still mostly attacking the inexperienced left side of the Timbers defense, Hollywood United did have a few good looks, but managed only a few weak shots right at James that were easily saved. Both teams were tightening up in the midfield, knowing that the next goal would likely decide the match. But during the time Portland also made a strategic move to try to press for the winning goal, by removing Thompson, and replacing him with midfielder Miguel Guante, leaving only one regular defender (Griffin) on the Timbers backline.

In the 70th minute, the visitors would lose one of their defenders as Nas Koubouras was carried off after Suzuki was fouled from behind and fell forwards into Koubourous’s legs. Ten minutes later, Hollywood United had a golden opportunity to take the lead when after a series of great touch passes, Dunseth played a nice diagonal chip to Mike Munoz (who had come on to replace Koubourous) who was in all alone, tapped the ball past the Timbers keeper and had an open net, but scuffed the shot and missed the goal completely, and the match remained level.

One minute later the Timbers would have a good chance to grab a late lead when Lara had an open look on a header that he put a few yards wide left.

Just before stoppage time, Hollywood United nearly stole the win as Boyce hit a surprising blast from 25 yards out that dipped only a hard over the bar.

With the match looking to go into overtime during three minutes of stoppage time, Hollywood United would steal the win as Taylor played a soft pass to second half substitute Earl Alexander, whose shot from 20 yards out deflected off the knee of Guante, and over James and under the bar and into the net, and the PGE Park crowd was shocked into silence as the visitors from California had taken a late 3-2 lead.

The Timbers managed a few deep crosses in stoppage time, but no more shots on goal, and at the final whistle, Hollywood United had pulled of a huge upset, but a deserved victory on the road against the Timbers, and go on to the second round of the US Open Cup.

Javier Barragan had five saves in the winning effort, while Jordan James had four saves in the losing effort.