The Timbers started a nearly all reserve lineup, with the only regular being defender Stephen Keel. Neither team had a good chance until the 10th minute, when Puntarenas' Ricardo Garcia made a nice run down the right side, but his tight angle shot was saved by Timbers goalkeeper Matt Pyzdrowski. The Timbers then nearly scored on an ensuing counterattack when Takayuki Suzuki had a good look from the top of the box, but his shot was just wide left. In the 16th minute, it was Portland's Alex Nimo also made a deep run, with his low shot being saved by goalkeeper Bryan Zamora.

But five minutes later, another deep run would pay off for the Timbers, this time by forward Bright Dike, who had a deep run down the right side, then cut back onto his left foot, and hit a left-footed blast from 15 yards that was inside the left post, and the Timbers had an early 1-0 lead. Three minutes later the Timbers nearly doubled the lead when Nimo played a nice pass to Doug DeMartin, but his shot was saved, and though the ball was loose briefly, the Puntarenas keeper was able to recover just quickly enough to prevent a follow up shot.

The Timbers were getting lots of chances during this stretch, with defender Scot Thompson coming forward on a nice run down the right side and getting a shot from near the corner of the box that forced a diving save from Zamora to push it wide. Off the ensuing corner kick, Timbers midfielder Tony McManus had a good look, but pushed his shot wide left. Shortly afterwards, Dike made a nice run down the left side, crossing to Nimo, whose header was saved easily by Zamora.

The visitors didn't have many chances on the night, but made their next good chance pay off when Gabriel Masner chipped the ball into the run of Pedro Leal, and with Pyzdrowki coming off his line to cut the angle, Leal beat him to keeper's left to level the score at 1-1.

In the 36th minute, the Timbers would nearly retake the lead when Thompson got his head on a corner kick, but his shot was a few yards over the bar. It would be the last good chance for either team, and the score would be level at the half.

It wouldn't take long for the Timbers to start a siege on the visitors goal, with Dike making a nice diagonal run into the box in the 47th minute, but his first touch failed him and the Puntarenas goalkeeper was able to smother the ball. Shortly afterwards, DeMartin had a good look from the top of the box, but the Puntarenas keeper was again up the task, and within a minute, it was Suzuki with a good look but his shot was just over the bar. Suzuki had an even better shot in the 52nd minute, but his shot was off the left post.

As it happens, Puntarenas would turn their first chance of any kind in the second half into a lead, when Garcia made a run down the right side, lobbing a pass into the path of Joshua Diaz, who hit a brilliant full volley in full stride that was just inside the right post, and the visitors had taken a 2-1 lead very much against the run of play.

But it wasn't over, when just three minutes later, on the only other chance of the half, they doubled their lead when the Timbers gifted them a goal with a back back pass from Thompson which was intercepted by Daniel Pena, and chipped over Pyzdrowski and into the net for a 3-1 lead.

The rest of the match would be a continuing siege on the Puntarenas goal, especially in the last 20 minutes. In the 69th minute, OJ Obatola made a nice deep run to the end line, but his chip across the open goal mouth went harmlessly though and was cleared. In the 80th minute, off a Timbers corner kick, with a DeMartin shot after a failed clearance being saved at the post by a spectacular save by goalkeeper Olger Ruiz. Two minutes later, it was a header from McManus that was just over the Puntarenas goal.

In the 86th minute, substitute Mandjou Keita, seeing his first action this season, nearly made a spectacular side flick off a cross but it was right at Ruiz and easily saved. The last good chances for the Timbers would be three minutes later when a header by Mamadou Danso off a corner kick slipped just a yard past the left post, and then a dipping shot by Quavas Kirk was smothered by Ruiz.

But all the Timbers chances only resulted in a single goal, so the Timbers would fall to their Costa Rican visitors by a 3-1 score.

Matt Pyzdrowski had two saves for the Timbers while Jake Gleeson recorded no saves. Bryan Zamora had six saves for Puntarenas FC while Olger Ruiz had three.