Despite the Timbers being the #1 seed in the tournament, it was the visitors who nearly took the lead in the 5th minute when after a corner kick by Reading was not cleared by the Timbers defense, midfielder Luke Mulholland's header was cleared off the line by Portland's Brian Ramsey. The Timbers had their first good chance in the 13th minute when Bim Ogunyemi made a run down the right side, his cross finding Ramsey charging the near post, but his attempted flick-on was blocked by the Reading defense.

In the 18th minute, the Timbers had another good look when a corner kick was passed directly to Brent Richards at the top of the Reading box, but his high blast was saved by Reading goalkeeper Jeremy Vuolo. Five minutes later, it was Reading with a good chance when CJ Sapong made a run into the Timbers box, and his shot towards the lower left side of the net being pushed wide by Timbers goalkeeper Jake Gleeson. Two minutes later, the visitors had another good ahcne when Levi Houapeu cut back from a run down the left side and had an open look at net, but his shot was right at Gleeson.

Shortly afterwards, at the other end of the pitch, it was the Timbers with a great chance off a long throw-in by Richards that bounced through the box and was trapped and cleared off the line by Corey Hertzog. And just a minute later, the Timbers had a good free chance opportunity just outside the Reading box, but the kick by Roberto Farfan was right at Vuolo.

In the 29th minute, Reading's Sapong took a chance on a long shot from 35 yards out as he found some space, and his dipping shot was just a yard or two wide left.

In the 40th minute, the Timbers had an apparent goal ruled offside, and two minutes later, it was Sapong once again taking a chance from distance, with a 25 yard blast that was well over the bar. Reading had a few dangerous crosses into the box in first half stoppage time that the Timbers cleared, and it was 0-0 at the half.

Just three minutes into the second half, the Timbers would break the scoreless deadlock when Ramsey fought off the challenge from defender Adam Welch, and crossed to the far post Jon Ports could not clear it, and Ogunyemi jumped on the loose ball and blasted the ball just inside the left post and into the net to give the Timbers a 1-0 lead. One minute later, Portland's Tracy Hasson made a nice turn near the corner of the Reading box, but his curling shot was a few yards over the crossbar.

In the 56th minute, the Timbers had a good chance to widen the score when a header from Freddie Braun was saved by Vuolo, and then on the counterattack, Supong made a nice run into the Timbers box, but was forced wide by the retreating Timbers defense, and ended up shooting wide right from a tight angle. Three minutes later, Reading had another good chance when a free kick was headed just wide left by Welch.

In the 65th minute, the Timbers nearly doubled their lead when Richards stole the ball from the last Reading defender, but his first touch as he attacked failed him, as he pushed it too far forward and Vuolo was able to come off his line and smother the ball. Five minutes later, the visitors had another good chance to level, but Sepong's shot from inside Timbers box was blocked wide left off a Timbers defender.

In the 73rd minute, the Timbers appeared certain to widen their lead to two goals when after Ogunyemi's shot was saved, Richards had a chance on a rebound that Vuolo blocked but did not cover, and Richards had a final chance at an apparently mostly empty goal, but his final attempt was off the crossbar.

But after the ensuing goal kick, Reading United did not take long to punish the Timbers for the missed chance when Sapong made a deep run down the right side, and crossed to Houape who one-timed the shot into the lower left corner, and the partisan home crowd has been silenced as Reading had drawn level at 1-1.

But it wouldn't last for long, as only about a minute later, Timbers forward Ricky Abrego, who had only been on the pitch for a few minutes, dropped a pass from inside the Reading box to a charging Braun at the top of the box, and his blast to the lower left corner of the net slipped just past Vuolo and settled into the back of the goal, and the Timbers were once ahead in the lead, by a 2-1 score.

Reading had a few dangerous free kicks late taken from just outside the Timbers box, the most dangerous being in the 84th minute when a free kick by Mulholland from 30 yards out slipped just past the left post.

The Timbers had several late chances to widen the lead as Reading was pushing their defenders forward, with Abrego breaking through in the 90th minute but Vuolo aggressively smothering an attemped pass to an open Richards, and then Richards breaking in alone a minute later, with Vuolo once again up to the task and smothering the shot. But in the end, the insurance goal was not needed, and the Timbers held on for their third consecutive 2-1 win, and a trip to the PDL Championship game for the first time.

Jake Gleeson had three saves for the Timbers in the winning effort, while Jeremy Vuolo recorded four saves for Reading.