The Italian youngsters showed a great deal of passing skill on the PGE Park turf, and would produce the first good scoring chance in the 10th minute when Enrico Travaini slipped in behind the Timbers defense, and was only denied a good scoring chance by a retreating Cameron Knowles, who chased him down and knocked the ball loose at the top of the box. Four minutes later, there were many anxious moments in the Timbers box as the ball was knocked free when Timbers goalkeeper Bayard Elfvin collided with an AC Milan player and lost control of the ball, but the eventual shot that would get on net, from midfielder Ferdinando Vitofrancesco, was saved by Elfvin.

The Timbers first good look would come in the 23rd minute when Lawrence Olum had an open look from about 20 yards out, but his blast was 2 or 3 yards over the crossbar.

But two minutes later, the Timbers would take the lead when midfielder Tom Taylor worked a give-and-go with forward Jaime Ambriz and found himself open in the box, and slotted a low shot to the far side and past AC Milan goalkeeper Daniel Offredi to give the Timbers a 1-0 lead.

One minute later, the visitors nearly equaled when Vitofrancesco had an open look from 15 yards out, but his high blast was knocked over the crossbar by Elfvin.

In the 35th minute, the AC Milan Primavera side would be on the attack again, and a low cross from Kingsley Umunegbu to Travaini gave him an open shot from the top of the box, but was right at Elfvin for the easy save. Two minutes later, the visitors had their best chance of the half when a cross from Davide Rampinini had Travaini open less than 10 yards out from goal, but badly mis-hit the shot wide left, and the half would end with the Timbers holding a 1-0 lead.

AC Milan Primavera would come out on the attack in the 2nd half, and just two minutes later, Enrico Da Ros made a nice run to the left post and had a great chance go begging when his shot from 6 yards out was into the side netting.

In the 56th minute, the Timbers had a great chance to widen their lead when a cross from Ambriz found David Hague open near the penalty spot, but this shot was just wide left.

But shortly afterwards, the complexion of the match would change drastically when Timbers midfielder Andrew Gregor was shown a red card, apparently for his comments to center referee Alejandro Mariscal, and the Timbers would have to attempt to hold their lead while down a man for the final 34 minutes.

They would only manage to maintain their lead for 10 minutes as Traviani slipped into the Timbers box with some fancy footwook and softly chipped the Timbers goalkeeper as he came off his line to even the score at 1-1.

The Timbers would have their best chance to steal a late win in the 80th minute when a though ball to Timbers forward Luc Harrington had him briefly in alone on the Italian keeper, but Harrington was unable to control the ball on his feet and an AC Milan defender was able to recover in time to stop the breakaway near the top of the box.

Just as the match entered stoppage time, the visitors would have a great chance to steal the late win themselves when Umunegbu was open in the Timbers box, but hit a weak shot that was easily saved.

The teams had decided that penalties would be used to resolve a draw before the match had started, and it would be the Timbers who would shoot first in front of the Timbers Army at the north end of PGE Park.

Portland’s Leonard Griffin would shoot and score first, while Alex Guerci put his shot off the crossbar for the miss. In the second round, Harrington put his shot inside the right post while the Italians would again miss, with Alessandro Cattlehan sliding his shot just outside the right post.

The Timbers would again score in their third shot, with Kiki Lara putting his PK in easily, with Matteo Bruscagin answering to keep AC Milan alive in the shootout. But that would not last long as Portland team captain Lee Morrison would put home the fourth Timbers PK to give them a 4-1 PK victory.

Bayard Elfvin was credited with four saves for the Timbers while Daniel Offredi was credited with no saves for AC Milan.