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In a busy May when Minnesota United might play eight games, 90 minutes apparently wasn't enough Tuesday night at Allianz Field.

Neither was 120 minutes.

The Loons needed eight rounds of penalty kicks to finally defeat 2022 MLS Cup runner-up Philadelphia in a U.S. Open Cup victory that advances them to the all-comers tournament round of 16.

The teams played to a 3-3 tie before the Loons won 7-6 on the PKs with three extra rounds of duels between Union star keeper Andre Blake and Loons veteran Cliff Irwin.

"Never in doubt," Loons coach Adrian Heath said.

Union defender Kai Wagner forced both extra time and then penalty kicks when he scored very late goals in the 94th minute and 120th minute. He did so against a Loons team that gave up a goal on the last kick of the game for a 1-1 home draw with Vancouver in March and surrendered another very late one in a home loss to Orlando City last month.

Winless in their first four home games, the Loons gave themselves and their fans something to sing about finally when Irwin dove to his left to stop Wagner's penalty shot, the last of the night. Loons starting keeper Dayne St. Clair gave Irwin a tip before the final kick that Irwin wouldn't reveal afterward.

Until then, "Wonderwall" hadn't been heard at Allianz Field this season because the Loons hadn't won there. Tuesday they did, even if the announced crowd was 4,216.

Until Tuesday, Irwin had only heard it as a visiting keeper and only partially at that.

"I think I was in the tunnel already trying to get off the field," Irwin said about the only other times he had heard the Oasis song.

The Loons finally prevailed in eight rounds of penalty kicks after Irwin stopped two attempts, one more than Blake did.

"We were out there for a while," Irwin said. "But we were able to find the result and grind through it and just kind of ride the wave in this Open Cup competition, which always seems to throw some interesting challenges to you."

They did so after getting made PKs from center backs Brent Kallman, Michael Boxall and Micky Tapias, seldom-played Cameron Dunbar and Tuesday starter Joseph Rosales.

The Loons led 2-0 after 73 minutes and 3-2 in the 103rd minute after striker and second-half substitute Bongokuhle Hlongwane scored twice and did a lot of the hard work on Rosales' first goal as a Loon.

"Bongi gave us a real life when he came on," Heath said. "He might start listening to us about getting intom them one-touch finish areas as he did today. Him and Fraga [Franco Fragapane] really gave us a lift when they came on."

Heath called himself "pleased" for his players.

"It would have been a travesty if we hadn't won the game," Heath said. "It felt like we had to win three games, and the last kick of the game but twice. And then we showed a lot of character with the penalties because it's very easy to feel deflated when you concede the last kick of the game and we've done it twice tonight."

Wagner forced the game on twice, but coincidentally the game ended when he couldn't convert his penalty kick right after Tapias made his.

"He's fantastic on dead balls," Heath said of Wagner. "He's got a wonderful left foot…I'm pleased for Clint. He showed great character."