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2025 US Open Cup Round 5: Jack Skahan’s OT winner sends San Jose Earthquakes past Timbers

May 21, 2025 by Connor Bunnell

Jack Skahan (center) of the San Jose Earthquakes celebrates with his teammates after scoring a goal against the Portland Timbers in the Fifth Round of the 2025 US Open Cup. Photo: San Jose Earthquakes - ISI Photos
Jack Skahan (center) of the San Jose Earthquakes celebrates with his teammates after scoring a goal against the Portland Timbers in the Fifth Round of the 2025 US Open Cup. Photo: San Jose Earthquakes – ISI Photos

It was a classic case of “Open Cup After Dark” in the Bay Area at Paypal Park on Tuesday night, as the San Jose Earthquakes bested the Portland Timbers 1-0 in extra time.

The opening minutes set the tone for a fast and fluid game in the Round of 32 match in the 2025 Lamar Hunt US Open Cup, with Portland choosing a direct and physical approach and taking the first shot of the night. However, San Jose soon established themselves as the team with the bulk of possession and control of the game’s flow. Time after time, they got into threatening areas and made noise, particularly in the area directly to the right of the box.

However, once it was time to finish their plate, the Quakes proved squeamish eaters. Despite taking ten shots to Portland’s five in the opening 45, only Carlos Espinoza’s attempt in the 30th came close enough to force Maxime Crépeau’s hand. The other nine all sailed harmlessly wide and/or into the stands. Meanwhile, on the other end, only Ariel Lassiter could put his shots on target, and Earthquakes captain and goalkeeper Earl Edwards Jr. thwarted both attempts, ensuring things went scoreless into halftime.

Upon returning from the break, the Quakes came out guns blazing, and their accuracy had certainly improved. In just over ten minutes, they made Crépeau spring into action for a save three times. Much of San Jose’s confidence and willingness to challenge up front stemmed from knowing how stellar they were in defense. Center back Daniel Munie, in particular, was on fire all night, making clearances and winning duels for possession practically every time his team needed him to.

The Timbers, on the other hand, seemed more desperate by the minute despite doing a decent job keeping a lid on the incoming attack. While the fouls certainly flew both ways, Portland gave away more of them, and that behavior came to a head in the 86th minute. With Espinoza on the run and heading for the right side of the box, Kamal Miller brought the Quakes’ all-time assists leader down right at the edge of the penalty box.

The refs’ decision on it managed to anger both sides of the aisle — so many Timbers swarmed and argued it wasn’t a foul that two got yellow cards for arguing, while Bruce Arena and the home crowd were livid when it turned out to be a free kick and not a penalty.

Espinoza’s ensuing shot went straight to Crépeau, as a group of children in the crowd chanted “Ref, you suck!” in the aftermath. After 90 minutes plus six more minutes of stoppage time, the scoreless duel officially needed extra time to settle it.

The next 15 minutes were, from a possession perspective, San Jose’s most dominant run, as they kept the ball for 65% of that half. However, it seemed that no matter what the Quakes did, they just couldn’t thwart the Quebecker in net, as Crépeau came up with saves number six and seven of the night. By the time of his eighth in the second half of extra time, the possibility of penalty kicks was looking more like a certainty.

However, in the final five minutes, the Earthquakes finally made true headway when Mark-Anthony Kaye made an interception deep in Timbers territory and dished it to Preston Judd, who made his run toward the box, then sent a through ball to the left side where Kaye could meet it. The Canadian took his first touch, lured Crépeau forward, then fired towards the far post. After that, Jack Skahan applied the finishing touch, and the north end’s Seismic Union and south end’s San Jose Ultras, who’d each spent the night drumming and chanting with no regard for each other, united with all the home fans in between to send up one big scream of joy. Finally, after all that toil, San Jose had their goal.

“Preston did a really good job to hold the ball up,” Kaye told reporters after the match, “and I realized that if I made a run for it, he’d play me into the box. My first touch took me a little wide, but I knew that if I (could) just get the ball into the area, my teammate would put it in. I’m happy for Jack, that he was able to score. He’s been working really hard, and guys like that deserve the spotlight.”

With just a few minutes to respond, and many of those precious seconds eaten up by San Jose’s attempts to double their advantage, Portland scrambled to try and send it to penalties. Despite putting up some decent long balls, their last shot courtesy of Ian Smith went harmlessly into Edwards Jr.’s hands.

Upon the final whistle, the Earthquakes clinched their first trip to the Open Cup quarterfinals since 2017. It also extended San Jose’s home winning streak in the competition to eight games, which is tied for the fifth longest streak of the Modern Era (1995-present). The Quakes’ last home loss in the Open Cup was a 1-0 loss to the LA Galaxy in Fifth Round in 2015. The Galaxy’s head coach that night? Bruce Arena.

Head coach Bruce Arena was candid about the significance of reaching this stage.

“When I was with the LA Galaxy,” Arena said, “ … our goal was to win the MLS Cup and/or Supporters’ Shield. That’s where that club . This club is not there. This club has not achieved much over the last X number of years, however you want to define that, and I think this is an important competition to start getting back to winning ways and being a club that’s more respected competitively.”

With this result, the Earthquakes are now undefeated in their last six matches across all competitions. This also marks their first Open Cup win over the Timbers since 2005, when the latter were still playing in the USL.  San Jose’s next Cup match will take place on July 8 or 9 when they host Austin FC.

 

Filed Under: 2025 US Open Cup, US Open Cup, US Open Cup Central Tagged With: 2025 US Open Cup, Portland Timbers, San Jose Earthquakes

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