It’s been a busy few weeks for your Loons, and tonight they returned to their home away from home (the West Coast) for yet another midweek matchup. Unfortunately, they wouldn’t find the same results they cultivated in their last several stints in California, but the night’s Round of 16 match was still packed with undeniably engaging soccer.

Cameron Knowles put forward a rotated lineup in the Round of 32 against Sacramento, but to take on the best squad in Major League Soccer, this time he opted for the starting lineup that won the Loons so many regular-season matches in a row. Most notably, Drake Callender started in net rather than Alec Smir, and the productive front trio of Tomás Chancalay, Joaquín Pereyra, and Kelvin Yeboah took to the pitch right off the bat.

San Jose pulled no punches either, playing superstar Timo Werner along with high-scorers like Preston Judd and Niko Taskiris. Each side pulled out all the stops for this match, and for good reason — both Black and Blues came out with fervor, with Minnesota going for a goal right away with a Nectarios Triantis shot in the third minute, saved by Daniel De Britto Sousa (known simply as Daniel, like Beyoncé). The Loons controlled the ball for most of the first 15 minutes, with midfielder Owen Gene doing particularly well on the defensive end even against the fancy footwork of Ousseni Bouda.

In the 15th minute, San Jose broke the scoring wide open when Werner leveled a great ball over to Judd. A miscalculated touch by Gene allowed Beau Leroux to dart into the opening with a decisive double touch and a lethal shot that put the Quakes on the board. The initial goal was proof that against the powerhouse that is San Jose, all it takes is a half-second mistake.

The rest of the half passed in a back-and-forth flurry of corners and dangerous attempts in both boxes, with Callender holding down the fort and some graceful combination play from the front three and a handful of defenders who drifted forward to get in on the offensive action. Anthony Markanich, Jefferson Diaz, and Nicolás Romero all logged shots in the first 45 minutes. Romero’s shot, born of smart positioning and a great touch from Triantis, found the back of the net in the 31st, though Romero was found offside.

One minute later, Werner went down with a potential hamstring injury and was replaced by Jack Skahan,  a big hit to San Jose’s offense. Despite the loss, the Quakes — whose roster depth is quite impressive — kept engineering opportunities, but Minnesota met them at every turn and hung onto 57% possession. 

Paul Marie replaced Judd for San Jose at the half, while Minnesota made no changes and came out swinging. Their aggressive approach yielded a fantastic trio of chances from Chancalay, Pereyra, and Romero within the first 10 minutes of the second half. San Jose’s runs, though dangerous, were few and far between as the Loons kept the home team in their own defensive third for long stretches.

Their aggressive approach paid off in the 59th minute, when a clever Pereyra touch made space for Triantis to make a mad dash up the right flank, crossing the ball to a waiting Anthony Markanich. Though it went into the books as an own goal on Ronaldo Vieira, the credit for that equalizer should go to the wingback who always knows exactly where to be. 

A few minutes later, Markanich saw an opening to get the ball to Chancalay, who made a powerful run forward, artfully outmaneuvered Benji Kikanović, and nailed it all the way to the far post to take the lead. 

With the scales tipped in Minnesota’s favor and under half an hour left on the clock, the Loons seemed ready to cruise all the way to the quarterfinals and shut down San Jose on their home pitch. But with the Loons clustered in the box after a San Jose corner kick, Skahan took advantage of a lapse in defensive judgment to send the ball past Callender in the 68th minute, setting the scoreline level once again. 

A 65th-minute substitution of Devin Padelford for Romero and a pair of late wingback substitutions substantially rearranged Minnesota’s defensive shape, creating some confusion in terms of defensive possibilities that San Jose readily seized. With the Quakes’ energy renewed, they made an aggressive push forward in the 73rd minute as Minnesota’s defense started to become scattered. A long ball up to Skahan was delivered to open Leroux, who was ready to bag the brace and put the home team back in the lead.

The momentum was now firmly shifted in favor of the home squad, and with the Loons forced to aggressively throw numbers forward, Bouda and Tsakiris made a mostly uncontested run to bag goal number four, with Bouda drawing Callender out of goal and Tsakiris ready for the pass. After a long stretch of Minnesota domination, something had awoken in San Jose, and the final moments of this match were firmly San Jose’s. Even a late substitution of James Rodríguez, whose long Hail Mary shot in stoppage time sailed a bit too high, wasn’t enough to take back the lead against the Quakes. 

The disappointing scoreline means Minnesota is out of the Open Cup runnings this year, and the devastation of a tournament knockout is no small thing. The Loons will have to wait yet another year for their shot at U.S. Open Cup glory, but in terms of consolation prizes, it was a valiant fight against an MLS giant. Tonight was by far the most aggressive performance we’ve seen from the Loons this year, and proved for long stretches that Minnesota can hang with (and at times, even outplay) the best of the best. That kind of offensive energy translating into regular-season play could be a major silver lining, as long as the Loons can straighten out their defensive miscues while maintaining their newfound on-the-ball energy.