Chicago Fire Face Former Striker Hugo Cuypers In Leagues Cup Quarterfinal

Chicago Fire FC are the only MLS team to win all three of their Leagues Cup group games outright, and on Tuesday night they face a Monterrey side led by the striker they let go a few weeks ago. For Gregg Berhalter, the buildup to the quarterfinal has doubled as an ongoing tribute to Hugo Cuypers, even as his current squad keeps proving it can win without him.

A statement win to close out group play

Chicago capped a perfect group stage with a 2-1 win over Liga MX powerhouse Cruz Azul on Aug. 13, a result that sent the Fire into the knockout rounds as the only club to take maximum points from Phase One. It followed a 2-0 opening win over Club Necaxa and a come-from-behind 3-1 victory over Santos Laguna, in which Chicago scored three unanswered goals in the second half after trailing at the break. Cruz Azul, the defending Liga MX champions, arrived unbeaten in their first two Leagues Cup matches, having already beaten New York City FC and the Philadelphia Union.

“We knew the implications of the game,” Berhalter said afterward. “Everyone knew the implications of the game. Cruz Azul did as well. So for us, it was we need to advance.”

“It’s a strong team, and they didn’t win the championship for no reason,” he added. “For us, it was a good challenge. I told the guys, we signed up for this. This is why we’re all here, to play games like this. We won one of them, but we’re gonna win more, and if we win more, then we’ll do good things.”

Dithejane’s breakout continues

The win over Cruz Azul was built on a pair of goals from Puso Dithejane, the South African forward who has become an increasingly important piece of Berhalter’s attack after arriving from TS Galaxy over the winter as a U22 Initiative signing. Dithejane got on the end of a loose ball in the box to put Chicago ahead, then slotted home a pass from Maren Haile-Selassie in second-half stoppage time to break a 1-1 deadlock and seal the win.

Dithejane, 22, joined Chicago in January of last year from TS Galaxy of South Africa’s Betway Premiership, occupying both a U-22 Initiative slot and an international roster spot on a contract that runs through the 2029-30 season with a club option for a further year. A right winger by trade who can also play at right back or in attacking midfield, he made his senior debut for South Africa’s national team, Bafana Bafana, in 2023 and has continued to earn caps at international level while establishing himself in MLS.

It capped a run of form that has made Dithejane essential to how the Fire play. Berhalter singled him out as the club’s coach’s man of the match against Cruz Azul.

“We see it every day in training, we see what he does,” Berhalter said. “When we came back from the World Cup break, we had a chance to go home, and we played a couple friendly games and we’re training, and every day he’s scoring goals. He’s a dynamic player and gets in good spots. He still needs to develop and still has got a long way to go, but there’s a ton of potential in him and happy for him.”

Berhalter’s project taking shape

Berhalter took over as Chicago’s director of football and head coach in October 2024, his first return to club soccer after a spell at Columbus Crew that ran from 2013 to 2018. He arrived in Chicago with three major trophies on his resume from his time in charge of the U.S. men’s national team, including the 2021 Concacaf Gold Cup and two Concacaf Nations League titles, plus a Round of 16 finish at the 2022 World Cup. The Fire became his 10th head coach in club history when they hired him, and results like the perfect Leagues Cup group stage are the clearest evidence yet that the rebuild he was brought in to lead is starting to produce results on the field, not just on the recruiting trail.

Facing the striker they sold

Tuesday’s quarterfinal at SeatGeek Stadium carries an added layer for Chicago given who is waiting across the field. Monterrey signed former Fire striker Hugo Cuypers in July for a reported $7.5 million fee, at a point when he was sitting atop the MLS Golden Boot race. Cuypers had been a central figure in Chicago’s attack before the move, and Berhalter made clear the club has not forgotten what he gave them.

“Of course, right? Of course it turned out like that,” Berhalter said of facing his former striker so soon after his departure. “Monterrey’s a good team. It’s gonna be a good competition. It would be nice if we could do something for Hugo, honor him in front of the fans. He was a big part of what we were doing here. Now he’s enjoying Monterrey, scoring a bunch of goals, and they’re going to be a good opponent.”

Cuypers is not the only familiar face on the opposing bench. Former Columbus Crew forward Diego Rossi has also contributed a goal and an assist for Monterrey in the competition, giving the Liga MX side two attackers with recent MLS pedigree feeding off knowledge of how their old league’s teams like to play.

How Leagues Cup works

Leagues Cup pits all 18 MLS clubs against all 18 Liga MX clubs in a cross-league format that replaces a chunk of the regular MLS regular-season calendar each summer. Teams play three group matches against opponents from the other league before the top finishers advance to a straight knockout bracket, giving MLS sides a rare chance to measure themselves directly against Mexican opposition outside of the Concacaf Champions Cup.

For MLS clubs, the competition also offers a chance to lean on Designated Players like Lewandowski in high-stakes games against Liga MX sides that are generally built without the same roster-construction rules MLS teams operate under, making a deep run a genuine measuring stick for a club’s ambitions.

A dangerous draw either way

Monterrey reached the quarterfinals as one of Liga MX’s traditional powers, and Chicago’s own path through the group stage, beating Necaxa and Santos Laguna before that statement win over Cruz Azul, suggests this quarterfinal will not be an easy step up in class so much as a genuine collision of two sides playing with confidence. Kickoff is set for 7:30 p.m. CT at SeatGeek Stadium in Bridgeview, Illinois.

Chicago’s summer additions have raised expectations well beyond a top-half MLS finish. The club signed Robert Lewandowski as a free agent Designated Player on June 29, 2026, after the Polish international’s contract at Barcelona expired, handing him a two-year deal that runs through the 2027-28 MLS season and, by most reports, the second-highest salary in the league behind only Lionel Messi. Berhalter has said the club worked to bring Lewandowski to Chicago for roughly a year and a half before the deal came together.

That signing, combined with a squad already sitting inside the top three of the Eastern Conference table over the summer, has results like the perfect run through Phase One of Leagues Cup pushing Fire supporters to think seriously about a run deep into the knockout rounds this year.

What a win would mean

A victory over Monterrey would send Chicago into the Leagues Cup semifinals and hand Berhalter’s team a chance to measure themselves against one of Mexican soccer’s most established clubs at a point in the season when Chicago’s own form is peaking.

For Berhalter, the emotional subplot around Cuypers will not change how his team approaches the game. Chicago have shown throughout Phase One that they do not need one player, however important, to keep scoring goals, with Dithejane, Haile-Selassie and others sharing the load in his absence. But there is little doubt the Fire’s head coach would enjoy nothing more than sending his former striker out of the competition in the process of proving exactly that point.

“Monterrey’s a good team,” Berhalter repeated when asked to preview the matchup. “It’s gonna be a good competition.” Whether that competition ends with Chicago advancing to a Leagues Cup semifinal, or with Cuypers getting the better of the club that developed him, Tuesday’s meeting promises to be one of the more compelling storylines of this year’s knockout rounds. For a Fire team that spent years rebuilding around a coach with an international pedigree and, more recently, a Designated Player capable of drawing global attention to SeatGeek Stadium, a run through the rest of August offers a chance to show that both investments are finally paying off at the same time, in front of a home crowd that will be watching every touch Cuypers takes in a Monterrey shirt.