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Cuypers vs. Lewandowski Headlines Epic Chicago Showdown

The storylines wrote themselves when Chicago and Monterrey found out they would face off in Leagues Cup.

Hugo Cuypers and Robert Lewandowski score goals in Leagues Cup.
(photos: Leagues Cup, Barbara Calabrese)

A month ago, it was Hugo Cuypers and Robert Lewandowski.

But today, it’s Hugo Cuypers vs. Robert Lewandowski.

Exactly 33 days after Cuypers was unveiled as a new CF Monterrey player, MLS’ biggest transfer story of the summer gets an unexpected additional chapter. The 29-year-old striker, who at the time of his Chicago exit was leading the league in goals, has returned to the Windy City for a highly anticipated Leagues Cup quarterfinal showdown with major CONCACAF Champions Cup implications.

From a Chicago standpoint, that makes Cuypers the villain and Lewandowski a potential hero. Only one can advance to next week’s semifinals.

“We knew it was always going to be Hugo coming back to Chicago, right?” Head Coach Gregg Berhalter said on Monday. “No matter what, with the way fate works out. But Hugo’s been great. He was great for us. It was great to work with Hugo.”

“I think I shared many times openly about our relationship, how good it was, and how much he meant to us as a coaching staff. So it’ll be nice to welcome him back.”

Just last October, Cuypers scored twice at SeatGeek Stadium to hand the Fire their first playoff win in 16 years. On Tuesday, he returns to the same field with an opportunity to eliminate them from another important knockout competition.

Hugo Cuypers scores against Orlando City in the MLS Cup Playoffs of 2025.
Last season, Cuypers was the Fire's playoff hero in Bridgeview. (photo: Barbara Calabrese/MIR97 Media)

Cuypers’ exit came suddenly and unexpectedly in July. The striker was in fine form for the Fire and had, at least publicly, welcomed the arrival of Lewandowski. Cuypers had announced a switch to the #99 shirt to make way for the new superstar signing, and the club posted a video of him sharing his excitement about playing alongside the two-time FIFA men’s player of the year.

The club was also prepared for life with two center forwards; Berhalter had spent months preparing the team to play in a two-striker setup, with the clean plan being to pair Cuypers with Lewandowski.

But Cuypers handed in a transfer request shortly afterward. While Lewandowski was making his MLS debut at Inter Miami, the Belgian was on a plane to Monterrey to finalize his move south of the border before revealing that he would conspicuously wear the same #99 shirt he had initially agreed to take in Chicago.

“I think everybody knows the situation in Chicago with Robert arriving,” Cuypers said earlier this month in an interview with Apple TV. “I think there was a scenario where everything was working out well, and we could have played together, but there was also a scenario where he would have been the main guy in the short or medium term. I didn’t want to take that risk.”

That broadcast interview is the only interview Cuypers has done with U.S. media since Lewandowski signed. Monterrey staff informed local media on Monday that, despite a scheduled Rayados mixed zone, the former Fire talisman would not be available to answer questions ahead of his return.

Hugo Cuypers playing for Chicago Fire in 2025.
Cuypers had led MLS in goals until last week. (photo: Barbara Calabrese/MIR97 Media)

Monterrey also trained at the University of Illinois-Chicago, declining to use the Fire’s downtown training facility as has been customary for traveling teams throughout Leagues Cup.

As a result, Cuypers will return to Chicago without answering questions from Chicago media about the circumstances of his departure or the prospect of facing his former club. From a Fire standpoint, that only adds to his status as Tuesday’s antagonist.

On the other side will be Lewandowski, whose arrival has been debated by Fire fans since June, largely because of what it could mean for Cuypers. Just a few short weeks after the two were supposed to lead the line together, they will be tasked with ending the other’s Leagues Cup run.

So far, Cuypers and Lewandowski have matched each other at their new clubs. Both have started all but two of their respective team’s games since the World Cup break, and both have scored exactly four times.

Robert Lewandowski against the Portland Timbers, playing for Chicago Fire FC.
Lewandowski has been Chicago's talisman since arriving. (photo: Barbara Calabrese/MIR97 Media)

It also hasn’t been perfect for either; Lewandowski has balanced strong performances against Charlotte, Necaxa, and Orlando with relatively anonymous outings against NYCFC, Santos Laguna, and New York, while Cuypers scored in all three Leagues Cup games but struggled mightily in a 2-0 loss to León on Saturday. In spite of all that, both strikers have given their new teams reasons to be encouraged; Cuypers is providing goals for Matías Almeyda, and Lewandowski is emerging as the face of Berhalter’s ambitious project.

The stakes extend beyond just a semifinal berth. Neither club has qualified for next year’s CONCACAF Champions Cup, and a top-three Leagues Cup finish would guarantee either team a place. While the strikers will get the headlines for obvious reasons, what makes the matchup particularly intriguing is the sheer quantity of talent across the pitch on both sides. 

The Rayados roster includes 11 capped Mexico internationals, most notably Tecatito Corona, Gerardo Arteaga, Orbelín Pineda, and Fidel Ambríz, as well as former MLS Best XI stars Luca Orellano and Diego Rossi. The Fire come in riding a seven-game unbeaten run, with the likes of Puso Dithejane, Philip Zinckernagel, and Djé D’Avilla finding top form.

Lewandowski celebrates his goal against Santos Laguna.
Vibes are high in Chicago after a six-game winning run in August. (photo: Barbara Calabrese/MIR97 Media)

“I think when you look at the depth of their attacking pieces – whether it’s Hugo or Rossi or Ocampos or Corona or Pineda – they have a number of players that can hurt you,” Berhalter said. “The game is never just about two players. There are going to be 20 other players on the field. The game will be decided by what team can execute better.” 

“As I said, we know they’re a good team, and they can cause us problems, so just be aware.”

While the quarterfinal will ultimately be about more than just the two star strikers, the storyline is clear: Cuypers left Chicago because he did not want to compete with Lewandowski.

Now, with a semifinal berth at stake, that is exactly what he will have to do.

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