The storylines couldn't be better if you wrote them: Just when it felt like Cruz Azul, one of the top teams on the continent and the reigning Liga MX champions, were willing to settle for a draw with the Fire at SeatGeek Stadium that would see both teams progress, a quick moment of pressing from the Mexican side left a defensive gap that became a moment of brilliance from Puso Dithejane.
The win was the Chicago Fire's first victory over a Mexican side in over a decade and a half, cementing the Fire's record in the first stage of the tournament as the only MLS side with a perfect nine points.
In felling one of Mexico's giant clubs, however, they set up a date with another: In the single-elimination quarterfinal, the Fire would face CF Monterrey, the new home of Hugo Cuypers after he left the Fire in the midst of a season that had him on the inside track to become the first accolade winner the Fire have had in nearly a decade.
"We knew it was always going to be Hugo coming back to Chicago, right?" Fire Head Coach Gregg Berhalter pondered at a press conference on Monday afternoon. "No matter what, with the way fate works out."
Despite being the rapid nature of the departure – with Berhalter laying the way to play Cuypers alongside Robert Lewandowski – Berhalter has gone out of his way to stress not only the lack of ill will, but also, the esteem that the Belgian still holds with the club: After the victory over Cruz Azul, he openly pondered whether the club could do something to commemorate the departed player's time with the club.
On Monday, Hugo's been great. He's been 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."
That may be – on Tuesday night, either Berhalter's team or Cuypers's will be heading to a semifinal and a chance to clinch a CONCACAF Champions Cup spot next year, while the other will leave disappointed.
CF Monterrey
CF Monterrey are a club with acres of depth – and the weight of disappointment, particularly after a disappointing Clausura campaign in the spring that left the team 13th in the league.
To remedy things, the team has overhauled the squad and brought in Argentine Matías Almeyda, who was most recently the coach of Sevilla in La Liga. He is probably best known to fans around the league for having coached the San Jose Earthquakes from 2018 through early in the 2022 season.
Despite the poor performance of their last season, the squad is deep and full of talent, including figures like Jesús "Tecatito" Corona, Oberlin Pineda, and Lucas Ocampos. They've bolstered the squad in no small part by looking north of the border: In addition to Cuypers, Rayados brought in Diego Rossi from the Columbus Crew, and Luca Orellano arrived from FC Cincinnati in January.
In case the list above – from Tecatito to Ocampos ‒ didn't drive the point home, the depth of Monterrey's attack on is significant, with Berhalter noting that while "Cruz Azul is good... I didn't think their attacking quality was of the caliber of Monterrey, so it's something we're going to have to be aware of."
Chicago Fire
Although the Fire's winning streak may be over, the undefeated streak continues. The team's current record winning streak during their inaugural 1998 season included a win in PKs, at a time when the league did not have draws.
That echoes the format of this game, which, if tied after regulation, will go to penalties just as those games in MLS's early years did.
The knockout format poses a key question for Berhalter on how to use his squad.
On Saturday night, many normal key players were given time off: Andrew Gutman, the Fire's ironman in 2025, did not play at all.
Others were given shorter minutes than usual: Philip Zinckernagel, who leads Fire outfield players in minutes in 2026, was relieved in the 65th minute, at which point Anton Salétros and Robert Lewandowski were subbed on.
Jack Elliott, Djé D'Avilla and Puso Dithejane, meanwhile, were given short cameos late. Dithejane's rest ahead of this key match may be the clearest indication we've had yet of where he stands in the Fire's depth chart after his recent performances.
The rotation has given key parts of the Fire's squad about as much rest as would be practical considering the team's packed schedules in the weeks leading up to this game.
Still: The team has had a ton of minutes put on their legs, individually and collectively. This will be the Fire's eighth game in August, with a ninth scheduled across the continent in Seattle on Saturday.
The rotation has given more of his squad real minutes – and confidence. "We'll have a number of guys that will go into the game with confidence," Berhalter said on Monday, "confidence in what type of form they're in. And it won't just be the starting eleven, you know, we'll be able to extend those numbers out to 16, 17, 18 players and that always makes a difference. We know we're going to have to use our substitutions wisely, and we know that solutions play a huge role in what we do and they have the entire tournament. So we're going to need help from them again tomorrow."
The question of starter versus substitution is not a simple one: If you start players like Lewandowski and Zinckernagel, how confident are you that they'll be able to go the full 90 and make it to PKs should they be necessary? Or do you plan to use your bench early so that the players you're most confident can score goals – and PKs – are on late, when opponents have tired legs?
It's not an easy question, but getting it right may well make the difference between a semifinal berth and the end of a tournament.
