Will Milan Win in the Windy City vs Real Madrid?

After a surprising 3-2 friendly win over Manchester City in New York on Saturday, Milan head to Chicago, also known as the Windy City, to face Real Madrid. Milan also launched their new white away kit while in New York, midmatch, actually, along with Manchester City and Puma, part of an initiative called "City and Milan for Change." That was not the only change in that game, as fans saw more signs of the team's metamorphosis into Fonseca's new style of play. Fans are excited about the win and so many passes, but we cannot forget that we lost Sportiello to a freak hand injury even before the match, and Florenzi is facing arthroscopic surgery on his knee for an injury during the match. There have been some roster changes, too, but the question remains: will Milan win in the Windy City vs. Real Madrid?

Will the arrival of the new players help Milan to victory? Or at least no injuries?

In A New York Minute...

Saturday's match had positives and negatives. During the opening minutes of the match, they looked nervous and stressed, like tiny little dogs, passing the ball as if they had been spooked or something. They started to string a few plays together, but it was Manchester City who scored the opening goal, Haaland, of course, with an assist from his fellow Norwegian, Bobb. 1-0 Man City. They continued to threaten, but it was Chukwueze and Colombo who scored next, Colombo's header too much for Ederson in the 30th. 1-1 all. They repeated virtually the same play, with Chukwueze providing the same cross, but in the 34th, Colombo slotted it home instead. 2-1 Milan. Both Bobb and Haaland continued to threaten as well, and while Milan looked to be more in control, they were still allowing plenty of opportunities.

Obviously, he was going to be too much to handle for Milan's defense.

Florenzi's injury occured five minutes before halftime, and we could all see that he knew it was serious. The MRI shows damage to his meniscus and ACL, but not a full tear, apparently, so he will fly home to Italy sometime soon for his surgery. Hopefully his recovery time will not be as long as a full ACL surgery. Heartbreaking all the way around, because Milan have also stepped up their bids for Emerson Royal from Tottenham as a result, so twice as devastating. Sportiello's injury is being called a "freak accident" and occurred at the hotel, hours before the match. He had to have surgery in the U.S. to repair it, as he had completely severed a tendon in his second finger, and now will return to Italy to begin his recovery process. Milan are also looking to sign another goalkeeper, as he will be out at least two months. Not the best start for Fonseca's injury reduction campaign, even if neither injury was his fault by any means.

The second half, Guardiola made four subs, including taking Haaland off, and whatever he told them, it worked. Milan were pinned back and Man City dominated, with McAtee scoring the equalizer just ten minutes in. 2-2 all. Fonseca made five subs, including changing his center backs, and bringing on three young players: Liberali, Jiménez, and Nasti. Nasti in particular created a number of opportunities as Milan found their way back into the match, and in the 78th, he scored the winner with an assist from Saelemaeker. 3-2 Milan. Pulisic and Musah received huge roars from the U.S. crowd as they and Bakoune all got ten minutes. Fun fact: Musah's U.S. citizenship comes from the fact that he was born in the Bronx, not far from Yankee Stadium, even if he was raised in Italy.

Get well soon, Ale!

Many were impressed with Saelemaekers. He was the player we saw at his best before leaving Milan, but I think he may be forgotten when Leão returns. Although Fonseca was asked about him and mentioned that he was versatile and hardworking and may stay at Milan this season. Chukwueze was the player we all wanted to see last season, he really stood out, particularly with so many starters still missing. But also, he seems revitalized by the faith Fonseca is showing in him. Speaking of Fonseca, this was his second time defeating Pep Guardiola and Manchester City, although this time, he unfortunately did not wear the Zorro costume in the press conference

It should be noted that Liberali got 25 minutes when some players didn't play at all, and he is only 17 years old. A small 17 years old. He is definitely one to watch. And obviously, Colombo, who was excellent for his 65 minutes, with the brace, but also many great opportunities. However, Fonseca indicated afterward that there was depth in the squad, and that he need to play. So he has returned to Italy and his loan to Empoli is currently being finalized, unfortunately.

Two different goalscorers, two different kits, but there is only one Saelemaekers.

After the match, Ibrahimović used his Viking cred to make sure that Haaland knew he was welcome at Milan anytime. He also made up with his previous mortal enemy from his Barcelona days, Pep Guardiola, and they hugged and shared a moment. Grealish photobombed Rihanna's pic with Pulisic and Musah. Leão returned from his vacation. Fonseca and his team looked so happy to have a player to speak Portuguese with. The guys have had a chance to have a bit of fun as they trained, too, including a slam dunk contest and weighing in on their Olympic dreams, as well as the usual promotional photo shoots, etc.

Players also attended the House of Milan event to launch the new away kit on Sunday in New York. The new kit includes a bit of a tribute to Milan's origins as Milan Football and Cricket Club, and you'll notice the cricket props in all the photo shoots as well. The kits worn in the second half of Saturday's match will be auctioned off for charity, including the local Success Academy Charter School, which Fondazione Milan has supported for many years.

The new away kit in New York.

Reunion in Chicago

Last summer, Milan faced Real Madrid in the U.S. as well, it was our first fixture of our summer tour, and it was in front of 100,000 people at the Rose Bowl in Pasadena, California. That was a reunion with our legendary Carletto, but also with our little Brahim, who had only just returned to Real Madrid after his loan spell at Milan. This year, he will greet us as a Champions League winner, as Real are the reigning Champions League title holders... for the 15th time. 

With PDA like that, you know he has moved on.

For Real Madrid, this will be their first stop on their U.S. tour this year, as they only just departed for America on Sunday. Ancelotti is also still waiting on the return of several of his players from international duty, but welcomed the young new addition Endrick to his squad just ahead of this trip, who could debut vs. Milan. Ancelotti named 26 players to his roster for the U.S. tour, with four players set to join them along the way, so they will likely not be available for our match.

Despite having just played Saturday, Fonseca's squad has changed quite a bit. Joining the team since then are Rafa Leão, Okafor, Zeroli, and Camarda. Meanwhile, Sportiello and Florenzi are obviously injured, and Adli also reportedly has a physical problem. Daniel Maldini and Colombo have both returned to Italy, with Daniel Maldini's permanent transfer to Monza just announced and Colombo's loan to Empoli imminent. Reports are that the wounded will stay behind on the East Coast, but also that Okafor also may not travel with the team, having just joined the team in the past few days. The team trained in New Jersey on Tuesday and is flying in ahead of the match, and presumably will return East shortly, as their last match is in Baltimore, Maryland.

The final match of the final Maldini player at Milan... what a tragedy.

Most friendlies are a chance to see the players in an actual game situation, try new tactics and lineups, and generally are glorified training matches. After Saturday's match, fans undoubtedly have raised their expectations and will want to see more progress in adopting Fonseca's identity on the pitch. However, it is already necessary to return to our previous ways... just hoping and praying that no one else gets injured. with two players already out with longterm injuries, we just need everyone to be healthy at the final whistle, no matter what the performance looks like or what the result is.

Is Fonseca's identity on the pitch going to be "Pass it to Rafa?"

That said, this match is sold out, 60,000 tickets sold for Soldier Field, which is not a baseball field, and is actually 100 years old this year. It is usually fun to play Real Madrid, even if the crowd is usually 90% or more Real fans. Hopefully, with more Italian-Americans living in the Chicago area than Southern California, like last year's match, there will be more Milan or Serie A fans this time. But with Real Madrid still dominating Champions League, who are we kidding? It will be a sea of white. However, those who are wearing the red and black will more than likely be concerned about our players' health and welfare than the question of "Will Milan win in the Windy City vs. Real Madrid?"


This post inspired by the music of Frank Sinatra's "Chicago"


Our next match is a Friendly
AC Milan vs. Real Madrid
Wednesday, July 31, 2024 • 7:30pm CDT/8:30pm EDT (02:30 CEST Thurs. 1 Aug.)
Soldier Field, Chicago, Illinois
Watch on ESPN or stream on ESPN+ in the U.S.

Will Milan Win in the Windy City vs Real Madrid? Will Milan Win in the Windy City vs Real Madrid? Reviewed by Elaine on 3:00 AM Rating: 5
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