AC Milan will be reunited with one of its legendary figures on Wednesday when it begins its tour of the United States with a meeting with Bayern Munich and the German giant's new coach Carlo Ancelotti. The Italian was a part of four of Milan's seven European Cup triumphs, two as a player and two as a coach.

Since leaving the San Siro in 2009, he has continued to work and enjoy success at some of Europe's top clubs, notably becoming just the second manager ever to win three European Cups when guiding Real Madrid to the title two years ago. As he prepares for his first season at his latest glamorous stop, he will now come face-to-face with Milan at Chicago's Soldier Field as both teams commence their participation in the annual exhibition event the International Champions Cup.

While for Bayern this season, after four successive Bundesliga titles but three straight Champions League semifinal defeats, the aim is the Champions League title, Milan's ambitions are now far more modest. Since Ancelotti's exit, Milan has been on a gradual downward trend and now face a third straight season without any European action, the first time that has happened in 30 years. Ancelotti was happy to elaborate on what he think has changed since his time in charge.

“Of course I'm going to meet some people that have worked with me in Milan that are still working in Milan,” he said at a press conference at Soldier Field on Tuesday. “I have a really good memory of that moment, of the people. When you are not there, it's not easy to explain what happened. Milan changes its politics. For many years I think [owner, Silvio] Berlusconi spent a lot of money to keep the team at the top in Europe and now I think he's a little bit tired of that and he tried to use another way.”

Indeed, Milan will be beginning its preseason with the future ownership of the club still uncertain. Berlusconi is again said to be in advanced negotiations to sell, but no deal has yet been finalized. Meanwhile, it will commence the campaign with a new manager for the third successive season.

After both Sinisa Mihajlovic and Cristian Brocchi came and went last season, which ended with Milan finishing seventh in Serie A, Vicenzo Montella is the latest man to try and help revitalize the team. The former Italy striker spent some time with Ancelotti at Chelsea five years ago before beginning his coaching career at Roma and subsequently moving onto Catania, Fiorentina and Sampdoria.

“I worked with him while I was at chelsea so I have great feelings toward him,” Ancelotti said of his opponent on Wednesday.

Bayern Munich will be without a host of first-team players in Chicago due to their participation in Euro 2016, including new signings Mats Hummels and Renato Sanches, as well as the likes of Thomas Muller and Manuel Neuer. There will still be ample quality at Ancelotti's disposal, including Philipp Lahm and Arturo Vidal, as well as the fit again Holger Badstuber.

Milan will be without last season's top scorer Carlos Bacca, as well as new signing Gianluca Lapadula. Still, Montella, who guided Milan to a 1-0 victory over Bordeaux in his first match in charge, is eager for his new team to play on the front foot.

“Compared to the match against Bordeaux we have 10 more days of work, but in every game you have to take a step more,” he said. “We have to have the same desire to want to control the match, even if tomorrow will be difficult but you have to try and take the game forward.”

Kickoff Time: 9 p.m. EDT

TV Channel: ESPN2, ESPN Deportes

Live Stream: Watch ESPN

Tickets: Ticketmaster