Carlo Ancelotti’s preparations for his first season in charge with Bayern Munich will continue on Wednesday with a contest against one of his former clubs, AC Milan, at Chicago’s Soldier Field. The Italian’s career has taken him to several of Europe’s biggest clubs, most recently Real Madrid, who Bayern will face to complete its three-match tour of the United States for the International Champions Cup.

He has won silverware with every one of his employers since leaving Parma for Juventus 18 years ago. His specialty, though, has been in the Champions League, most notably with Milan. Indeed, his happy relationship with the competition dates back to his time as a player when he was a part of the Milan team that was the last to lift the trophy in back-to-back seasons, in 1989 and 1990.

Upon returning to the club as a manager in 2001, Ancelotti then lifted the European Cup twice more, in 2003 and 2007. Having also won the competition with Real Madrid two years ago, becoming just the second coach in history to win it three times, it is clear what the expectation will be of him at Bayern.

In Pep Guardiola, Ancelotti has replaced a coach who helped perfect an eye-pleasing possession style and dominated domestically, winning three Bundesliga titles and two German Cups. But he couldn’t get the team over the line in the Champions League, losing in the semifinals in each of his three seasons in Bavaria.

As he seeks to improve on that record, Ancelotti’s squad has been boosted by the arrival of World Cup winner Mats Hummels from Borussia Dortmund and young Portuguese sensation Renato Sanches. Neither, though, will be in the United States, as they enjoy their extended layoff following Euro 2016. To his doubtless frustration, Ancelotti will also have to do without the rest of the Germany contingent – Manuel Neuer, Jerome Boateng, Thomas Muller and Joshua Kimmich – as well as Poland’s Robert Lewandowski and France’s Kingsley Coman until the German Super Cup against Dortmund on Aug. 14. Meanwhile, Arjen Robben and Douglas Costa have not made the trip to the U.S. due to injury.

And yet still there will be plenty of quality on show at Soldier Field, with Arturo Vidal, Philipp Lahm and David Alaba among those in the touring party. They are riches that Milan can now only dream of.

It would be no surprise were Ancelotti’s presence in the opposing dugout on Wednesday not to bring a painful realization for Milan supporters of just how far the club has fallen since the heights of winning the Champions League twice in four years. Indeed this season Milan will embark on its third successive season without European action of any kind, the first time that has happened in more than 30 years.

While there are clearly much wider problems at the club, Milan continues to run through managers and is now on its eighth since Ancelotti departed in 2009. Vincenzo Montella is now the man in the hot seat, yet he continues to be hampered by uncertainty over the club’s ownership with Silvio Berlusconi’s long discussed plans to sell the club yet to be finalized.

It means so far Montella has been restricted to signing just one player for a fee, striker Gianluca Lapadula, who scored 30 goals in Serie B for Pescara last season. Meanwhile, the club’s top scorer last campaign, Carlos Bacca, continues to be linked with a move away from the San Siro. The Colombia, along with Lapadula and defender Mattia de Sciglio, has not traveled to the U.S., although the club insists that is as a result of injury rather than an impending transfer.

AC Milan Squad vs. Bayern Munich

Gianluigi Donnarumma, Diego Lopez, Gabriel, Alessandro Livieri

Defenders:  Ignazio Abate, Luca Antonelli, Davide Calabria, Ivan de Santis, Rodrigo Ely, Gabriel Paletta, Alessio Romagnoli, Jherson Vergara

Midfielders: Andrea Bertolacci, Giacomo Bonaventura, Keisuke Honda, Juraj Kucka, Riccardo Montolivo, Andrea Poli, Mattia El Hilali, Niccolo Zanellato

Forwards: Luiz Adriano, Alessandro Matri, Jeremy Menez, Mbaye Niang, Suso, Luca Vido

Bayern Munich Squad

Christian Fruchtl, Tom Starke, Sven Ulreich

Defenders: David Alaba, Holger Badstuber, Juan Bernat, Nicolas Feldhahn, Tim Hausler, Philipp Lahm, Rafinha

Midfielders: Xabi Alonso, Fabian Benko, Niklas Dorsch, Javi Martinez, Erdal Ozturk, Franck Ribery, Thiago, Timothy Tillman, Arturo Vidal

Forwards: Mario Crnicki, Julian Green, Karl-Heinz Lappe, Milos Pantovic

Match Details

Soldier Field, Chicago

Time: 9 p.m. EDT