Los Blancos will be looking to replicate their stellar 2023-24 campaign this time around, whilst the Rossoneri will aim to return to the summit of Serie A this term.
Match preview
Wednesday night's match against AC Milan in Chicago will be Real Madrid's first high-profile contest since they lifted the Champions League at the expense of Borussia Dortmund in London on May 1, when Los Blancos claimed possession of the European crown for the 15th time in their history.
Following a nervy first half in which the Germans could have taken the advantage, Carlo Ancelotti sprinkled his managerial magic once again and the Spaniards raced to victory, with Dani Carvajal and Brazilian superstar Vinicius Jr getting onto the scoresheet at Wembley Stadium.
Real Madrid were also successful on the domestic scene during the 2023-24 campaign, lifting the La Liga title ahead of arch rivals Barcelona and surprise package Girona, with Los Blancos ending up 10 points clear of Xavi's men, who had to settle for second place in the division.
Keen to avoid resting on their laurels ahead of the new season, Ancelotti's side pulled off the standout deal of the summer window to date, with France's Kylian Mbappe moving from Paris Saint-Germain to the Bernabeu at the expiration of his contract at Parc des Princes, ending a transfer saga that had been brewing for half a decade.
Los Blancos have played one game so far in their pre-season schedule, beating fellow Spaniards Albacete 3-0 in Madrid, with assignments against Barcelona and Chelsea to come before the start of Madrid's competitive action on August 14, when they will face Atalanta BC in the UEFA Super Cup.
After a successful two-year stint at French club Lille in Ligue 1, Paulo Fonseca is back in Italy for his next managerial role, taking the reins at AC Milan ahead of a 2024-25 campaign that supporters of the Rossoneri are hoping will end with their 20th top-flight title, beating the likes of Inter Milan to top spot.
The Rossoneri's city rivals ran away with proceedings at the summit of the Serie A standings during the 2023-24 term, finishing 19 points ahead of the chasing pack in the first division, with Stefano Pioli's ending up in second ahead of Juventus, Atalanta and Bologna in the remaining Champions League places.
AC Milan have already been relatively busy in their pre-season plans, losing 5-2 to Roma before sharing the honours with Austrian side Rapid Vienna on July 20, when Alessandro Florenzi's strike was cancelled out by an 88th-minute equaliser from Furkan Demir.
Although warm-up results often fail to predict the fortunes of sides in the upcoming competitive action, Fonseca will be delighted that his troops were able to secure a 3-2 win over Premier League champions Manchester City last time out, with 22-year-old Lorenzo Colombo netting a brilliant brace.
The young striker could provide backup to new arrival Alvaro Morata, who has swapped Atletico Madrid for Milan during the off-season, with the former Chelsea striker coming into this club campaign fresh from Euro 2024 glory.
Real Madrid friendly form:
AC Milan friendly form:
Team News
Real Madrid have announced their travelling squad for the United States tour, with a number of star players set to join up with the team at a later date.
Eder Militao has spent the majority of the summer so far in the United States as part of Brazil's Copa America squad, who were unable to make it to the latter stages under the tutelage of Dorival Junior.
The centre-back's compatriots Vinicius Jr and Rodrygo will also travel out late to the tour, meaning that they will not feature on Wednesday night.
Endrick flew out to North America with the rest of his teammates and could be in line for his Los Blancos debut on Wednesday night in Chicago.
As well as marksman Morata, AC Milan have secured the services of Alex Jimenez this summer for £4.3m, and the 20-year-old could make his debut against his former employers in this one.
Providing two assists during the five-goal thriller with Man City, Samuel Chukwueze is expected to start on the right wing for the Rossoneri.
Real Madrid possible starting lineup:
Courtois; Vazquez, Vallejo, Rudiger, Garcia; Ceballos, Paz, Guler; Diaz, Endrick, Latasa
AC Milan possible starting lineup:
Torriani; Calabria, Tomori, Gabbia, Terracciano; Pobega, Bennacer; Chukwueze, Loftus-Cheek, Saelemaekers; Colombo
We say: Real Madrid 1-2 AC Milan
Although most of the supporters will be cheering on Real Madrid at Soldier Field, we believe that AC Milan should have the advantage in the contest considering that they are further into their respective pre-season schedule.