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AC Milan will face city rivals Inter at San Siro for the first leg of the Coppa Italia semifinals, as the two sides meet again after the two Serie A derbies and the Supercoppa Italian final when Sergio Conceicao's side managed to make a comeback in the second half and won the first trophy of the season. While the Rossoneri are still unbeaten this season against Simone Inzaghi's team, things are now much different between the two teams as Inter are currently leading the Serie A standings with a three-point margin on Napoli and are also due to meet Bayern Munich next week for the first leg of the UEFA Champions League quarterfinals. 

The Rossoneri are struggling a lot this season and despite winning the Suercoppa Italiana against the same Inter, the Italian giants were not able to overturn a disappointing season even after a managerial change. Conceicao replaced former Portuguese coach Paulo Fonseca at the end of the December, but after winning the Supercoppa, the former FC Porto head coach didn't deliver the results hoped before the start of the season and especially after the January transfer moves, as AC Milan decided to replace players like Spanish striker Alvaro Morata and signed Mexican forward Santiago Gimenez, Chelsea loanee Joao Felix and former Manchester City captain Kyle Walker. 

While the season is coming to an end and AC Milan are currently in ninth place in the Serie A standings, the Coppa Italia becomes their biggest chance to qualify for the Europa League while Inter are dreaming of a treble, as they are still in the race in all the competitions. The two Derby della Madonnina that will take place in the coming weeks will define the future of both sides ahead of the last month of action. Here are storylines, how you can watch the match and more:

How to watch AC Milan vs. Inter, odds

  • Date: Wednesday, April 2 | Time: 3 p.m. ET
  • Location: San Siro -- Milan, Italy
  • Live stream: Paramount+
  • Odds: AC Milan +225; Draw +245; Inter +115

Last meeting

The two sides met three times already this season, two in the Italian Serie A and one in the Supercoppa Italiana final in January. AC Milan won the first two, one each under Fonseca and Conceicao, and the second one the Rossoneri were down 2-0 before making an incredible comeback in the last minutes of the final, winning 3-2 at the stoppage time thanks to the late winner of former AS Roma striker Tammy Abraham. The two teams met again one month later, when they drew 1-1 thanks to the last minute equalizer of Stefan de Vrij. 

Lineup questions

Inter are struggling with injuries, as club captain Martinez is also expected to miss Wednesday's tie. Inzaghi also spoke about him in the press conference ahead of the Derby della Madonnina.

"I hope to have him available on Saturday in Parma, but we have to see day by day. You make tables in your head, then setbacks can come. He's fine, he's working. If it were up to him, we all know he always wants to be there, but unfortunately, he had the problem with Atalanta."

Conceicao, on the other hand, is dealing with some other issues as midfielder Ruben Loftus-Cheek underwent successful surgery for acute appendicitis on Sunday, a few hours before the Napoli game, when he was supposed to start against Antonio Conte's side. Rafael Leao started from the bench against the Azzurri and it created a lot of criticism around the Portuguese coach, which justified the decision due to a minor injury. Leao is expected to start on Wednesday against Inter. 

What the coaches are saying

Conceicao spoke about the difficult moment of the team ahead of the last stint of the season and after losing 2-1 against Napoli over the weekend.

"I have nothing to do with these wars. I speak as a coach. I am focused on winning titles. I have won some, 13, so that's it. I am in this situation, in ninth place, when in Portugal with teams that I was fighting not to be relegated, I was higher. I am a coach who fights every match to win and reach important goals, not for ninth place. We can see the glass half full and empty. If we have to talk, see how many years Milan haven't won two titles. Of course, in terms of the standings, it's critical. At this moment, it's not Milan. [Wednesday's] match is important because it allows us to get closer to a final, to a title."

Inter manager Simone Inzaghi underlined the issues regarding the injuries of the roster.

"We didn't need the setback that [Mehdi] Taremi had, playing his second match with his national team. Without Lautaro [Martinez on Wednesday], we will have to play with three forwards ... We know that it will be a challenge to be played over 180 minutes; it is not a league game and there will be the return at the end of April. However, there is always the desire for a great approach like in the last games," he said. 

Predicted lineups

AC Milan: Mike Maignan; Kyle Walker, Malick Thiaw, Matteo Gabbia, Theo Hernandez; Yunus Musah, Youssouf Fofana; Christian Pulisic, Tijjani Reijnders, Rafael Leao; Santiago Gimenez.

Inter: Josep Martinez; Benjamin Pavard, Francesco Acerbi, Alessandro Bastoni; Matteo Darmian, Nicolo Barella, Hakan Calhanoglu, Davide Frattesi, Federico Dimarco; Joaquin Correa, Marcus Thuram.

Player to watch

Davide Frattesi, Inter -- The Italian midfielder was close to leaving the Nerazzurri in the January transfer window after the same player showed his disappointment for the little game time he had in the first part of the season. Despite his agent trying to find another club as AS Roma showed interest, Frattesi didn't leave Inter in January, and he's now finally playing more, also thanks to the injury of Piotr Zielinski, who will be unavailable for another month. The former Sassuolo midfielder scored the second goal of the weekend as Inter won 2-1 against Udinese on Sunday, and he's expected to start again against the Rossoneri in the first leg of the semifinals. 

Storyline to watch

AC Milan close to appointing a new director -- The Italian club is finally getting closer to appointing the new sporting director, a key figure that will decide the manager position in the summer and also will work closely with both CEO Giorgio Furlani and RedBird advisor Zlatan Ibrahimovic. The club seemed a bit lost after not replacing club icon Paolo Maldini and sporting director Ricky Massara in the summer of 2023, and for this reason, they are now looking to find a new figure that will lead the sporting side of the team over the next years. AC Milan are now close to appointing former Juventus and Tottenham man Fabio Paratici, according to multiple reports. 

Prediction

It will be a tense semifinal as both AC Milan and Inter need to avoid a defeat. Both teams also know that there will be a second leg in less than three weeks and that can have an influence on Wednesday's clash. Pick: AC Milan 1, Inter 1. 

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