While most eyes are on the lineup choices of manager Sergio Conceicao, one particular question looms ahead of Saturday's clash: what role will Christian Pulisic play in a Milan team still searching for consistency?

If Pep Guardiola does walk away from Manchester City, where would he go next? Surprisingly, Milan has emerged as a possible destination.

Milan’s season has been filled with inconsistency, but one statistic stands out as particularly alarming: the worst penalty-kick record in Europe’s top five leagues. And at the center of this conversation is Christian Pulisic.

The Derby della Madonnina is always a special occasion, but this Coppa Italia semifinal has added significance. Both AC Milan and Inter Milan are desperate to win a trophy this season, and this match represents a major opportunity to advance to the final.

Santiago Gimenez’s penalty miss against Napoli proved decisive, leaving fans and pundits alike questioning: Why did Milan allow a struggling striker to take such an important kick when Christian Pulisic was on the pitch?

In AC Milan's 2-1 defeat to Napoli in the 2024–25 Serie A season, fans raised eyebrows after designated penalty taker Christian Pulisic handed the spot-kick to Santiago Gimenez, who ultimately missed the chance.

The latest and most harsh assessment has now arrived from a club legend, who insists that only two players have lived up to expectations. But who are the two players who have earned praise?

Video of Santiago Gimenez hobbling into the locker room caused concern among the Milan supporters, even as Mexico's national team celebrated a historic 2-1 win over Panama in the CONCACAF Nations League final.

While the March international break puts a temporary halt to club play, Milan has once again become a household name throughout the world. A staggering 15 Rossoneri players have been called up, making it the most represented Serie A club during this window.

It has been a season of highs and lows for Milan, but one thing remains constant—the club’s fans continue to fill San Siro in record numbers. While on the pitch, the Rossoneri struggle to secure a Champions League spot, off the field, they lead all of Serie A in attendance.

It’s safe to say that fans are both excited and divided about the leaked image of what may be Milan's home jersey for the next 2025-26 season. Based on the recent reports, the design is already being compared to the club’s 2020-21 shirt, which was memorably worn by Zlatan Ibrahimovic in his second stint at San Siro.

Milan’s 2025-26 home shirt, which will be worn by stars like Christian Pulisic, Rafael Leao, and Santiago Gimenez next season, reportedly introduces a new feature never before seen in the club’s history.

Amidst the defensive struggles, head coach Sergio Conceicao is planning a tactical overhaul—one that could redefine Milan’s playing style. While the tactical switch aims to maximize Rafael Leao and Santiago Gimenez’s impact, it also raises questions about the roles of Christian Pulisic and Joao Felix.

Christian Pulisic emerged as the hero for Miian, scoring a decisive brace, while Rafael Leao’s introduction at halftime injected the attacking spark needed to overturn a two-goal deficit.

With Milan struggling, questions have been raised about Santiago Gimenez’s recent dip in form. Is he still recovering from an injury? Has he struggled with the transition to Italian soccer?