Christian Pulisic on edge as Milan braces for crucial Derby della Madonnina battle: Will Santiago Gimenez recover in time for Serie A clash vs. Inter?

As the Derby della Madonnina approaches, the question overshadowing Milan’s preparation is simple yet charged with suspense: Will Santiago Gimenez recover in time?

Christian Pulisic enters this week as both symbol and engine of Milan’s resurgence, while Santiago Gimenez lingers in the shadows of a storyline filled with uncertainty. As the Derby della Madonnina approaches, the question overshadowing Milan’s preparation is simple yet charged with suspense: Will Santiago Gimenez recover in time? That mystery, paired with Pulisic’s explosive form, gives Sunday’s clash with Inter a tension that goes far beyond the table.

The American has travelled a long road to become Milan’s creative heartbeat. From the twitchy prodigy at Dortmund to the inconsistent forward at Chelsea, the promise was always there. It simply needed the right tactical soil, and the Rossoneri provided it.

Since arriving in the summer of 2023, the USMNT star has grown from a hopeful reclamation project into one of Serie A’s most productive attackers. His first season ended with 15 goals and 10 assists across all competitions, followed by an even sharper 17-goal, 10-assist return in 2024-25. What changed? Everything in the margins: smarter pressing, cleaner third-man runs, improved chemistry with Rafael Leao, and a final touch that finally matches his ambition.

The early months of 2025-26 have reaffirmed that transformation. The 27-year-old opened the campaign with a blistering run, scoring in the Coppa Italia and producing a brace-and-assist performance that signaled the Rossoneri’s intentions. Through mid-November, he already has four Serie A goals and two assists, ranking among the league’s most dangerous forwards.

Those numbers are not statistical noise; they are the foundation of Milan’s title push heading into a derby that could shift the balance of power in the city. Thus, this weekend’s meeting of Milan and Inter is arguably the biggest Serie A fixture of the season. The Nerazzurri lead the league by the narrowest of margins, while Milan sits within touching distance thanks to Pulisic’s consistency and the side’s early-season resilience.

The Gimenez question finally revealed

Until now, one issue has hovered in the background of Milan’s preparations: Santiago Gimenez’s condition. Reports across Italy painted a picture of a striker pushing desperately to make it back in time.

However, according to Sky Italia and La Gazzetta dello Sport, “Gimenez was again not in full training on Friday” and remains limited by the ankle problem that kept him out of Mexico’s recent international fixtures. Gazzetta adds that “it’s unlikely he’ll even make the bench,” confirming that the striker is almost certainly ruled out.

This absence carries weight not only because of Gimenez’s finishing but because of how he enables Pulisic and Leao. Without his hold-up play, the dynamic pair must operate in roles neither fully prefers. Yet manager Massimiliano Allegri will not rush a return. As Gazzetta dello Sport reports: “For him to return, it has to be a full recovery.”