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Milan’s Serie A rotation dilemma vs. Bologna: Who will Conceicao trust between Rafael Leao, Christian Pulisic, Santiago Gimenez, and Joao Felix?

Christian Pulisic, Rafael Leao (left), Sergio Conceicao (center) and Joao Felix (right)
© Getty ImagesChristian Pulisic, Rafael Leao (left), Sergio Conceicao (center) and Joao Felix (right)

Milan boss Sergio Conceicao is widely expected to rotate his squad for the upcoming Serie A match against Bologna. With just three league games remaining and the Coppa Italia final looming, the Rossoneri are walking a delicate tightrope. The question now is: Who among Rafael Leao, Christian Pulisic, Santiago Gimenez, and Joao Felix will take the field at San Siro?

This has not been the season Milan envisioned. After entering the campaign with high expectations, the club now finds itself on the outside looking in at Europe’s premier competitions. Both Champions League and Europa League qualification seem just out of reach—six points adrift from each, while even a UEFA Conference League spot is five points away.

Yet, a late-season twist remains possible. The Rossoneri’s fate may partially rest in the hands of others, especially with Lazio and Juventus facing off this weekend, potentially allowing both to drop crucial points. But to take advantage, Milan must win every remaining game—starting with Bologna, then Roma, and Monza.

Failing to deliver on this front would mean falling back on the Coppa Italia final, scheduled for May 14, as a final chance at both silverware and European qualification. With the pressure mounting, Conceicao is expected to rotate his squad on Friday night to keep key players fresh for that decisive showdown.

Who’s in and who’s out?

Rafael Leao is confirmed to miss the Bologna match due to suspension, ruling out one of Milan’s most explosive forwards. His absence alone forces a change in the attacking setup. Meanwhile, Christian Pulisic is expected to be rested, having been overextended in recent matches. According to Tuttosport, “Pulisic seems in need of some rest… Joao Felix and Samuel Chukwueze could play behind the striker.”

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That striker? Santiago Gimenez, who is tipped to start, has been steadily regaining form after a rocky introduction to Serie A. The Mexican striker made a strong impression off the bench in Milan’s recent wins over Venezia and Genoa, scoring and assisting in crucial moments. The Mexican star may be the team’s X-factor as the season closes. Despite early doubts, he has shown in recent weeks that his adaptation to Italian soccer is well underway.

Santi Gimenez

After battling through injury and a goal drought, the 23-year-old is now playing with purpose and clarity. His ability to stretch defenses and create space has added a new dimension to the San Siro outfit’s attack. And with the final on May 14 looming, he knows this is his chance to silence critics and etch his name into club folklore.

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Joao Felix, who has developed a strong connection with Gimenez, provided the pass that led to Rafael Leao’s equalizer in the Genoa game. His creativity and movement will be crucial in Pulisic and Leao’s absence.

Joao Felix Milan

Changes expected in defense

In addition to the attacking reshuffle, defensive rotation is also expectedKyle Walker will return to the starting lineup, giving Conceicao the flexibility to rest either Fikayo Tomori or Alex JimenezMalick Thiaw is also set to start, adding fresh legs and physicality to the back three.

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These adjustments aren’t merely tactical—they’re protective. With the Coppa Italia final just days away, any additional injuries could be catastrophic for a team already short on depth and momentum.

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