Two decades later: Can Milan’s firepower of Christian Pulisic, Rafael Leao, Santiago Gimenez, and Joao Felix end the Coppa Italia curse?
After years of heartbreak and near misses, Milan stands on the brink of domestic cup glory, with Christian Pulisic, Rafael Leao, Santiago Gimenez, and Joao Felix all poised to lead the Rossoneri into the Coppa Italia final against Bologna. The May 14 clash at Rome’s Stadio Olimpico offers not just a chance at silverware, but a symbolic end to a long and frustrating wait.
This match will be a one-off final, decided by regulation time, extra time, or penalties if needed. But for Milan, this isn’t just about winning a trophy—it’s about reclaiming part of their legacy.
The Rossoneri’s road to the final has been impressive, capped by a commanding 3-0 second-leg semi-final win over arch rival Inter. That result, following a 1-1 draw in the first leg, gave them a 4-1 aggregate victory and continued their dominance over the Nerazzurri this season. The win wasn’t just a triumph in terms of tactics or talent—it was psychological, a statement of intent.
Luka Jovic led the way in that match with a brace, while Christian Pulisic played a key role, helping to contain Inter’s midfield threat. Tijjani Reijnders added a late goal to seal the deal, but it was the collective commitment and balance that showed a Milan side capable of controlling high-pressure moments.
Historic challenge
Interestingly, it’s been over two decades since Milan last lifted the Coppa Italia—a span stretching back to 2003, when the Rossoneri edged out Roma over two legs. Despite being one of Italy’s most storied clubs, Milan’s domestic cup history has often been underwhelming. The Red and Blacks won the Italian Cup just five times and lost nine finals. Their most recent appearance in the final, in 2018, ended in a humbling 4-0 defeat to Juventus.
Now, with a new generation of talent spearheading the squad, Sergio Conceicao’s side looks poised to change that narrative. The likes of Santiago Gimenez, a relentless forward presence when in form, and Joao Felix, who at times can bring a sense of flair and creativity, add layers to a squad that already includes the pace and unpredictability of Leao and the discipline and versatility of Pulisic.
Resurgent Bologna and what a win would mean for Milan
Their opponent, Bologna, is writing its own Cinderella story. The Rossoblu have not appeared in a Coppa Italia final since 1974, when they defeated Palermo to claim the trophy for the second time in their history. Their return to the final was sealed with a 5-1 aggregate win over Empoli, after a dominant 3-0 first-leg victory and a 2-1 triumph in the return fixture.
The upcoming final will mark the first time Milan and Bologna meet in the Coppa Italia final, and it adds another layer of intrigue: the two sides are also scheduled to clash in Serie A just days before the final, on the weekend of May 10-11. That league encounter could offer a preview—or a psychological edge—for what’s to come in Rome.
For Milan, the stakes extend beyond silverware. Winning the Coppa Italia guarantees automatic qualification to the UEFA Europa League, an important fallback for a team that has struggled with consistency in the league this season. Currently outside the European qualification spots in Serie A, the final represents a critical opportunity to keep Milan on the continental stage.