Beneath the surface of Milan’s win against Inter, there’s a quieter, more urgent reality. One that demands more from the Rossoneri’s biggest names—Christian Pulisic, Santiago Gimenez, Rafael Leao, and Joao Felix—and one that insists their season is far from finished, regardless of the Coppa Italia final on May 14.
It should be a time for celebration. Milan has just booked their place in the Coppa Italia final, stunningly defeating fierce rival Inter. The 3-0 win in the second leg at San Siro completed a resounding 4-1 aggregate triumph, a performance that felt like a revival, like the Rossoneri had finally turned the corner.
But beneath the surface of that triumph, there’s a quieter, more urgent reality. One that demands more from the Rossoneri’s biggest names—Christian Pulisic, Santiago Gimenez, Rafael Leao, and Joao Felix—and one that insists their season is far from finished, regardless of the Coppa Italia final on May 14.
Milan will face Bologna at the Stadio Olimpico in Rome in their first Coppa Italia final appearance since 2018. Their opponents, meanwhile, have waited 51 years for a shot at the trophy. It’s a matchup few would have predicted, and one that carries not just historical weight, but financial consequence.
“Just reaching the final guarantees €4.6 million ($5.25 million),” according to Football Italia. “Winning the Coppa Italia would raise that figure to €7.1m ($8.1 million), and another €10m ($11.4 million), could follow by winning the Supercoppa Italiana.”
That’s a potential €17 million ($19.3 million) prize, a welcome windfall with a crucial summer rebuild looming, especially given the club’s uncertain financial position. Add to that the prestige of lifting a trophy and securing a Europa League berth for the 2025-26 campaign, and the stakes are clear. But for all that the Red and Blacks stand to gain in Rome, they could lose just as much if they ignore what’s left in the league.
The hidden cost of a ninth-place finish
The Rossoneri’s domestic campaign has been inconsistent, to say the least. After 14 wins, nine draws, and ten defeats, Milan currently sit ninth in Serie A, adrift of the European places. A run in the Champions League that included a memorable win over Real Madrid ended in heartbreak against Feyenoord. Domestically, it has shown flashes of promise but failed to deliver when it mattered.
Finishing outside the top eight may not seem disastrous—after all, the club is in a cup final—but it carries an often-overlooked penalty. Teams that place ninth or lower must begin their Coppa Italia journey in the third round, scheduled for August. That would mark an unusually early and physically demanding start to the 2025-26 campaign, especially with a new coach likely to be at the helm.
As La Gazzetta dello Sport reports, “it’s likely the first competitive match of the next season will come under a new manager, and starting from the third round adds unnecessary pressure.”
In contrast, clubs finishing in the top eight enter the competition directly at the Round of 16, offering more time for preseason preparation and squad integration. For a club aiming to rebuild and re-establish itself in Europe, that difference could be decisive.
Time for the stars to shine
To avoid that fate, Milan’s biggest stars must step up. The final three league matches—against Venezia, Genoa, and Bologna—could be the difference between an early start and a strategic one next season.
Christian Pulisic has been one of the two rare bright spots this season. Joao Felix, still searching for his first Serie A goal, remains enigmatic. Rafael Leao has the raw ability to change any game, but questions about his consistency persist. Santiago Gimenez, who shone in the quarter-final against Roma, must now assert himself as the reliable finisher Milan have lacked – that is, if he manages to reclaim his place in the starting line-up.
