AC Milan’s quest for silverware begins this Friday as they face Juventus in the semifinals of the 2025 Italian Super Cup. With the tournament offering a lucrative prize pool, Milan’s key players, Christian Pulisic and Rafael Leao, stand to gain significantly—both financially and in terms of legacy—should the team go all the way.
It has been a challenging few years for the Rossoneri, with the club striving to rediscover its winning ways. Their last major triumph came in 2022 when they clinched the Serie A title. Now, under new coach Sergio Conceicao, the Rossoneri hope to end their trophy drought in the Supercoppa Italiana.
This year’s Supercoppa Italiana follows a four-team mini-tournament format rather than the traditional one-off match. The participants include:
Milan will first face Juventus, and if successful, will meet the winner of the other semi-final between Inter and Atalanta in the final. The Rossoneri’s ultimate goal? To win their first Supercoppa since 2016 and secure €8 million in prize money, not to mention the prestige of lifting the trophy.
The tournament boasts a lucrative €23 million prize pool, divided as follows:
| Stage | Prize Money (€) |
| Semi-final participation | €1.6 million |
| Semi-final winners | €3.6 million |
| Finalist (runner-up) | €5 million |
| Winner | €8 million |
Each team is already guaranteed €1.6 million for reaching the semi-finals. A semi-final victory would increase that figure to €3.6 million, while the losing finalist receives an additional €5 million. The champion claims the largest share, walking away with €8 million—a significant boost to any club’s finances.
Milan’s success in the Supercoppa largely hinges on the performances of Christian Pulisic and Rafael Leao, though their participation remains uncertain. Pulisic has been instrumental this season, with eight goals and five assists across all competitions, making him Milan’s top contributor. His return to full training ahead of the semifinal is a welcome boost for the squad. However, concerns linger over whether he will start or be eased in from the bench.
Meanwhile, Leao, recovering from a flexor strain, is unlikely to feature in the starting lineup. There is even doubt over his availability on the bench. His absence could force Conceicao to alter his tactics, potentially shifting to a two-striker formation.
If both players are fit, their presence would significantly enhance Milan’s chances of securing the €8 million top prize and claiming their eighth Supercoppa title, a feat they last achieved in 2016.
