Christian Pulisic's Milan bounced in Supercoppa Italiana semis as USMNT star's trophy chances take hit

It was a disappointing day in Riyad for Christian Pulisic and AC Milan as the Rossoneri lost 2-0 in the Supercoppa Italiana semifinal against Napoli and miss their first chance to win a major trophy this season. The team coached by Antonio Conte, on the other hand, will meet the winner of Bologna vs. Inter, which will take place on Friday at 2 p.m. ET. On Monday, the final will be played at 2 p.m. ET at the King Saud University Stadium. 

Thursday's match did not go as planned for Massimiliano Allegri's side, who conceded twice to David Neres and Rasmus Højlund due to defensive errors by the Rossoneri. The game also exposed flaws within the team that had not been evident earlier this season. After losing to Lazio in the round of 16 of the Coppa Italia and the Supercoppa defeat, Pulisic's only chance to win a trophy with AC Milan this season is now on the Serie A title, as the Italian giants are not part of any European tournament due to the disappointing 2024-25 season. 

Allegri decided to bench some of the biggest stars of the team in the semifinal, including former Real Madrid captain Luka Modric, who only entered the pitch in the final minutes, showing that this team needs a player of his talent in the midfield. AC Milan this season have demonstrated to be consistent, but this defeat against Napoli is only the third one of the season, after the Serie A opening game against Cremonese on Aug. 23 and the Coppa loss to Lazio on Dec 4. 

AC Milan should now focus on the league with some more days of rest compared to the competitors, such as Napoli and Inter, as they will now meet Hellas Verona on Dec. 28 before meeting Cagliari, Genoa and Fiorentina, teams that are all competing to avoid relegation. This is going to be a crucial stint for both Pulisic and the Italian giants as the upcoming schedule can give them a boost to their title hopes. The American international, who already scored nine goals and provided two assists in the 14 games he played so far in all competitions during the 2025-26 season, is still hoping to win a major trophy this season ahead of the 2026 World Cup, where he will lead the USMNT at home.

Winning the Serie A title would be an incredible achievement, and the Rossoneri have a genuine chance to make it happen given Massimiliano Allegri's experience and the quality of the squad at his disposal. However, the semifinal loss to Napoli showed that, despite their injuries, Conte's side must still be considered the team to beat as reigning champs.