As the only Serie A team yet to taste a league defeat in 2024/25, Juventus were expected to make a strong start, especially against a team they hadn’t conceded against in three H2Hs.
And although Milan initially matched the Old Lady in a true baptism of fire for their new boss in the opening 20 minutes, Juventus drew first blood via Kenan Yildiz, when he latched onto a pass from Khéphren Thuram inside the box and fired exquisitely into the top-right corner of Mike Maignan’s net.
With five of the previous six H2Hs producing less than two goals, history was firmly against Milan mounting a comeback inside 90 minutes.
The two sides resumed their war of attrition for the remainder of the first half, with Yildiz’s strike staying as the only effort on target.
Little changed immediately after the restart either, though Milan’s switch to a higher press nearly paid off on 55 minutes, when a rebound fell to Theo Hernandez inside the box, only for him to slice an effort over the bar.
Juventus kept Milan under wraps with calm possession play, and it wasn’t until the three-quarter mark that the Rossoneri finally tested Michele Di Gregorio, as Tijjani Reijnders let fly from distance with a shot that Juventus’ custodian prevented from flying into the bottom-left corner. It was a fleeting reprieve though, as Manuel Locatelli brought down Christian Pulisic inside the box after a series of passes.
The American himself stepped up to take the penalty, and though he went straight down the middle, the power meant Di Gregorio could only parry it high into the net for 1-1.
Milan were a force reborn from that moment, and completed the turnaround within five minutes. Once more, lady luck was on the Rossoneri’s side, with Rafael Leao breaking down the right flank and trying to centre for a lurking teammate. However, at the same time Di Gregorio was preparing to charge out and intercept, Federico Gatti stuck a leg out, sending the ball spinning into an empty net.
As expected, the closing minutes were packed with tension, but Milan held their nerve to book a winner-takes-all derby against Inter in the Supercoppa final, while also ending Juventus’ impressive unbeaten run at 14 matches.
A victory in the final on Monday evening would see Milan draw level with their city rivals on eight cup wins, while moving to within one of Juventus’ competition-high nine.