Sergio Conceicao’s first game in charge of AC Milan was unforgettable, as his team came from 1-0 down to win 2-1 against Juventus in the second semi-final of this season’s Supercoppa Italiana in Riyadh.
Juventus, the only Serie A team still unbeaten in the league this season, were expected to start strongly, especially against a team they hadn’t conceded against in their last three meetings.
Milan kept up with Juventus in the first 20 minutes, but it was Juventus who struck first. Kenan Yildiz scored with a beautiful shot into the top-right corner of Mike Maignan’s net after receiving a pass from Khéphren Thuram inside the box.
Given that five of the last six meetings had fewer than two goals, Milan’s chances of a comeback seemed slim.
The teams continued battling for the rest of the first half, with Yildiz’s goal being the only shot on target.
After the break, Milan switched to a higher press and nearly equalised in the 55th minute. A rebound fell to Theo Hernandez in the box, but he sliced his shot over the bar.
Juventus kept Milan at bay with calm possession, and it wasn’t until the 70th minute that Milan tested Juventus keeper Michele Di Gregorio. Tijjani Reijnders took a long-range shot, but Di Gregorio kept it out, preventing the ball from going into the bottom-left corner.
However, Milan’s chance came soon after. Manuel Locatelli fouled Christian Pulisic inside the box, and Pulisic took the penalty. His shot went straight down the middle with enough power that Di Gregorio could only parry it into the net for 1-1.
From that moment, Milan were full of energy and completed the turnaround five minutes later. Rafael Leao broke down the right, aiming to cross for a teammate, but as goalkeeper Di Gregorio rushed to intercept, Federico Gatti’s leg redirected the ball into the empty net.
The final minutes were tense, but Milan held their nerve to win, setting up a winner-takes-all derby against Inter in the Supercoppa final. They also ended Juventus’ unbeaten run at 14 matches.

A win in the final on Monday would level Milan with Inter on eight cup wins and bring them to within one of Juventus’ record of nine.

