The first big chance fell the way of Udinese, when Isaac Success sent Jordan Zemura on his way down the wing and, while his cut-back could not initially find a teammate, Alessandro Florenzi diverted the ball straight to Roberto Pereyra, who fired over from close range. Milan’s first real chance, meanwhile, came in the form of a near-post header from Rade Krunic, which flew wide following Tijjani Reijnders’ corner.
Both sides created half-chances midway through the half; Zemura continued to be a livewire and his cross was headed over by Success, before visiting goalkeeper Marco Silvestri was tested from distance by Davide Calabria.
Milan began to take control after the 30-minute mark, with wingers Rafael Leao and Yunus Musah trying their luck, before Leão found Florenzi free in the box, he executed an astounding Dennis Bergkamp-esque turn, but failed to connect with the shot.
Early in the second half, Christian Kabasele could not keep his effort down after a corner was flicked on to the back post, before half-time substitute Noah Okafor played in Reijnders, whose deft chip trickled wide after evading Silvestri. The match's big moment, however, occurred on the hour-mark, when Festy Ebosele went to ground inside the Milan box.
Referee Juan Luca Sacchi adjudged Yacine Adli to have brought the right-back down and awarded a penalty after a VAR check and, from the spot, Roberto Pereyra kept his cool, sending Mike Maignan the wrong way for his first of the season. Le Zebrette came close to doubling their advantage when Success’ header tested Maignan from a well-worked corner.
Milan threw bodies forward in search of an equaliser late on, with Leão often the orchestrator, but Udinese held firm. As the clock struck 90 minutes, Olivier Giroud diverted the ball goalwards with his shoulder, only for Silvestri to claw it away.
Defeat for Milan heaps further pressure on Stefano Pioli as the Rossoneri lost further ground to city rivals Inter. Meanwhile, three vital points at the San Siro means Udinese have now put breathing space between themselves and the relegation zone, as they move onto five points from three matches in the Cioffi era.
Flashscore Man of the Match: Jordan Zemura (Udinese)