Patrick Cutrone scored in the last-minute of added time to send the Giallorossi to a sickening loss, after Federico Fazio had earlier cancelled out Franck Kessie's strike.
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The Giallorossi faced a number of chances in the first half but seemed to grow into the contest as it wore on, only to be undone at the death.
The result means the side have four points from their opening three games in Serie A - with the international break now to come.
TEAM NEWS
Coach Eusebio Di Francesco opted for a 3-4-3 formation - with Kostas Manolas, Ivan Marcano and Federico Fazio all starting in defence
With Marcano making his debut, Rick Kardsorp also made his first appearance of the season for the Giallorossi - while Steven Nzonzi started for the first time.
In attack, Edin Dzeko and Patrik Schick were joined by Javier Pastore.
16' - Calabria gets in behind the defence but fires over from 12 yards out.
17' - Olsen does well to dive low to his left to tip away Higuain's attempt at the near post. The corner comes to nothing.
28' - Another good save from Olsen, this time to deny Suso from distance.
35' - A nice move sees Schick meet Kolarov's cross at the near post - the header is on target by Donnarumma is able to save and hold.
40' - Goal. Milan take the lead. Kessie slots home at the far post. 1-0.
49' - Narrowly wide from Edin Dzeko! A decent start to the half!
59' - GOAL! WE'RE LEVEL! FAZIO! What a finish! The ball falls to the defender inside the box, and he rifles home from 15 yards out! 1-1.
62' - VAR. Milan think they are back ahead through Higuain... but after a VAR review the goal is chalked off for offside! Still all-square!
66' - Olsen blocks Calhanoglu's shot, and the attacker cannot hit the target when the rebound comes back to him.
79' - GOAA.... No! This time it's the hosts' turn to benefit from VAR - Nzonzi prods the ball home from a corner, but the referee subsequently rules it out for a handball in the build-up.
90' - NO! The space opens up for Dzeko, but he drags his left-footed shot wide of goal!
90'+5 - Goal. Milan score. Cutrone with the finish. 2-1.
KEY MATCH STATS
The Giallorossi now have the international break to contend with - although they will keep busy with a friendly against Benevento next Thursday.
Di Francesco's side are back in action at the Stadio Olimpico the following week, as they host Chievo Verona.
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