AC Milan crashed out of the Coppa Italia at the quarter-final stage as they lost 2-1 to Atalanta at San Siro on Wednesday night.
Things seemed to be going in the right direction for Milan when Rafael Leao’s fantastic finish in the closing stages of the first half made it 1-0, but Teun Koopmeiners equalised within 90 seconds.
Koopmeiners would sting the Rossoneri again in the second half and this time from the penalty spot after Alex Jimenez was controversially penalised for a foul on Miranchuk. The Dutchman converted from 12 yards, and it would prove to be the winner.
Milan’s Coppa Italia drought will therefore continue, and it is a bitter blow given that many saw the competition as a legitimate trophy target given the teams eliminated already.
Stefano Pioli made four changes from the team that beat Empoli 3-0 at the weekend with Matteo Gabbia and Alex Jimenez coming into the back four, Yunus Musah getting a start in midfield and Luka Jovic leading the line.
The opening exchanges were perhaps befitting of two local rivals looking to seal the third spot in the semis of the competition. The only briefly threatening moment in the opening 10 minutes was a cross from the left that Musah looked to get onto but it was well cleared.
It was a battle between two teams who are certainly no stranger to the high press and a midfield stalemate seemed to break out with both sides struggling to hang onto the ball.
The first real moment of danger came in the 18th minute when Ruben Loftus-Cheek won back possession inside Milan’s half and Christian Pulisic led a break which ended with Musah seeing a shot parried over after Rafael Leao’s cut-back.
De Ketelaere had been tracked and contained by Gabbia inside the opening half hour, but he could have had an assist with a lovely floated cross from the left side that was volleyed well over from an unmarked position.
Atalanta had a huge opportunity to take the lead a few minutes later and again De Ketelaere was involved. A deep cross to the far post was nodded by across goal by the Belgian towards De Roon, who bashed into Gabbia with his run and the ball drifted just wide.
The fall-out from the incident was not done there though as Gasperini was sent off for his protests at the lack of a penalty, while Gabbia had to go off with a bloody nose and was replaced by Simon Kjaer.
With seconds left of the first 45 minutes, Milan took the lead. Maignan claimed a corner and Tijjani Reijnders fed Leao on the break down the left, who fed Theo Hernandez and received a return ball before slamming a finish first time inside the far corner.
However, the lead wouldn’t even last until half time as Atalanta got themselves level pretty much straight from the restart. La Dea built down the right with Miranchuk and De Ketelaere, finding Holm who pulled the ball back to Koopmeiners who fired past Maignan with a low angled shot.
The away side could have even been leading going into the interval but Calabria made a very impressive block to deny the ex-Milan loanee Pasalic who seemed certain to score from around the penalty spot.
La Dea had the first chance of the second half too, with Koopmeiners letting fly from around 25 yards and drawing a good save from Maignan. A counter ensued from the resulting corner but Leao’s through ball couldn’t quite find Calabria’s run in behind.
Koopmeiners continued to be the main threat for Atalanta as we suggested he might be in a pre-match article, and he dragged a shot wide from the edge of the box on 55 minutes.
Minutes later, Atalanta got themselves in front and it came from the penalty spot. Miranchuk took on Jimenez with a dart to the byline and went down despite the fact the Spaniard got a touch on the ball, and Koopmeiners sent Maignan the wrong way from 12 yards.
On the hour mark Pioli made a couple of changes, with Filippo Terracciano coming on for his debut alongside Jan-Carlo Simic, with Jimenez and Calabria being withdrawn.
The Bergamo side were the team who responded better to the goal, with De Ketelaere seeing an effort from close range squirm into Maignan’s hands before the Frenchman gratefully caught a shot from 20 yards not long after.
Musah hadn’t had the best of games in truth, though he did well to block a shot from Ederson that looked to be heading into the bottom corner. At the other end, Pulisic forced a great save from Carnesecchi.
On 72 minutes Pioli made a couple more changes with Loftus-Cheek and Reijnders coming off for Yacine Adli and Olivier Giroud in what was a clear switch to a two-striker system.
Inside the closing stages Leao tried to return the favour to Theo after his previous assist with a cut-back inside the box that the defender charged onto but laced into the crowd.
Milan tried to force an equaliser in the closing stages but they never moved the ball quick enough nor produced quality deliveries, and the result was another early cup exit.