AC Milan’s already slim hopes of making the top four were dealt perhaps a decisive blow as they lost 2-1 against Bologna on Thursday night.
The home side had the better of proceedings in the first half but it was Milan who went in a goal up thanks to Rafael Leao.
A flick-on from Santiago Gimenez was collected and he rounded the goalkeeper to slot in just before the break.
The Rossoneri fell apart in the second half, though, with Santiago Castro first equalizing from close range after a free kick found its way to him and Dan Ndoye finishing the comeback with a goal from a few yards out.
Milan is now eight points behind Juventus in fourth place and three behind their hosts Bologna, meaning that any hopes of qualifying for the Champions League are now definitely gone bar the shouting.
Christian Pulisic was benched and Youssouf Fofana returned to the starting lineup, marking Sergio Conceicao’s only alteration from the squad that lost to Torino on Saturday.
It required a reorganization, with Joao Felix and Santiago Gimenez up front and Yunus Musah nearer to the right.
Milan got off to a strong start and had a half-open first sixty seconds.
Perhaps a bit behind him, Musah found Gimenez with a ball, and the Mexican’s left-footed attempt went over the bar.
After putting in his own net against Torino, Malick Thiaw came very close to another humiliating own goal during the hectic start at the Stadio Renato dall’Ara, but he knew far less about that one.
In the early exchanges, the right side was more prominently involved.
After being located by Jimenez, Musah made a save from Skorupski’s knees from a close angle, but it was actually a narrow angle.
In the 25th minute, the Rossoneri had a genuine chance when Theo Hernandez was substituted out without a free kick.
Ferguson then found Ndoye running in behind, but Strahinja Pavlovic did just enough to knock him off balance as he shot.
With Mike Maignan making what can only be described as a reaction stop to keep out a cross and Fofana having penalty appeals waved away after coming down inside the area, the game remained end-to-end.
Eight minutes before to halftime, Maignan was called upon once more when Dominguez, who was fed by Ndoye on the left side of the box, easily ducked past Alex Jimenez but fired a close-range effort at the goalie.
Rafael Leao gave Milan the lead with just over two minutes remaining before halftime. Gimenez skillfully flicked on a long ball from Maignan to find the Portuguese winger running in behind, who turned Skorupski and tapped in with his left foot.
Milan changed their defensive strategy in the second half, and Bologna equalized the score in less than three minutes.
Fabbian’s chest-down was shot in from close range by Castro after Theo gave up a free kick and a yellow card on the left side.
Both an offside and a handball on the assist were appealed, but they were dismissed, therefore the score was 1-1.
Then, without really generating many clear-cut opportunities, Bologna seized the lead.
However, one hour in Conceicao decided to alter the attack by substituting Christian Pulisic for Felix.
Bologna were very close to taking the lead twice in quick succession when Casale’s glancing header from a corner crashed off the post and then Cambiaghi connected sweetly with the rebound but sent it just over the bar.
They were not to be denied on their next attack though as Ndoye put the home side in front. Cambiaghi sent in a wonderful cross from the left side and Pavlovic was beaten to it at the near post, with Ndoye stabbing home from close range.
A final roll of the dice followed from the Milan coach with Jimenez – who had appealed that the ball went out in the build-up to the second Bologna goal – came off for Tammy Abraham.
With Casale’s glanced header from a corner crashing off the post and Cambiaghi’s lovely connection with the rebound but just over the bar, Bologna came extremely close to grabbing the lead twice in rapid succession.
However, Ndoye put the home team ahead on their following attack, so they couldn’t be stopped.
Ndoye scored from close range after Cambiaghi’s brilliant cross from the left side was beat to the near post by Pavlovic.
The Milan coach then made one more decision, and Jimenez, who had argued that the ball had gone out during the build-up to the second Bologna goal, was replaced by Tammy Abraham.