AC Milan needed a 90th-minute penalty to claim a point in a manic 3-3 draw Sunday against relegation-threatened Frosinone.
Despite the effort, Milan is now down to seventh place in the Serie A standings. Sassuolo beat Hellas Verona 1-0 to move past the Rossoneri, putting them at a real risk of missing Europe for a third consecutive season.
"We struggle in the must-win matches and we don't know why," said defender Luca Antonelli. "We needed a win today to keep Sassuolo behind us. We now find ourselves chasing and that is far from ideal."
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A rainy Sunday at the San Siro couldn't have started off worse. Luca Paganini scored within two minutes to give Frosinone an early lead, and Oliver Kragl doubled the advantage with a free-kick from long range. Teenage goalkeeper Gianluigi Donnarumma showed his inexperience on both goals, but his teammates were no better on the other side of the pitch.
Milan fired 11 shots on target - the most in a single Serie A match this season. Mario Balotelli also missed a penalty, and hit the crossbar just before the final whistle.
Then down 3-1, the Rossoneri appeared out of luck. But Antonelli surprised everyone with a perfectly executed bicycle, and that allowed substitute Jeremy Menez the opportunity to score the equaliser from the spot at the end of regular time.
Cristian Brocchi has now overseen just one win in four matches in charge of Milan.
"We played for the win right until the end. The performance today is there for everyone to see. We put in a good performance, we created chances, but at the same time we cannot concede three goals at home," said Brocchi.
It is only the second time Frosinone has scored three Serie A goals in a single game, with the other occasion coming against the already relegated Verona. The Lazio-based club is likely to join Verona in Serie B despite the result.
Milan's only realistic hope of qualifying for the Europa League rests on what it can do against Juventus in the Coppa Italia final on May 21. A Milan loss would hand the European berth to the sixth-place finisher.