Teenage goalkeeper Gianluigi Donnarumma produced a last-gasp stop to save AC Milan's blushes in a scoreless draw with relegation-haunted Carpi that compounded the Serie A giants' Europa League hopes on Thursday.
A win against the league new boys would have pulled Milan to within four points of fifth-placed Fiorentina and kept them firmly in contention for a place in next season's Europa League.
But Milan failed to fire, completely missing their few opportunities on goal and had to rely on Donnarumma to produce a great stop in the dying minutes when Marco Crimi unleashed a left-footed curler that was heading for the top corner.
Feted by the club last week when Milan claimed their first win under his helm, newly-appointed coach Cristian Brocchi dropped his first points since replacing sacked Sinisa Mihajlovic barely two weeks ago -- and fans were quick to respond by whistling the misfiring Rossoneri off the pitch at the San Siro.
Milan remain in sixth place at 29 points behind leaders and champions-in-waiting Juventus, who beat Lazio 3-0 on Wednesday to maintain their nine-point cushion on Napoli with four games remaining.
But qualification for Europe's second tier competition -- once unthinkable for a club that has been crowned European champions seven times -- is becoming difficult, especially with Sassuolo only four points adrift in seventh.
Now six points behind Fiorentina, Milan have two chances to play European football next season: beating Juventus in the final of the Italian Cup final -- the victors of which are given a spot in the Europa League -- or making sure they finish in sixth place.
If Juventus, who have already qualified for the Champions League, win the final in Rome on May 21, the Europa League spot will go to the sixth place finisher.