Antonio Di Natale's penalty proved to be Udinese's match-winner against Milan
The writing appears to be on the wall for AC Milan coach Massimiliano Allegri as his side suffered a third defeat in four Serie A games at the hands of Udinese.
The beleaguered Rossoneri boss has spent the last fortnight deflecting speculation his job is under threat and will now face more tough questions should he remain in charge at the San Siro.
Udinese put their opponents under the cosh with a Mathias Ranegie goal just before half-time, with Stephan El Shaarawy restoring some confidence for the visitors in the second period with a mercurial finish from 25 yards.
But as Cristian Zapata became the first of two Milan players to be dismissed, Kevin Prince-Boateng later walking for two yellow cards, Antonio Di Natale converted from the penalty spot to earn the Zebrette their first three-point haul of the new campaign and cast Allegri's future into serious doubt.
Riccardo Montolivo dragged a half volley beyond a post as Milan sought a quick solution to their butterflies.
Giampaolo Pazzini forced a solid save from Zeljko Brkic at his near post before Phillippe Mexes tested the Udinese goalkeeper with an overhead kick from the resulting corner.
Di Natale scuffed a couple of chances to frustrate providers Roberto Pereyra and Giampiero Pinzi, and soon Montolivo tried his luck from 25 yards at the other end.
Christian Abbiati had to be at his best to deny Mehdi Benatia from six yards following Di Natale's cut-back but the Zebrette would take the lead five minutes before the break.
Swedish striker Ranegie leapt above Abbiati and Mexes to nod the Friulians into the lead and crank up the pressure on Allegri.
It was nearly two shortly after the interval as Marques Allan unsettled Abbiati with a snapshot.
Milan got the goal their early dominance merited in the 54th minute as El Shaarawy produced a strike of real quality to level the tie.
Prince-Boateng pulled off a defence-splitting pass to Pazzini, the Italy striker deftly teeing the ball up for an onrushing El Shaarawy to launch it into the back of the net.
Zapata conceded a foul for handball, earning a yellow card for his troubles, and soon Abbiati had throw up his glove to repel Di Natale from the ensuing free-kick.
And in the 67th minute, Zapata walked, fouling Ranegie as he roamed in on goal. Di Natale gladly stepped up to rattle home his third goal of the season from the spot.
Milan's response to the double setback was ponderous and it fell to Pazzini to take the initiative and drill powerfully against Brkic.
But the Rossoneri were wounded further in the 82nd minute as Boateng received his second yellow card and his marching orders for a tussle with Pereyra.
Milan were now down to nine men and shorn of confidence, and substitute striker Bojan slipped as he prepared to take one last corner kick, Brkic slowly walking over to collect the loose ball.