Fiorentina 1 AC Milan 1: Calhanoglu earns stuttering Rossoneri a point
Gennaro Gattuso's side overcame fierce rivals Inter 1-0 in the Coppa Italia on Wednesday but it looked as though they would fall to a third straight league defeat without scoring when Simeone headed in Cristiano Biraghi's excellent cross in the 71st minute.
However, the lead lasted just three minutes as Calhanoglu fired home a rebound from close range, meaning the Rossoneri avoided going three straight Serie A games without scoring for the first time since November 2001, when Gattuso was tearing around the Milan midfield with trademark tenacity.
A generally dour affair belatedly came to life after an initial 70 minutes that were only notable for Gianluigi Donnarumma impressing on his 100th appearance for the San Siro giants.
A groin injury meant elder brother Antonio had taken his place against Inter but Donnarumma Jnr was back at the Stadio Artemio Franchi, where he made saves from Simeone, Gil Dias and Milan Badelj either side of half-time.
He had no chance of keeping out Simeone's powerful header, but Calhanoglu's speedy reactions ensured the Viola conceded for the first time in 499 league minutes and rescued a point for Milan.
Triplice fischio al Franchi, #FiorentinaMilan 1-1
@simeonegiovanni
@hakanc10 pic.twitter.com/YtwMRnxcwj
— ACF Fiorentina (@acffiorentina) December 30, 2017
The tone for a largely turgid encounter was set early on but, after 39 minutes produced almost nothing by way of goalmouth action, there was a moment of controversy when Simeone was brought down as he looked to burst through on the edge of the box.
Alessio Romagnoli received only a yellow card for his foul and Jordan Veretout crashed the free-kick into the wall.
Three minutes later Donnarumma raced from his line to smother at the feet of Simeone and in stoppage time the goalkeeper parried Dias' header up and onto the crossbar as Fiorentina ended the half strongly.
Donnarumma picked up where he left off two minutes into the second period, getting down low to his right to keep out Badelj's curling effort.
99+1=
@gigiodonna1 #FiorentinaMilan #weareacmilan pic.twitter.com/UpgffgPYM7
— AC Milan (@acmilan) December 30, 2017
The visitors' attack belatedly kicked into gear shortly afterwards as Suso cut in on his left and unleashed a shot that Marco Sportiello tipped over.
Simeone then left Donnarumma with no chance, rising unmarked to nod in from close range, but the lead was rapidly wiped out as Sportiello parried Suso's effort into the path of Calhanoglu, who smashed into the roof of the net.
Sportiello denied substitute Andre Silva in the final minute of normal time as both sides were forced to settle for a share of the spoils - a fifth draw in the Viola's seven-match unbeaten run.