Milan once again fumbled a lead, this time going from 1-0 up to losing 2-1 at Fiorentina in the last eight minutes.
The Viola needed a boost after a 4-0 defeat to Lazio and midweek 1-1 Europa League draw with Roma, while the Rossoneri were downbeat following a 2-2 stalemate with Verona. Nenad Tomovic and Andrea Poli were suspended, while both sides had lengthy injury lists including David Pizarro, Riccardo Montolivo, Stefan Savic, Nigel de Jong, Mario Gomez, Stephan El Shaarawy, Ciprian Tatarusanu and Adil Rami. Alberto Gilardino got his first start since arriving from Guangzhou Evergrande in January.
Milan were unbeaten at the Stadio Franchi since November 2005, picking up five wins and three draws.
Josip Ilicic curled just wide of the far top corner, while Keisuke Honda fired straight at Norberto Neto’s chest at the near post from a smart Marco van Ginkel assist. Moments later Mattia Destro scuffed his finish in a great position and Jeremy Menez saw his counter-attack deflected for a corner off Aleandro Rosi.
Fiorentina were under pressure early on, but emerged over time and almost scored on the half-hour mark. A free kick found Jose Maria Basanta, whose header cannoned off the crossbar.
The Viola became increasingly dangerous from set plays, Diego Lopez smothering a Borja Valero strike and Gabriel Paletta needing a risky sliding tackle on Ilicic.
Fiorentina stepped up the pressure with Diego Lopez fingertipping a Milan Badelj effort and blocking Joaquin on the resulting corner.
However, against the run of play, it was Milan who took the lead. Giacomo Bonaventura unleashed a wayward shot from just outside the box and Destro smartly redirected it from 12 yards to surprise Neto.
The hosts continue to dominate possession, but without breaking down the resilient Rossoneri, as Philippe Mexes prevented Gilardino nodding in from six yards.
With eight minutes left, Fiorentina did get their equaliser, as Joaquin whipped in a cross from the right for the head of Gonzalo Rodriguez.
The final stages of this game were simply bizarre, as referee Carmine Russo had to be replaced by Paolo Valeri at the 86th minute.
As soon as play resumed, Milan were caught napping and Fiorentina turned the game around completely. Manuel Pasqual crossed for Joaquin, who got in front of Menez for a free header from six yards.