Mario Balotelli and Philippe Mexes scored late on at Siena as Milan came from behind to secure a place in the UEFA Champions League.
Balotelli’s late penalty had cancelled out Claudio Terzi’s first-half header, before Mexes netted a crucial winner.
A hard-fought second half saw both sides reduced to 10 men in the space of just a few minutes after Massimo Ambrosini and Christian Terlizzi were both sent off for second bookable offences.
But it was the late goals that made all the headlines as Milan guaranteed their place at European football’s top table in dramatic circumstances.
Milan came into the game needing to win in order to beat Fiorentina to the final UEFA Champions League place, and they made five changes to the team that played out a controversial 0-0 draw with Roma last week.
Sulley Muntari’s bizarre red card in that game meant that he was suspended, while Ignazio Abate was preferred ahead of Kevin Constant.
Robinho, Antonio Nocerino, Riccardo Montolivo and M’Baye Niang were all handed starts.
Siena, whose relegation was confirmed with a 2-1 loss away to Napoli, welcomed back Alessandro Rosina.
Milan began the game with an expected level of urgency, creating a flurry of chances during the opening exchanges.
Balotelli was the first to test Gianluca Pegolo in the Siena goal, seeing his stinging long-range effort tipped over the crossbar.
A few moments later, Cristian Zapata saw a header cleared off the line before Brazilian Robinho was unlucky not to break the deadlock when he saw his vicious swerving shot palmed away by Pegolo.
And Milan were made to pay for their profligacy just before the half-hour mark when the hosts took an unlikely lead through Terzi.
A pinpoint free-kick from Rosina found the head of the defender, who took advantage of some slack Milan marking to direct his header past Chrisitan Abbiati.
Milan nearly conjured up the perfect response just two minutes later, when Balotelli crashed a shot onto the crossbar.
And the Italian was involved again just before half-time, forcing a decent save from Pegolo as Siena weathered the
The second half began in similarly frustrating circumstances for Milan, as they struggled to find a decisive final ball. And 10 minutes later they were down to 10 men when Ambrosini slid in rashly on Adrian Callelo and was shown a second yellow card.
The numbers were even soon after, though, as the home side were also down to 10 men – Terlizzi given his marching orders for jumping into a challenge with Balotelli.
Balotelli made his mark in some style 10 minutes from time when he was brought down in the box by Felipe to give Milan hope.
The Italian brushed himself down to calmly slot home the resulting spot-kick and the comeback was on.
Then, with just two minutes to go, Mexes found himself on the end of a Montolivo cross to slot home the dramatic winner.