Rookie coach Leonardo is under pressure while crowd numbers have been falling and those that remain have openly criticised owner Silvio Berlusconi. Media reports have speculated he could sell the club despite several denials.
Here are the possible scenarios for the future of one of Europe's great soccer clubs.
THE STATUS QUO REMAINS
Milan normally stick with their coaches through thick and thin. Carlo Ancelotti stayed despite the club finishing fifth in Serie A in 2008 and only left in May because Chelsea called.
Apart from their 2007 Champions League triumph, the Rossoneri have stuttered for years and have not won the Italian title since 2004. A few bad results is therefore nothing new.
Leonardo was appointed to replace Ancelotti partly because he was already on the payroll as sporting director.
With Milan cutting costs in the recession, he was a cheap option and to sack him in the short-term would mean a large payout and a big contract for a new coach.
Berlusconi, despite the demands of being Italian prime minister, is still attached to the club after leading them from also-rans to European greats during his 20 years in charge.
Even with finances tight and fans upset by the sale of top player Kaka to Real Madrid and the lack of quality new recruits, he would be reluctant to sell, especially if he would be remembered as the man to offload the club at one of their lowest ebbs.
SACK LEONARDO, APPOINT VAN BASTEN
Despite Milan always taking their time over big decisions, the team's form is so poor that a quick-fix may be the answer.
Leonardo had never been a coach before and is failing to motivate the players, even if he has inherited an ageing squad with little pace.
Luciano Spalletti, who left AS Roma this term, is not allowed to coach another Italian club in the same season so former Milan great Marco van Basten would be favourite to take over despite the Dutchman's patchy coaching record.
However, Van Basten has criticised Milan's lack of buys in the transfer window. Dutchman Frank Rijkaard is another contender.
KEEP LEONARDO, BRING IN BECKHAM AND OTHERS IN JANUARY
Few Milan fans believe their struggles are down to Leonardo. They blame Berlusconi and chief executive Adriano Galliani for not strengthening in the transfer window when Kaka left.
Los Angeles Galaxy midfielder David Beckham looks poised to return for another five-month loan spell from January to try to earn his England World Cup place but more recruits could be needed.
The experienced Beckham would put in the crosses that have been lacking but if Milan were staying frugal in the close season, are they able to change policy in January when the transfer window reopens?
BERLUSCONI SELLS MILAN AND FRESH INVESTMENT BOOSTS TEAM
Media specul
