For a club with so much prestige, AC Milan are struggling to win the important matches and Wednesday's Champions League visit of Real Madrid will be as big as it gets this season unless they sort out their problems.
The Group G clash between Europe's two most successful clubs has all the ingredients of a classic encounter, most notably Real coach Jose Mourinho making his first return to the San Siro since leaving Inter Milan after securing the European Cup.
Milan's Ronaldinho, an old adversary of Real from his glittering spell at Barcelona, is also hoping to make a decisive comeback from injury and stop the visitors sealing their place in the last 16 with a first win at the famous stadium.
A long-term injury to former Milan man Kaka halts the fairytale but the second-placed hosts should still have hearts racing. Instead, Milan, seven-times winners, appear a bag of nerves.
First, Real completely steamrollered the Rossoneri in the first quarter of the Bernabeu group game with the red-hot Cristiano Ronaldo and Mesut Ozil scoring within a minute to wrap up an easy 2-0 win.
Then they were beaten 2-1 at home on Saturday by rivals Juventus, a team which managed to find the extra-motivation for a classic match — something injury-hit Milan seem to lack.