AC Milan's Champions League Return Faces Tough Challenges in Group C

(Photo by Valerio Pennicino/Getty Images)

If you told Milan supporters before the summer that not only would they lose superstar Kaka in a sale to Real Madrid, their former hero would also be suiting up for the visitors at the San Siro only a few short months after, they probably wouldn't have believed you.

But in an ironic twist of fate, it's only fitting that European heavyweights A.C. Milan and Real Madrid will square off in group C in the first stage of this year's Champions League, along with Olympique de Marseille and FC Zurich.

Even under normal circumstances, European draws between Milan and Madrid—the two most successful clubs in the tournament's history—are enough to salivate over. But throw in the Kaka summer transfer saga and October 21 and November 3 will no doubt provide some of the most interesting moments of this season's group stage.

Despite what the two clubs have in common though, they really couldn't be further apart as far as expectations.

Real Madrid completely revamped their squad by throwing unprecedented amounts of money at the likes of Kaka, Cristiano Ronaldo, and Karim Benzema, instantly making them favourites for the title, along with defending champions Barcelona.

A.C. Milan, on the other hand, were almost non-existent in the summer transfer market, and have been struggling to deal with some traditional years since they last lifted the Champions League trophy in 2007.

After a disastrous preseason and little hope in the way of new arrivals to propel the team past their disappointing third place finish in Serie A last season, it's hard to see A.C. Milan matching the level of competition Real Madrid will bring.

So what will Milan's European adventure look like this year?

Vice-president Adriano Galliani is already starting to play down the hopes of Rossoneri fans.

"Milan was in Pot One and picked up the toughest team from Pot Two," he told Sky recently. "I would have preferred facing (Madrid) later; they have been the transfer market kings."

Getting out of the group stage is a realistic expectation, but assuming the team will struggle against Real Madrid, there will be no room for error against the lesser sides. And given the fragile confidence of this team, an upset by dark-horses Marseille might not be out of the question.

Milan's biggest troubles lie in the midfield. The aging A.C. Milan core is simply too slow to keep up with the likes of Real Madrid's Cristiano Ronaldo, Kaka, Lassana Diarra, and Xabi Alonso.

Without Kaka, Milan's hopes rely squarely on Ronaldinho's shoulders, whose critics are looking more and more correct about his declining impact on the game. Milan can no longer afford to move him to the wing either, with nobody else really capable of playing in an attacking midfield role.

Gattuso has looked even worse—a shadow of the player that shut down Cristiano Ronaldo in the 2007 Champions League semi-final. He was awful in the club's embarrassing 4-0 loss to Inter, and will need to find a way to be effective again soon if Milan has any chance at competing in the middle of the pitch.

On the wing, it's more of the same for Milan. Ambrosini is still effective in a defensive role but both he and Clarence Seedorf are starting to show their age.

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