UEFA Champions League Draw: Arsenal FC Earn Toughest Assignment vs. AC Milan

Take a quick glance at the draw for the 2012 UEFA Champions League Round of 16 and guess which of the clubs on the right will have the most difficult pairing.

Olympique Lyonnais FC (France)	APOEL FC (Cyprus)
SSC Napoli (Italy)	Chelsea FC (England)
AC Milan (Italy)	Arsenal FC (England)
FC Basel 1893 (Switzerland)	FC Bayern Munich (Germany)
Bayer 04 Leverkusen (Germany)	FC Barcelona (Spain)
PFC CSKA Moscow (Russia)	Real Madrid (Spain)
FC Zenit St. Petersburg (Russia)	SL Benfica (Portugal)
Olympique de Marseille (France)	FC Inter Milan (Italy)

Did you guess Arsenal?

Well then, ding, ding, ding! We have a winner!

Or not.

As a reward for ousting Udinese in a playoff to get into the group stage—and for subsequently winning Group F—the Gunners will face the Italian juggernaut AC Milan, the reigning champions of the Serie A.

The Rossoneri may not be the most imposing challengers possible, although they still boast plenty of world-class talent. The talent extends from Zlatan Ibrahimovic and Kevin-Prince Boateng to the Brazilian trio of Robinho, Thiago Silva and Alexandre Pato—not to mention a host of top-tier players from "The Boot."

Now, some would argue that Chelsea, Arsenal's North London rival, actually earned a tougher draw. They were against a Napoli side that took four points from English Premier League-leading Manchester City. The Azzurri's attack of Edinson Cavani, Marek Hamsik, Ezequiel Lavezzi and Goran Pandev is among the most dangerous in all of Europe right now.

But that squad has yet to win a single trophy, at home or abroad. They have never competed at the highest level of European club football. A short-lived foray into the Europa League last year constitutes the bulk of their continental experience.

Milan, on the other hand, have been there and done that. The Rossoneri are practically permanent residents on the European Cup circuit and are replete with star players who've performed on the biggest stages in the world under the brightest lights.

Surely, the Gunners won't be intimidated. Few managers in football today are as well-versed in balancing the demands of various competitions as Arsene Wenger, who's guided Arsenal to 15 consecutive Champions League berths. It certainly helps his side's case that he'll have at his disposal arguably the hottest striker in the world right now in Robin van Persie.

But the back line is in poor fitness, as it has been all season, and the attack drops off considerably behind RVP.

Still, the Gunners clearly have their work cut out for them if they're going to advance to the quarter-finals of the Champions League.

Then again, it's only fitting that, amidst a 2011-12 season marked by tremendous challenges both on and off the pitch, Arsenal would be faced with yet another daunting obstacle.

No challenge has been able to stop the Gunners completely. Who's to say Milan will be the first?

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