The Italian Job - Why AC Milan Must Beat Arsenal And Avoid A Fourth Straight Champions League Exit To An English Club

In the end, it was kind of inevitable. AC Milan’s chances of being drawn against an English side in the last 16 of the Champions League had been vastly reduced by the group exits of Manchester United and Manchester City, but still they will be forced to confront head-on their recent travails against teams from football’s motherland after being paired with Arsenal at the same stage as in 2008.

Until that clash with Arsene Wenger’s side four years ago, Milan remained one of the teams to beat in Europe. With triumphs in 2003 and 2007, they still had a clear thirst for winning ‘Old Big Ears’. And along the way they’d largely taken ties against English clubs in their stride.

Their two wins over Manchester United in 2005 – both earned by solitary Hernan Crespo goals – helped lead Carlo Ancelotti’s side to the final in Istanbul. There, they would largely dominate Liverpool, taking one of the more dominant positions ever known in a European Cup final, only to be outdone by six minutes of madness in the second half.

They proved that was little more than an aberration 24 months later in seeing off Rafael Benitez’s side in Athens to gain their seventh European title, but as it turned out, it marked the end of an era.

Since that high there has been nothing but pain for the Rossoneri in their clashes with England’s finest, with their last three Champions League campaigns having been ended by Premier League representatives. There are lessons to be learned from each of their exits if they are to set things straight in February and March.

Last time they faced Arsenal they took far too much for granted. For an experienced double Champions League-winner, Ancelotti let his men get away with far too much cautious play in the first leg at the Emirates. It was almost as if they believed they were a stick-on to win the home fixture two weeks later. They didn’t. Instead they were hammered into submission, with late goals by Cesc Fabregas and Emmanuel Adebayor the worthy reward for Arsenal’s superiority.

While Zeljko Kalac’s error on Fabregas’ strike from range was picked out as the key moment by some, the real fault was with the hierarchy. Training plans were altered, diets were changed and targets were refocused to go all-out to win the Club World Cup. Once that was achieved, the season was a near non-event. Out of the Champions League and playing catch-up in Serie A, Milan left it too late to launch a comeback. Finishing fifth, they found themselves playing Thursday night football the following year.

By the time Clarence Seedorf’s late strike had been added to Ronaldinho’s third-minute opener, United had netted three times and the tie was over. Leonardo had been punished for allowing his side to be wide open at the back, and the severity of their 4-0 second leg defeat was no great surprise.

One year on, they had at least learned their lesson at the back, with new coach Massimiliano Allegri feeling the benefit of Thiago Silva having grown into his role as the leader of the defence, and with Ignazio Abate having been nurtured into a right back of some talent. But still their old failings in the forward line made them pay. Tottenham showed great resolute and simply weren’t tested enough at San Siro.

Peter Crouch’s snatched winner, from Aaron Lennon’s burst down the right, gave Spurs a vital away goal, despite the fact that Milan had dominated much of the possession and territory. Knocked off their stride by pace once more, they didn’t have enough of their own to trouble Spurs. Even when they made all the running in an improved second-leg display, they couldn’t quite finish off the job. Alexandre Pato missed two great opportunities and Harry Redknapp’s men progressed.

This time around, they should have the tools available at least. Kevin-Prince Boateng was just returning from injury at White Hart Lane last March, but now represents a key figure in their forward play. His extra energy, strength and heart is just the kind of quality Milan have missed over the last four years. Their tally of two goals in six matches against the Premier League’s finest says a lot, and looking beyond that stat you’ll find that those goals – both in the 2010 first leg against Manchester United – came at times when the opposition were caught off guard.

Arsenal’s defensive troubles at times this season suggest Milan will have a chance to gain a first-leg lead this time, but Zlatan Ibrahimovic & Co. need to make it count. Healthy periods of possession have to be made the most of. As Allegri and the Milanese press have rightly asserted since the draw was made on Friday, these clubs are just about on an equal footing. While both play good football, it could be a real joust at times, and the victors will be that side that are more clinical. Arsenal have been exactly that of late thanks to Robin van Persie. Therein lies a lesson.