Date: 22nd December 2009 at 8:39pm
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United playing Milan in the Champions League was not exactly something I had been eager to see. Still, the draw brought us the Italians and in my opinion it’s a fabulously unpredictable tie. Everything can happen.

The most important question is, of course, this: are Milan better than United? And the answer is an obvious, resounding no. They were embarassed by Werder Bremen in the San Siro in the Europa League last season while United were busy getting to their second successive Champions League final. Their best players are over the hill and Leonardo is no Carlo Ancelotti.

Still, I would not consider United favourites. Some of our best players – most notably Paul Scholes and Ryan Giggs – are also past their best and if Pirlo, Seedorf and Ronaldinho feel up to playing a little football then they are not nearly bad at it. It’s just that they cannot really find the motivation any more to put themselves about against unfancied teams with nothing more than three points to play for. A Champions League clash against Manchester United is not such a mundane event, though.

And of course there’s the fact that Milan are our bogey team: we never won a two-legged European tie against them. Of course what happened in the sixties is hardly relevant now but there’s plenty to remember from the last four meetings, three of which were won by Milan. But not many conclusions can be drawn from those games, in all honesty because circumstances were very different.

In 2005 when Milan twice beat us 1-0 they were clearly and undeniably a better team. They had an impressive aura about them in Europe and they were very shrewd and experienced. United, meanwhile, were ordinary throughout that campaign: Paul Scholes and Ryan Giggs were off colour for months, Roy Keane was past his best, Ruud van Nistelrooy was struggling with injuries all season and Ronaldo and Rooney were still very inexperienced. We could not break them down at Old Trafford and went down thanks to a Carroll gaffe and were outplayed in the San Siro, losing 1-0 with a Hernan Crespo goal.

The 2007 semi-final was a different affair though: throughout that season United were a lot, lot better than AC Milan. We played with zest, vigour and invention and thoroughly deserved to get the Premier League crown from back Chelsea’s grasp. Milan, meanwhile, were struggling following the departure of Shevchenko (and the aging of their other stars) and were way off the pace even in a league almost destroyed by calciopoli. Eventually they finished some 35 points behind Inter Milan…

But they won that tie because they had Kaka in the form of his life and because they could afford neglecting league fixtures in favour of the best possible preparation for this big, big game. United had no such option: we had a thin squad fighting for the title and the effects of a gruelling season were way too obvious in Milan as we were destroyed 3-0 by a side clearly fresher and more focused.

But this time the tie is brilliantly poised. With Ancelotti gone from Milan, perhaps some of their psychological hold over us will disappear, too. Neither side is clearly superior this time and neither should be less fresh or focused than the other. On the balance of this, we have a somewhat stronger squad (but a lot depends on Ronaldinho, Seedorf and Pirlo who are the best three Milan players by miles) and an infinitely more experienced manager – and we have the advantage of playing the second leg at home. So, we should really be confident.

Why am I not? Well, because in 2007, in the San Siro, we faced Milan with a back four of Brown, a half-fit Vidic, Heinze, O’Shea – in other words, a makeshift back four. Had Ferdinand, Evra and Neville been available we would have stood a chance. And as things stand, this time we might be forced to use midfielders at the back… I know it’s still months away and the defenders should be back in action but you never know with us today – it’s easily conceivable that we’ll have six or seven defenders out when we visit Milan. And if we do, we’ll lose.