I think everyone will agree that this is a less then ideal draw for us. They are the current leaders in Serie A and one of the most successful clubs in history. Milan has won 18 officially recognized UEFA and FIFA international titles, and remains tied with Boca Juniors as having won the most in the world. Milan has won this same European Cup/Champions League on seven occasions; only Real Madrid has exceeded this total. Domestically, Milan has won 17 league titles, making the club the third most successful in Serie A behind local rivals Inter (18) and record-holder Juventus (27). Right now they aren't the powerhouse that they have been in the past, but still, I feel like there were easier teams available then Milan. Their history alone is staggering.
Milan were in the same group with Real Madrid, Ajax, and Auxerre. Ajax and our Group A opponent, Twente, are very close to each other in the Dutch standings. Milan won their home match against Ajax and drew their away match against Ajax with a +2 goal difference. We won our home match against Twente and drew our away match against Twente with a goal difference of +3. That comparison is pretty much identical.
Let's compare their results against Real Madrid, Milan's seeded group team, and Inter, our seeded group team. Milan lost away to Real Madrid and drew them at home with a goal difference of -2. We lost away to Inter but beat them at home with a goal difference of +1. Although Spurs fared better, Real Madrid is a much better team and when we faced Inter they weren't playing well, so I don't see much difference here either.
Here's the statistic that concerns me the most: goals conceded. They lost their final meaningless group game, so in the 5 meaningful matches (including 2 against Real Madrid), they only gave up 5 goals. 4 of them were to Real Madrid. Currently, they have conceded the fewest goals in Serie A. Unlike our games, they seem to play a very tight and organized game. We've been successful so far in this tournament because we've been allowed to play a wide open game. When other teams in the English Premier League have "parked the bus" and tried to defend first, we've had trouble breaking them down. I think this will be the deciding factor in our home and away match up with Milan. If we have trouble breaking them down, I think it will be difficult to advance in a low scoring affair. We always find a way to concede a goal but score more to offset the error(s). That might not happen this time. However, if Milan are similarly slow to Inter, we may be able to overcome this with speed and physicality.
One positive of this draw is that Milan and Inter share the same stadium. We've already played once there against Inter, so we should already know what to expect from the time we leave London until we return. Additionally, it will be a great night at White Heart Lane against a storied club when we host them. We probably would have preferred someone else, but they wouldn't have the same history as Milan does. As group winners, we will travel to Milan first and then host the second game (same order we played Inter). I like this because it sets the second and deciding game at home. In the first match away all is not over even if you lose...and a scoring draw is like a win due to the away goals rule.
In summary, I think this is going to be very tough and too close to call. Right now, I'd call it 50/50. We face Milan in February, and by that time, who knows how each team will be playing.
