Arsenal were handed a two-legged battle against Italian Champions AC Milan in the last 16 of the Champions League today.
The first leg will see Arsenal travel to face Milan in the intimidating environment of the San Siro on Wednesday February 15th. It may be the day after St Valentines Day, but there will be little love for the Gunners in the notoriously hostile Milan crowd.

Having been knocked out of this competition for two years running by FC Barcelona, Arsenal fans will at least be grateful that they get to avoid the defending European champions for one round at least.

Having won UEFA Champions League Group F, Arsenal could have been drawn against FC Basel, Zenit St Petersburg or Olympique Lyonnais. When you look at the teams who qualified as group runners up in the group stages, a draw against AC Milan is about a tough as it could have been.

Milan qualified from Group H with a game to spare, finishing second only to Barcelona. Milan did achieve a 2-2 draw with the Catalan giants to open group play, showing what a tough prospect they could be for the Gunners.

Milan are also the defending Serie A champions, and are only two points behind league leading Juventus in this years table.

When you take all this into account, it would be fair to ask what reason Arsenal have to be optimistic ahead of their trip to Italy in February?

The first reason would be that this is the fourth time that Arsenal have been drawn against Italian opposition in the UEFA Champions League knockout stages, and the Gunners have been triumphant on every other occasion.

Arsenal were drawn against Serie A leaders Juventus in the quarter-finals of the 2005/2006 UEFA Champions League. Goals from Thierry Henry and Cesc Fabregas led Arsenal to an impressive 2-0 aggregate win.

The Gunners were drawn against AC Milan in the last 16 of the 2007/2008 Champions League. After a 0-0 draw in north London during the first leg, late goals from Fabregas and Emmanuel Adebayor gave the Gunners a 2-0 win at the San Siro to qualify for the quarter-finals.

During the 2008/2009 competition, Arsenal were drawn against Roma, and won on penalties after a 1-1 aggregate draw to eliminate the Italians.

One more happy memory of the San Siro for Arsenal, is the day that the Gunners went to face Inter Milan during the 2003/2004 tournament. Henry was on fire that day, and his brace highlighted what many believe what was Arsenal’s greatest performance in Europe under Arsene Wenger. Freddie Ljungberg, Edu and Robert Pires also scored as the Gunners battered Inter 5-1.

It is also worth bearing in mind that Milan are looking to avoid being eliminated from Europe’s premier competition at the hands of English opposition for the third straight year.

During the 2009/2010 Champions League, Milan were hammered 7-2 on aggregate by Manchester United, while last season they were beaten 1-0 over two legs by Tottenham Hotspur.

It would be wise for Arsenal to respect AC Milan when they travel to Italy, but it is clear that they should not fear them.