5 Best Arsenal performances against Italian sides in Europe

AC Milan (2007/08)

Adebayor saw his effort clatter off the crossbar

Arsenal were drawn against an Italian outfit again in 2007/08's round of 16 in the form of AC Milan. Milan were reigning champions, having defeated Liverpool 2-1 in the 2007 final.

The Gunner's youthful side had its skeptics after losing star player Thierry Henry to Barcelona in the previous summer but they appeared determined to showcase their talents on the European stage, especially against such an experienced side.

The Emirates was the hosting ground for the first leg, a match that ended 0-0. It was a tactical battle more than a thrilling one in England's capital.

Arsene Wenger's team dominated early proceedings with Togolese centre forward Emmanuel Adebayor causing trouble for the visitors' defence but to no avail thanks to a number of classy stops from seasoned veteran Kalac in the Milan goal as well as the linesman who correctly flagged the striker offside after he slotted home.

Adebayor was granted with a golden opportunity late on after the rapid Theo Walcott delivered a beautifully weighted cross that the Togo international could only nod onto the crossbar.

The woodwork shook and the whistle blew as Arsenal blew their chance to take an advantage to Milan.

The young Arsenal side went into the second leg at the San Siro with no fear, going for the jugular from minute one. Cesc Fabregas ran the game, coming agonizingly close after he hit the crossbar just before half-time.

However, it was the aforementioned Fabregas who broke the deadlock, wrong-footing Kalac with a 30-yard thunderbolt in the 84th minute. Theo Walcott then found Adebayor with a pass in the last few minutes of the game, who made no mistake this time, turning the ball into the net at the back post.

The result meant that Arsenal had beaten both Milan sides at the San Siro within the space of five years, having emphatically thumped Inter Milan 5-1 in the 2003/04 campaign.