Arsenal will face last season's champions of Europe, AC Milan, in the first knockout round of the Champions League. The Gunners, who finished second in their group, arguably drew the toughest team in the competition.
The other teams who Arsenal could have been matched with were Barcelona, Real Madrid, Inter Milan, and Porto.
Arsenal will take on the holders at home on Wednesday February 20th, and at the San Siro on Tuesday March 4th, as Arsene Wenger's youngsters square up against one of Europe's biggest powers.
Last season, Arsenal was knocked out in this round after losing to PSV Eindhoven in a disappointing show. The Gunners will be hoping they show more class against a Milan side that is flourishing in Europe but stuttering in the Serie A.
Arsene Wenger was optimistic despite the tough draw.
"The draw is interesting and exciting," he said. "But do I believe that we can do it? Yes. AC can be really average in the championship but can raise their game on big occasions. That is something that is really surprising. They look invincible in Europe but beatable in Italy. They had an average championship last year and have again this year. We have to analyze what gets them there on the special occasion.
"Still I believe we can knock AC Milan out and why should we reduce our ambitions? As well, I believe my squad can improve until the end of February and beginning of March.
"What I would like my squad to do now is to focus on the Premier League and be in a comfortable position when we play Milan, so that, at that time, we can focus completely on the Champions League during these 15 days."