Arsenal always seem to draw a tough opponent in the Round of 16 in Champions League, and this season is no different as the Gunners will meet Serie A powerhouse AC Milan in mid-February.

Last season, Arsenal faced Barcelona, and defeated the champions in the first leg at Emirates, but then were eliminated at Camp Nou in a controversial match. In 2009-2010, the Gunners drew FC Porto, who defeated Arsenal in the flrst leg, but Arsene Wenger's squad would later advance in a 5-0 victory at Emirates.

In 2008-2009, Arsenal needed penalty kicks to escape past Francesco Totti-led Roma. Prior to that, Arsenal faced AC Milan in another tight battle.

Indeed, Wenger probably saw the clubs Arsenal could have faced in the Round of 16, and shook his head. AC Milan pose a far more difficult challenge than Zenit St. Petersburg, Lyon, and CSKA Moscow. Many would argue that of all the clubs that finished second in the group stages, that AC Milan have the most talent-rich roster.

Massimiliano Allegri's squad is just two points out of first place in the Serie A table, and gave Barcelona two very competitive games in group play.

With the January transfer period looming, Wenger may need to bolster his squad if he expects to make a legitimate run at the title. The club lacks defenders with Andre Santos, Bacary Sagna, and Kieran Gibbs all sidelined for an extended period. AC Milan have some notable forwards to contain, which include Alexandre Pato, Robinho, and Zlatan Ibrahimovic.

Arsenal are going to find it just as tough against Milan, said Glenn Hoddle, according to ESPN. Arsenal have been conceding too many goals lately and I don't see how they can stop conceding against the top sides like Milan. For many years now Arsenal have been one of the best passing teams, retaining possession, as good as anyone in Europe apart from Barcelona, but now they have deficiencies in defense that could cost them dear.