Arsenal may be having a relatively difficult domestic campaign, but their European form has been the envy of teams far higher up the Premier League table. Having cruised though Group F, securing top spot before the final game, Arsenal were rewarded with drawing a second-place team - only to end up with defending Serie A champions AC Milan.
It's an unfortunate draw, certainly, but as Tottenham Hotspur showed last season, Milan are hardly the all-conquering force they once were, and the Gunners can probably manage to get past them this year. In order to do that, they'll have to get at least a draw or an away goal at the San Siro. The good news, of course, is that Arsenal's primary weakness - their fullbacks - is rather countered by Milan offering very little on the flanks, a problem that's compounded by Arsenal having the likes of Alex Oxlade-Chamberlain on the wings.
If exploiting Milan's lack of width sounds like a familiar gambit, it's exactly what Harry Redknapp did to them at this stage last season. There's no reason it can't work again for Arsenal, who in Robin van Persie have a player responsible for making the most of any chances the visitors will get, despite going up against Thiago Silva and Alessandro Nesta in a strong Milan centre back pairing.
If the wings are Arsenal territory, the middle of the pitch is probably a different story. Once upon a time, the Gunners would have expected to control the midfield in virtually every game they contested, but with Cesc Fabregas moving on and Jack Wilshere still injured, they probably don't have the quality to deal with Milan's centre, which is dominated by Mark van Bommel and should be bolstered by the supposed return from injury of Kevin-Prince Boateng.
If the Scudetto holders can dominate possession, things will get dicey for an injury-plagued Arsenal back line. Per Mertesacker was a casualty of last weekend's win against Sunderland, which means Thomas Vermaelen will move into the middle, opening up a Gael Clichy-shaped hole at left back that will actually be filled by Francis Coquellin. The defence faces a mean task in containing the likes of Robinho and Zlatan Ibrahimovic - no matter what the British press may think of them, they're both more than capable of taking the game by the scruff of its neck and causing the Gunners major difficulty.
It's very easy to see Milan scoring, but Arsenal are more than capable of getting a goal on the break as well. This looks like a 1-1 draw to me, a result that would put the Gunners in a good position to repeat the feat of their North London rivals in knocking out the Rossoneri.
AC Milan vs. Arsenal
Game Date/Time: Wednesday, February 14, 2:45 p.m. ET, 8:45 p.m. CET.
Venue: San Siro, Milan, Italy.
TV: FSC (USA), Sportsnet Regional (Canada)
Projected Lineups
AC Milan (4-3-1-2): Christian Abiati; Gianluca Zambrotta, Thiago Silva, Alessandro Nesta, Ignzaio Abate; Antonio Nocerino, Mark van Bommel, Urby Emanuelson; Kevin-Prince Boateng; Robinho, Zlatan Ibrahimovic.
Arsenal (4-3-3): Wojciech Szczesny; Francis Coquelin, Thomas Vermaelen, Laurent Koscielny, Bacary Sagna; Alex Song, Mikel Arteta, Aaron Ramsey; Alex Oxlade-Chamberlain, Robin van Persie, Theo Walcott.
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