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Arsenal came within a goal of producing an unprecedented Champions League comeback but just came up short as they beat AC Milan 3-0.
First half goals from Laurent Koscielny, Tomas Rosicky and Robin van Persie set the Gunners on their way to an astonishing recovery but Milan were able to regroup at the interval and held out to secure progression to the quarter final by an aggregate score of 4-3.
Milan's performance during the first 45 minutes was woeful, their frequent defensive errors allowing Arsenal back into the tie, but Massimiliano Allegri successfully reorganised his troops at the break and the Italians clung on.
Arsenal lined up in a more attacking style than usual due not only to the four-goal deficit they faced but also as a result of the absence of midfielders Mikel Arteta, Aaron Ramsey and Abou Diaby. Alex Oxlade-Chamberlain and Gervinho joined Theo Walcott in support of van Persie.
Milan made midfield changes of their own, with Kevin-Prince Boateng and Clarence Seedorf injured. Urby Emanuelson and Stephan El Shaarawy started alongside Antonio Nocerino and Mark van Bommel.
There are few more adept midfield anchormen in European football than van Bommel, but the Dutchman's poor start to this game handed the Gunners hope. After receiving an early booking for a foul on Rosicky, van Bommel failed to stick to Koscielny as Oxlade-Chamberlain whipped in a corner from the Arsenal left, allowing the Frenchman to head home at the near post after seven minutes.
If Arsenal were pleased to see van Bommel carded early on, the decisions of the somewhat over-zealous referee soon became an annoyance. Bacary Sagna and Kieran Gibbs saw yellow as Arsene Wenger's team continued to press, with van Persie forcing Christian Abbiati into two good saves inside the opening 20 minutes.
Milan seemed to be slowing the tempo of the game down but Arsenal continued to expose the Serie A side's defence and revived the tie with two goals before half-time. First, Walcott raced down the right wing and fired a low pass across goal that was poorly cleared by an off-balance Thiago Silva straight into the feet of Rosicky, who calmly guided the ball beyond Abbiati.
Djamel Mesbah, in the absence of Luca Antonini, was enduring a torrid time at left-back and Arsenal were to take advantage of the Algerian in the build-up to their third goal. Oxlade-Chamberlain broke into the box past Nocerino only to find his path blocked by Mesbah, resulting in a penalty kick dispatched with aplomb by van Persie.
All the focus was on Arsenal's search for a fourth goal but they might have had their hopes of progression put to bed if not for goalkeeper Wojciech Szczesny. First, the Poland international raced off his line to sufficiently narrow the angle and force El Shaarawy to shoot wide, as the Emirates Stadium held its collective breath, and he was alert enough to repeat the trick on Zlatan Ibrahimovic after the break, this time saving at the feet of the Swede.
Szczesny's efforts were topped by Abbiati as the game approached the hour mark. Rosicky led a break into the Milan half and picked out Gervinho to his left. Abbiati did very well to stop the Ivorian's shot after it had taken a deflection and then proceeded to deny van Persie, who had pounced on the rebound, from point blank range.
Szczesny was to make an equally important save 15 minutes later, but knew less about it. Substitute Alberto Aquilani slid a pass across the Arsenal box towards the back post and with half the goal to aim at, Nocerino poked his effort tamely back into the legs of the 21-year-old goalkeeper.
Arsenal's second half display was less dynamic than their first, and Milan's perhaps less error-strewn. Rosicky used the ball well but struggled to exert a consistent influence over the game, as did Gervinho, while Walcott displayed his more frustrating side after a positive first 45 minutes. Marouane Chamakh joined van Persie in attack but it was a creator, not a goalscorer, that the Gunners lacked.
A dreadful Alex Song pass as Arsenal attacked for the final time summed up a disappointing second half that left Wenger's players dejected at the final whistle despite such a credible performance and victory.
