The Italian side dominated proceedings at San Siro and all but sealed progression to the next round of the Champions League thanks to the brilliance of its attacking trio.
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Arsenal faces elimination from the Champions League at the hands of AC Milan after falling to a comprehensive 4-0 defeat at San Siro.
After Kevin-Prince Boateng had opened the scoring with a stunning volley, Robinho scored twice to hand the home side a commanding lead before Zlatan Ibrahimovic added a gloss to the scoreline.
While there is no doubt it was aided by Arsenal's utter inability to exert any sort of control in midfield, Milan thoroughly deserve its three-goal cushion as the tie heads back to London having delivered a stylish performance orchestrated by Ibrahimovic.
Kieran Gibbs returned at left back for the Gunners, allowing Thomas Vermaelen to shift into central defense alongside Laurent Koscielny. Arsene Wenger opted to select Tomas Rosicky in midfield ahead of Alex Oxlade-Chamberlain.
Former Tottenham midfielder Boateng recovered from injury in time to face Spurs' Premier League rivals, with Ibrahimovic and Mark van Bommel immediately restored to the starting XI following suspension. Alessandro Nesta and Alexandre Pato, who have both recently resumed full training, were included among the substitutes.
The attacking trio of Boateng, Ibrahimovic and Robinho immediately looked a threat. After Clarence Seedorf was forced off due to injury early on, Ibrahimovic beautifully controlled a pass into the path of his replacement, Urby Emanuelson, but the Netherlands midfielder skewed his shot from inside the box over the crossbar.
It did not take long for Boateng to do significantly better. Picked out by Alberto Nocerino's chipped pass, the Ghana midfielder engineered a brilliant volley from the right-hand side of the penalty area that hit the crossbar on its way in.
Arsenal seemed to have survived the resulting Milan onslaught, with Nocerino shooting over the crossbar and Ibrahimovic perhaps unfortunate to be penalized for a foul on Vermaelen. The Belgium defender, normally so strong for the Gunners, was not enjoying his best evening and was bailed out by defensive partner Koscielny when he was robbed of the ball by Robinho on the halfway line.
There was little either of them could do when Ibrahimovic broke away from what looked like an offside position down the left-hand side. His influence in the match growing, the 30-year-old nudged the ball past Sagna and stood the ball up for the arriving Robinho, who headed beyond Wojciech Szczesny.
Only a desperate challenge from Sagna prevented Ibrahimovic from converting with a diving header from close range as Milan ended the half very much in the ascendancy. The former Barcelona striker then did brilliantly to spin away from substitute Johan Djourou and play in Boateng, but he shot wide.
Thierry Henry, playing his last game for Arsenal before the end of his loan spell, was introduced in place of Theo Walcott at the break. If Wenger was hoping for any kind of fairytale farewell, he was brought back to reality minutes after the restart when Robinho, taking advantage of Vermaelen's slip, latched on to Ibrahimovic's pass across the edge of the box and fired past Szczesny from 20 yards.
Milan began to enjoy itself with the security of a three-goal cushion, Philippe Mexes feeling confident enough to dribble ambitiously out of defence on more than one occasion, until van Persie fired them a warning signal after 65 minutes. The Netherlands forward met Henry's flick with a sweetly struck volley that Christian Abbiati did very well to turn around the post.
Massimiliano Allegri was quick to react, introducing an experienced head in the form of Massimo Ambrosini to shore up the Milan midfield as Arsenal began to enjoy more of the ball.
Ibrahimovic has taken plenty of criticism during his career for his perceived underachievement in these types of matches, but he was magnificent here and created himself a deserved goal as the game drew to a close.
Drawing a clumsy challenge from the sorry Djourou in the penalty area after some producing some typically elegant close control, Ibrahimovic coolly converted from the spot to rub salt into the Arsenal wounds.