Robinho scored twice and Kevin-Prince Boateng and Zlatan Ibrahimovic once each to lead seven-time European champion Milan to its first victory in eight games against an English Premier League team.
“We didn’t have the best of games but you have to give credit to Milan, they punished us on every occasion,” Arsenal goalkeeper Wojciech Szczesny said in a televised interview with ITV. “It’s a very disappointing day for us.”
Roman Shirokov scored in the 88th minute to give Zenit, making its first appearance in the round of 16 in Europe’s elite club competition, the win in Russia. It came one minute after Oscar Cardozo tied the score for two-time champion Benfica.
Arsenal and Benfica host the return matches in the two-game series March 6, with the winners advancing to the quarterfinals. Milan, one of three Italian teams remaining in the competition, last reached the final eight on its run to the title in 2007.
“We are not qualified yet,” Milan coach Massimiliano Allegri told UEFA’s website. “England is always a difficult place to play and we need to show another convincing display.”
Milan went in front in the 15th minute as Boateng took a pass off his chest on the edge of the area and fired a shot over Szczesny and in off the underside of the crossbar. The Italian league leader doubled its advantage in the 38th minute as Robinho headed in Ibrahimovic’s cross.
Henry’s Final Game
Arsenal brought on Thierry Henry, playing the final game of his loan spell from the New York Red Bulls, to start the second half. Milan struck again four minutes after the restart as Robinho, given space when defender Thomas Vermaelen slipped, put a shot inside the left post.
Arsenal’s closest effort came midway through the second half as Robin van Persie forced a diving save from goalkeeper Christian Abbiati. Ibrahimovic then closed the scoring with a 79th-minute penalty kick after being taken down by Johan Djourou. It was the Swedish striker’s fifth goal in as many games in the competition.
Arsenal had never previously lost by a four-goal margin in Europe. The Gunners twice fell to 4-1 away defeats in the Champions League, most recently to Barcelona in the 2010 quarterfinals, and were beaten 5-2 at home by Spartak Moscow in the 1982 UEFA Cup.
Deportivo La Coruna has the greatest comeback in the competition, beating Milan 4-0 at home after an opening 4-1 loss in Italy in the 2004 quarterfinals.
“Let’s be realistic, we don’t play in a dream world,” Arsenal manager Arsene Wenger said in comments on his team’s website. “We have to show a completely different performance and you never know. But, you have to say, realistically, we are out of the competition.”
In Russia, Zenit overcame a temperature of minus-10 degrees Celsius (14 Fahrenheit) and two errors by goalkeeper Yuri Zhevnov to hand Portuguese league leader Benfica its second loss in 36 games this season.
“That was a nervous match, a very emotional and passionate game,” Zenit coach Luciano Spalletti said on UEFA’s website. “My lads won it with their heart, though they also showed a lot of quality.”
Benfica took the lead in the 20th minute as Zhevnov pushed Cardozo’s free kick into the path of Maxi Pereira, who knocked it into the open net. Zenit tied the game seven minutes later as Shirokov volleyed in Tomas Hubocan’s cross.
Zenit took the lead in the 71st minute on a goal from Sergei Semak. Benfica tied it with three minutes remaining as Zhevnov failed to hold Nicolas Gaitan’s shot and Cardozo knocked in the rebound.
Zenit then won it one minute later as Pereira couldn’t control a cross into the Benfica area. Shirokov picked up the loose ball and put a shot past goalkeeper Artur.
“The tie is open and at our stadium, with our supporters, we can go through,” said Benfica coach Jorge Jesus. “We have every chance to correct this at home.”
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