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AC Milan's Champions League campaign ended with a draw against Feyenoord at the San Siro, resulting in their elimination from the knockout play-off round. Santiago Gimenez's goal after just 36 seconds, the fastest in this season's competition, briefly put Milan ahead on aggregate, wiping out Feyenoord's first-leg advantage, but they ultimately failed to secure the win needed to advance.
But Milan full-back Theo Hernandez was sent off in the 51st minute for two yellow cards and Feyenoord substitute Julian Carranza headed in the decisive 73rd-minute goal to seal a 2-1 aggregate success.
The last-16 draw, to be held on Friday, will decide whether the Dutch club face Inter Milan or Arsenal next month.
Seven-time European champions Milan had the perfect start with Gimenez's effort. Christian Pulisic's cross to the back post was nodded back into the danger zone by Malick Thiaw for the Mexico international to head home from close range for his sixth goal of the competition - five of which came in Feyenoord colours before he left them in the winter transfer window.
Sergio Conceicao's side pushed for the aggregate lead as Tijjani Reijnders and Joao Felix went close, before Hernandez's fierce strike cannoned off the upright in the 23rd minute.
Rafael Leao was denied by Timon Wellenreuther in the closing stages of the first half and the Feyenoord goalkeeper was also tested again early in the second half by Kyle Walker's low drive from the edge of the box.
The Dutch side, under interim manager Pascal Bosschaart, were then handed a boost when Frenchman Hernandez received a second booking for simulation six minutes after the restart.
Feyenoord capitalised on the numerical advantage as Carranza met Hugo Bueno's cross to plant a thumping header past Milan captain Mike Maignan and send his side through to the last 16 of the premier European competition for the first time since 1974.
However, they will be without Givairo Read for the last-16 tie as the right-back received a red card for violent conduct when tensions flared between the sides after the final whistle.
