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Milan handed Los Blancos their second defeat of the Champions League campaign to pile pressure on Carlo Ancelotti.
Real Madrid's poor showing this season continued as they were soundly beaten 3-1 at home by Paulo Fonseca's AC Milan.
Real Madrid looked on the rise after Vinicius's penalty equalised Milan's opener, but Fonseca's men wrestled back control and with goals from Alvaro Morata and Tjjani Reijnders, they blew their hosts away.
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Key match details
Real Madrid's sluggish start proved costly as AC Milan seized the initiative, capitalising on a set-piece vulnerability inside 15 minutes. Christian Pulisic's corner found Malick Thiaw, who headed home at the near post.
The host roused and moments later, Vinicius earned a penalty after being fouled by Emerson Royal and subsequently converted with a cunning panenka-style spot-kick.
Despite Real's expected dominance, Paulo Fonseca's Milan refused to yield and soon regained the lead. Rafael Leao’s attempt was saved by Lunin, but Alvaro Morata pounced on the rebound to score against his former club.
Milan continued to exploit their hosts' defensive lapses upon resumption while nullifying their creative threats. Lunin's acrobatic save denied Leao's header shortly after the restart, but Milan's relentless pressure ultimately told.
A slick team move culminated in Leao's pinpoint cross-finding Reijnders, who slotted home through Lunin's legs to seal a historic victory.
Antonio Rudiger's late strike was ruled out for offside, capping a dismal night for Real Madrid, who now face an uphill battle to secure automatic passage to the Champions League last 16.
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