Despite having dominated large parts of the first leg in the San Siro last month, AC Milan travel to Atletico Madrid this evening up against a one-goal deficit.
As a result, the seven-time European champions need to win in the Spanish capital or they will exit the Champions League for another campaign.
The Rossoneri's three previous victories in Spain would be enough to at least force the last-16 tie into extra time tonight, and below Sports Mole reviews each of those encounters.
1. Deportivo La Coruna 0-1 Milan, 2000
Hosting Deportivo had not lost a European encounter at the Estadio Riazor in almost three years prior to Milan's visit, but the Red and Blacks returned to Italy with all three points from this second group stage encounter. There was early drama when Milan goalkeeper Christian Abbiati was struck by a flag pole thrown from the crowd, although after medical attention, he was able to continue. The match was eventually won thanks to a strike from future Norwich City right-back Thomas Helveg, who scored only his second goal for Milan with a powerful drive.
2. Deportivo La Coruna 0-4 Milan, 2002
Milan were drawn in the same group as Deportivo again two seasons later, but while they recorded a narrow win from their previous trip to Northern Spain, this one was more emphatic. Current Milan head coach Clarence Seedorf broke the deadlock with a curling effort from the edge of the area, before Filippo Inzaghi took centre stage. The Italian frontman made it 2-0 before the break, while he added two more goals after the restart to complete his hat-trick.
3. Real Madrid 2-3 Milan, 2009
For the first hour of this group encounter, there was very little to talk about. A huge error from Milan goalkeeper Dida allowed Raul to give the hosts an early lead, but it wasn't until a long-range equaliser from Andrea Pirlo that the match burst into life. Alexandre Pato then quickly put the Italians in front, before Royston Drenthe replied for the hosts. Then, just as it appeared that the spoils would be shared, Pato volleyed in from close range two minutes from time to send Milan top of Group C.
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