Although Milan qualified for the first Champions League games of the 1950s, they had yet to leave their mark. Their peak attempt at winning the “Cup with Big Ears” came really close in the 1957-1958 tournament. Leading up to that season there were some really hard knocks, as Milan reached semi-finals in the 1955-56 (the first Champions League season), and lost to Real Madrid 5-4. The 1956-57 Champions League season did not see Milan at all, as Fiorentina represented the Italian section of europe.
In their attempt at Champions League victory in the 1957-58 season, Milan had some interesting results, where they went on to draw on aggregate 6-6 against Rapid Wein, which lead to a third (playoff) match to determine the absolute winner. The result of the playoff was a 4-2 Milan victory. Their next game lead to a 6-1 aggregate victory against the Rangers, then a 5-2 aggregate victory against Borussia Dortmund in the Quarter-Finals, and a 2-5 aggregate victory against Manchester United in the Semi-Finals.
The Final against Real Madrid was a rough game for both fans, as the game remained 0-0 for the entire first half. The first to break the ice was Milan in the second half, where Schiaffino scored in the 59th minute, but only to be equalized by Madrid’s Di Stefano soon after. Another Rossoneri goal in the 77th minute by Grillo brought the score to 2-1. It certainly looked to be a game without end, and without certainly for victory on either side. In the 79th minute, Real’s striker Rial, put in a goal to equalize the game 2-2 until the 90th minute. This meant extra time. To the dismay of the Rossoneri, a goal was scored in the 107th minute by Madrid’s Gento, leaving the game with a 3-2 final score, and earning Real Madrid’s 3rd (and consecutive) straight Champions League victory. This evidently left Madrid with an early start in their legacy for the Champions League cup, but AC Milan had yet to leave their mark and in a very big way, in the years to come.
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