5 times European giants were humiliated in European club football

#3 AC Milan (5 – 0) Real Madrid, San Siro (Milan), Semi-Finals, 1988-89

(First leg tied 1-1)

The AC Milan team had several stars who would go on to have impressive careers

If there was any doubt of the changing times in European football and its dominant forces, this match established that fact, loud and clear. Real Madrid, the most successful club in continental championships for nearly three and a half decades, were humbled by a rejuvenated Milan side that would go on to be one of the most feared sides for a large part of the next decade.

Milan carried an advantage going into the second leg having come away with an away goal in Madrid, courtesy Marco Van Basten, and the first-leg ended 1-1. What followed in Milan in the second leg is a score-line many find difficult to believe even today. Unlike Italian sides of the past, Arrigo Sacchi’s men believed in not just outscoring opponents, but scoring a flurry of goals. The Milan side also had a lot of attacking outlets and goal-scoring options.

This was exemplified by Milan’s 5-0 thrashing of Real in the second leg at home, with goals coming from 5 different goal scorers. Each member of the Dutch Trio of Death: Marco Van Basten, Frank Rijkaard and Ruud Gullit, had their names on the score sheet, and their goals were flanked on either side by coaches of the future, Carlo Ancelotti and Roberto Donadoni.

Milan would go on win the title with another 4-0 drubbing of Steaua Bucharest, and Real would go down in the record books humbled and embarrassed.