Since November 3, 2010, when Real Madrid drew 2-2 against AC Milan during their visit to San Siro in the fourth match of the Champions League group stage, a classic European football matchup featuring the two most decorated teams in European Cup history has not taken place. The once-feared Madrid side visits a Santiago Bernabéu where they have won only once.

The 15 Champions League titles of Real Madrid and the 7 of AC Milan will come together on the Bernabéu pitch, totaling 22 European conquests in what is the most successful match in European football. This historic rivalry has recently been surpassed by Bayern Munich in terms of encounters against the European king.

Looking back over the 14 years since their last meetings, memorable clashes come to mind, such as the final won by Madrid in Brussels in 1958, or the Italian dominance over the “Quinta del Buitre,” preventing them from claiming glory.

Interestingly, it took Milan 53 years to achieve a victory at the Santiago Bernabéu. This span lasted from April 1956, when they lost 4-2 in the first leg of the semi-finals on their initial visit, to October 2009, the only date on which they triumphed in eight matches at Madrid’s temple. They won 3-2 during the group stage, with goals from Pirlo and a brace from Brazilian Pato, who scored the final goal in the 88th minute, nullifying efforts from Raúl González and Royston Drenthe.

This historic rivalry has shown alternating dominance across decades, resulting in an overall balance in their encounters in Europe’s most prestigious competition. In 15 Champions League matches, formerly the European Cup, Madrid and Milan have each claimed six victories, with three matches ending in draws. Madrid has scored 24 goals, while the Italians have netted 25.

During the 1980s, Milan became a nemesis for Real Madrid in Europe, with legends like Baresi, Maldini, Rijkaard, Gullit, Van Basten, and Carlo Ancelotti, the current Madrid coach who has brought great glory to the club, preventing the “Quinta del Buitre” from enhancing their legacy in the coveted European Cup.

In two consecutive seasons, Milan dashed Madrid's dreams, crushing them with a 5-0 defeat in the semi-finals and a 2-0 loss in the round of 16, pushing the “Seventh” title further from one of the club's best generations.

Since then, encounters have lost their significance, particularly the last meetings in 2009 and 2010, where they exchanged blows. Milan's first victory in Madrid (3-2) and a draw at San Siro (1-1) were followed by Madrid's comfortable win at the Bernabéu with early goals from Cristiano Ronaldo and Mesut Özil (2-0) and a late equalizer in Italy (2-2) from Pedro León, before José Mourinho secured passage to the knockout stages with two games to spare.