Real's 'saddest night' against Milan: When Ancelotti himself was part of the offside trap

The legendary coach was a player for the Rossoneri when they beat Real Madrid 5-0 in the 1989 European Cup semi-final

The Italian played the full 90 minutes in one of Real's darkest nights in European competition

Carlo Ancelotti has a long and distinguished history with Real Madrid, having managed the club to three Champions League titles and a La Liga crown. However, there was a time when he was on the other side of the rivalry, playing for AC Milan in a famous 5-0 win over Real Madrid in the 1989 European Cup semi-final. That night, Ancelotti played the full 90 minutes as Milan tore Real Madrid apart, with Marco van Basten scoring a hat-trick. It was a night that Ancelotti would never forget, and it remains one of Real Madrid's darkest nights in European competition.

Ancelotti was a key player for Milan in the late 1980s and early 1990s, winning two Serie A titles and two European Cups. He was a versatile midfielder who could play in a variety of positions, and he was known for his intelligence, passing ability and eye for goal. In the 1989 European Cup semi-final against Real Madrid, Ancelotti played in a central midfield role, alongside Ruud Gullit and Frank Rijkaard. Milan were the overwhelming favorites going into the match, and they made their superiority count from the start. Van Basten opened the scoring in the 18th minute, and Milan were 3-0 up by half-time. Real Madrid never recovered, and Milan went on to win the match 5-0. It was a humiliating defeat for Real Madrid, and it is still remembered as one of the worst nights in the club's history.

For Ancelotti, the match was a bittersweet experience. He was delighted to have played a part in such a famous victory, but he also felt sorry for his former club. "It was a strange feeling," he said after the match. "I was happy to have won, but I also felt sad for Real Madrid. They are a great club, and they didn't deserve to lose like that." Ancelotti's feelings are understandable. He had spent many years at Real Madrid, and he still had a lot of affection for the club. However, he was also a professional, and he was determined to help Milan win the match. In the end, he did both. He helped Milan to a famous victory, and he also showed his respect for his former club.