From 1987 until 1992, Ancelotti played for Milan, and was a key part of the successful squad that won the Serie A title in 1988, consecutive European Cups in 1989 and 1990, two European Super Cups, two Intercontinental Cups and a Supercoppa Italiana under manager Arrigo Sacchi. During this time, Milan played with one of their finest teams ever assembled in that decade under the financial backing of club president Silvio Berlusconi, with Paolo Maldini, Franco Baresi, Mauro Tassotti and Alessandro Costacurta as defenders; Frank Rijkaard, Ruud Gullit and Roberto Donadoni as midfielders; and Marco van Basten upfront. One of Ancelotti's most memorable moments with Milan was when he received a pass from Ruud Gullit, dribbled around two Real Madrid players and netted a powerful long-range shot during the "Rossoneri's" 5–0 thrashing of Real Madrid in the 1989 European Cup semi-finals. He went on to play all 90 minutes in Milan's 4–0 dismantling of Steaua București in the final.