Milan
Silvio Berlusconi signed Gullit for A.C. Milan in 1987, paying the then world record transfer fee of ƒ18 million (£6 million) as a replacement for Ray Wilkins. Among his teammates at that club were compatriots Marco van Basten and Frank Rijkaard, along with Paolo Maldini and Franco Baresi. Gullit's exploits with first PSV and then Milan helped him win the European Footballer of the Year award in 1987 which he dedicated to Nelson Mandela.
When he arrived at Milan, Gullit initially struggled to settle as he spoke no Italian and was unused to living in a foreign country. However, Gullit's first season at Milan saw the club win Scudetto for the first time in 9 years, under coach Arrigo Sacchi. He was initially used on the right of an attacking trio alongside Van Basten and Pietro Virdis, but after an injury to Van Basten it was changed to a front two. The following season Milan built on their domestic success by adding the European Cup to their list of honours. Their scintillating 5–0 demolition of Real Madrid in the semi-final second leg came at a cost, as Gullit suffered an injury and required surgery to be fit in time for the final. That performance was followed by a 4–0 victory over Steaua Bucharest in the 1989 final with Gullit scoring two crucial goals. The following year Milan retained the trophy as they defeated Benfica in the 1990 final. However, serious injuries sustained to the ligaments of his right knee limited Gullit's playing time and he managed just 2 domestic games in the 1989–90 season before appearing in the cup final.
In 1990–91 Milan's pursuit of a third consecutive European Cup was cut short by Olympique de Marseille at the quarter-final stage. Having drawn the first leg at the San Siro, Milan trailed to a Chris Waddle goal with little time remaining when the floodlights went out. After a short delay the lighting was restored, but Milan had returned to their dressing room and refused to return to complete the game. UEFA awarded Marseille a 3–0 victory and expelled Milan from all European competitions for the following season.
While Milan continued their domestic dominance by winning Serie A in both 1991–92 (a season in which they went undefeated) and 1992–93, Gullit's position was an increasingly peripheral one. This was demonstrated by his omission from the UEFA Champions League Final 1993 final as under the UEFA rules clubs were only allowed to field 3 foreigners.
Read more about this topic: Ruud Gullit, Club Career