On 18 January 2007, it was reported that Ronaldo agreed terms with Milan for a transfer of about €7.5 million.[7] Ronaldo was forced to pay for the remaining period on his contract which tied him to Real Madrid, only because the latter did not agree to release him, while Milan were not ready to pay such a sum. On Thursday, January 25 Ronaldo flew from Madrid to Milan to watch Milan in a cup tie against Roma. Statements on the club's website said that Ronaldo was in Milan for a medical, and that a meeting had been arranged for Monday with Real Madrid officials to discuss and finalize his transfer to Milan. On 26 January, Ronaldo successfully completed his medical tests at the Milanello training complex under the supervision of club doctors, and the transfer completed on January 30[8] and got the jersey number 99. He made his debut as a substitute for Milan on 11 February 2007, during the 2-1 victory over Livorno. The next game at Siena on 17 February 2007, Ronaldo scored twice and assisted on a third goal in his first start for Milan as they won an exciting game 4-3. In his first season at Milan, Ronaldo scored 7 goals in 14 appearances.[5]
After his move to Milan, Ronaldo joined the list of the few players to have played for both Internazionale and Milan in the Milan Derby and is the only player to have scored for both sides in the derby game (for Inter in the 98/99 season and for Milan in the 06/07 season). Ronaldo is also one of the few players to have started for Real Madrid and Barcelona, which also boasts a heated rivalry. However, Ronaldo has never transferred directly between the teams in the derby. Ronaldo only played 300-plus minutes for Milan in his single season at Milan due to recurring injury problems and weight issues. Ronaldo's only goals in the 2007/2008 season, besides his goal against Lecce in pre-season, came in a 5-2 victory against Napoli at the San Siro, where he scored an emotional brace. It was also the first time Milan's much hyped attacking trio of Kaká, Alexandre Pato and Ronaldo, known as Ka-Pa-Ro played together. In total he scored 9 goals in 20 appearances for Milan.
Despite tremendous success over the past decade, Ronaldo has never won the UEFA Champions League in his club career. During the 2006-07 season, though Milan won the 2006-07 title, Ronaldo was cup-tied with Madrid and ineligible to take part. The closest that he has been was in 2003 when he helped Real Madrid to the semi-finals, in which they lost to Juventus.
On 13 February 2008, Ronaldo suffered a severe season-ending knee injury while jumping for a cross in Milan's 1-1 draw with Livorno, and was stretchered off and taken to a hospital. Milan confirmed after the match that Ronaldo had ruptured the kneecap ligament in his left knee. It marked the third such occurrence of this injury, which he suffered twice to his right knee in 1998 and 2000.[9] He was released by Milan at the end of the season, as his contract expired and was not renewed.
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