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In the 2007--08 Champions League final on 21 May against league rivals Chelsea, Ronaldo scored the opening goal after 26 minutes, which was negated by a Chelsea equaliser in the 45th minute as the match ended 1--1 after extra time. His misfire in the penalty shoot-out put Chelsea in position to win the trophy, but John Terry shot wide right after slipping on the pitch surface, and Manchester United emerged victorious 6--5 on penalties. Ronaldo was named the UEFA Fans' Man of the Match,[47] and wrapped up the campaign with a career-high 42 goals in all competitions, falling four short of Denis Law's team-record mark of 46 in the 1963--64 season.
Ronaldo and Manchester United against Albert Riera and rivals Liverpool.
On 5 June 2008, Sky Sports reported that Ronaldo had expressed an interest in moving to Real Madrid if they offered him the same amount of money the team had allegedly promised him earlier in the year.[48] Manchester United filed a tampering complaint with FIFA on 9 June over Madrid's alleged pursuit of Ronaldo, but FIFA declined to take any action.[49][50] Speculation that a transfer would happen continued until 6 August, when Ronaldo confirmed that he would stay at United for at least another year.[51]
Ronaldo underwent ankle surgery at the Academic Medical Center in Amsterdam on 7 July.[52] He returned to action on 17 September in United's UEFA Champions League goalless group-stage draw with Villarreal as a substitute for Park Ji-Sung,[53] and scored his first overall goal of the season in a 3--1 League Cup third round win over Middlesbrough on 24 September.
In a 5--0 win over Stoke City on 15 November 2008, Ronaldo scored his 100th and 101st goals in all competitions for Manchester United, both from free kicks.[54] The goals also meant that Ronaldo had now scored against each of the other 19 teams in the Premier League at the time.[55] On 2 December, Ronaldo became Manchester United's first Ballon d'Or recipient since George Best in 1968. He finished with 446 points, 165 ahead of runner-up Lionel Messi.[56] He was awarded the Silver Ball after finishing with two goals as United won the Club World Cup on 19 December.[57]
On 8 January 2009, Ronaldo was uninjured in a single-car accident in which he wrote off his Ferrari 599 GTB Fiorano in a tunnel along the A538 near Manchester Airport. A breathalyser test he gave to police officers at the scene was negative, and he attended training later that morning.[58] Four days later, he became the first Premier League player ever to be named the FIFA World Player of the Year, in addition to being the first Portuguese player to win the award since Luís Figo in 2001.[59]
Ronaldo scored his first Champions League goal of the season, and first since the final against Chelsea, in a 2--0 victory over Internazionale that sent United into the quarter-finals.[60] In the second leg against Porto, Ronaldo scored a 40-yard game-winning goal as United advanced to the semi-finals. He later called it the best goal he had ever scored.[61][62] Ronaldo participated in his second consecutive Champions League final, but made little impact in United's 2--0 loss to Barcelona. He finished with 53 appearances in all competitions, which was four higher than the previous year, but scored sixteen fewer goals (26) than his career-best total of 42 from the previous season.
On 11 June, Manchester United accepted an unconditional offer of £80 million from Real Madrid for Ronaldo after it was revealed that he again had expressed his desire to leave the club.[63] It was confirmed by a representative of the Glazer family that the sale was fully condoned by Ferguson.[64] When Ronaldo had eventually completed his transfer to Real, he expressed his gratitude towards Ferguson for helping him develop as a player, saying, "He's been my father in sport, one of the most important factors and most influential in my career.