2002–2005: Ballon d'Or win and La Liga championship
Having signed for Real Madrid for €46 million, his jersey sales broke all records on the first day. Ronaldo was part of the Galácticos era of global stars signed by the club every summer, which included Zinedine Zidane, Luís Figo, Roberto Carlos and David Beckham. He was sidelined through injury until October 2002 which added to the fans anticipation. Ronaldo scored twice on his debut against Alavés, the first 61 seconds after coming on, and he received a standing ovation at the Santiago Bernabéu as he left the field. That same reception was observed at the final game of the season against Athletic Bilbao, where Ronaldo scored to finish his first season with 23 league goals and seal La Liga title for 2003. He also won an Intercontinental Cup in 2002 and Spanish Super Cup in 2003, scoring in both finals.
Ronaldo taking a shot for Real Madrid, 2 March 2005
In the second leg of Real Madrid's Champions League quarter-final, Ronaldo scored a hat-trick against Manchester United at Old Trafford, knocking the English team out of the competition. Ronaldo was substituted on 80 minutes and was given a standing ovation from both sets of fans. Reflecting on the ovation given to him from the opposition's fans, Ronaldo stated, "For me it remains a very beautiful, very special moment." He scored in a 2–1 home win over Juventus in the first leg of the Champions League semi-finals, but injury crucially kept him out of most of the second leg defeat where Real were eliminated.
In the 2003–04 season, Madrid were on track to win the treble, until Ronaldo was injured towards the end of the season; they subsequently lost the Copa del Rey final, were knocked out of the UEFA Champions League quarter-finals to AS Monaco, and suffered a league form breakdown. During that second season at the club, Ronaldo scored one of the fastest goals in the club's history when he netted after 15 seconds in a league match against Atlético Madrid at the Bernabéu on 3 December 2003. Three days later he helped to ensure Real's first league victory over Barcelona at the Nou Camp in 20 years when he scored the second goal in a 2–1 victory over his former club. He finished the season as La Liga's top scorer with 25 goals and received the Pichichi Trophy for a second time, despite Madrid losing the league title to Valencia.
2005–2007: Final two seasons
"He [Ronaldo] was more talented [than Cristiano Ronaldo] and if he took care of himself like the Portuguese does, his performances would have been even more incredible."
In his final two seasons at Real Madrid, Ronaldo missed a number of games with injuries and weight issues, and with the acquisition of Ruud van Nistelrooy in 2006, he grew further out of favour with the manager Fabio Capello. Speaking in 2017 on Ronaldo's weight issues and lack of fitness at Madrid, in addition to his ability, Capello summed up the conflicting emotions he has with the Brazilian, "the most difficult player to handle was the best I coached: Ronaldo, il Fenomeno." In four and a half seasons at the club, Ronaldo scored over a century of goals, becoming the fifth foreigner at Madrid to achieve the feat after Argentine Alfredo Di Stéfano, Hungarian Ferenc Puskás, Mexican Hugo Sánchez and Chilean Iván Zamorano. Although the knee injuries before 2002 meant he "was robbed of the explosiveness of his early years" by the time he signed for Real Madrid, Ronaldo was named by Marca as a member of the "Best foreign eleven in Real Madrid's history".
While past his 1990s prime, Ronaldo still drew praise from his Madrid colleagues, with Zidane stating, "Without hesitation, Ronaldo is the best player I ever played with or against. He had such an ease with the ball. Every day I trained with him, I saw something different, something new, something beautiful." Michael Owen, who joined Madrid in 2004, acknowledged that he never got the chance to play with Ronaldo in his prime when "he had absolute blistering speed and strength, mesmerizing foot speed, he was just a blur, he'd be that fast", before adding, "even in training, he showed more than enough to convince me that I would have loved to play with him at his peak." Teammates for six months, Van Nistelrooy said, "Ronaldo was the best natural talent I ever played with. His innate ability went beyond anything that I'd ever seen or played alongside."
Ronaldo's Inter Milan away jersey (left) and A.C. Milan away jersey (right) in the San Siro museum. He played for Inter from 1997 to 2002, and A.C. Milan from 2007 to 2008.
On 18 January 2007, it was reported that Ronaldo agreed terms with A.C. Milan for a transfer of €8.05 million. Departing Real Madrid having been the club's leading goalscorer for all of his four full seasons, Ronaldo thanked everyone except Capello, "I would like to thank the fans who've supported me all the time and thank all the teammates that I've had here and all the coaches I've had – except one". Capello, who dropped him due to weight issues, commented, "I wish him the best of luck in doing what he used to do which is being a great player." On 25 January, Ronaldo flew from Madrid to Milan, with statements on the club's website stating Ronaldo was in Milan for a medical, and that a meeting had been arranged with Real Madrid officials to discuss and finalize his transfer to the Milanese club. On 26 January, Ronaldo successfully completed his medical tests at the Milanello training complex under the supervision of club doctors, and the transfer was completed on 30 January. Wearing the number 99 jersey, he made his debut as a substitute on 11 February 2007 in the 2–1 victory over Livorno. The next game at Siena, on 17 February, Ronaldo scored twice and assisted on a third goal in his first start for Milan, as they won 4–3. In his first season, Ronaldo scored seven goals in 14 appearances.
Ineligible to play having signed for the club mid season, Ronaldo (standing sixth from left) celebrated the 2007 UEFA Champions League triumph with his A.C. Milan teammates.
After his move to Milan, Ronaldo joined the list of the few players to have played for both Inter Milan and A.C. Milan in the Derby della Madonnina, and is one of few players to have scored for both rival teams in the Milan derby game (for Inter in the 1998–99 season and for A.C. Milan in the 2006–07 season), the others being players such as Giuseppe Meazza, Zlatan Ibrahimović, Enrico Candiani and Aldo Cevenini. Ronaldo is also one of the few players to have started for Real Madrid and FC Barcelona, which also boasts a heated rivalry. Ronaldo, however, has never transferred directly between rival clubs. Ronaldo only played 300-plus minutes in his second season at Milan due to recurring injury problems and weight issues. Ronaldo's only goals in the 2007–08 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 double. 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.
Despite tremendous success over the past decade, Ronaldo never won the UEFA Champions League in his club career. In 2019, FourFourTwo magazine named him the best player never to win the competition; in 2020, Sky Sports ranked him the second–best player (after Diego Maradona) never to win the Champions League or European Cup. Ronaldo stated, "I live football with a passion that doesn't give me any peace for not winning the Champions League – it's a trophy everyone would love to win." In 2011, Paul Wilson wrote in The Guardian, "Ronaldo was unlucky in his timing or his choice of club – for there is no doubt that at his very best he would have walked into any club in the world." 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 came to Champions League success 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 1–1 draw with Livorno, and was stretchered off and taken to a hospital. The club 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 1999 and 2000. Teammate Clarence Seedorf stated, "My heart stopped beating because it was like watching a repeat of the injury he suffered playing for Inter Milan against Lazio [in 2000]. His reaction was the same." Silvio Berlusconi told Italy's RAI TV, "He fears for his career. I called him last evening and told him to believe in himself. He has enormous physical potential." Ronaldo was released by Milan at the end of the season, as his contract expired and was not renewed.
2009–2010: Paulistão and Copa do Brasil
Ronaldo during his Corinthians unveiling in 2009, with Brazil president Lula handing him the jersey
Ronaldo trained with Rio de Janeiro based Brazilian club Flamengo during his recovery from knee surgery, and the club's board of directors said that the doors were open for him to join. On 9 December, however, Ronaldo signed a one-year deal with Flamengo's league rival Corinthians. The announcement received much publicity in the Brazilian press about his choice of Corinthians over Flamengo, since Ronaldo publicly declared himself a Flamengo fan. Rio-based sports newspaper Lance! called Ronaldo a "phenomenal traitor", and some angry fans burned Ronaldo shirts outside the Flamengo headquarters. Ronaldo responded that playing for Corinthians was the only option open to him. "I understand perfectly, I'm openly a Flamengo fan. But I was training with Flamengo for four months and didn't receive any offer. Corinthians made an offer that will let me continue my career."
Ronaldo played his first match for Corinthians on 4 March 2009, a Copa do Brasil match against Itumbiara at Estádio Juscelino Kubitschek, in which he came as a substitute for Jorge Henrique. Ronaldo scored his first goal for Corinthians on 8 March 2009 in a Campeonato Paulista match against Palmeiras. Scoring eight goals in nine matches, his form led to calls for his return to the Brazil national team – nearly 70% of respondents in a poll for the O Globo newspaper voted that he should be reinstated, with the country's president Lula also calling for his immediate return. He scored twice in a 3–1 win against local rivals Santos in the first leg of the state championship final, with Santos idol Pelé looking on from the stands. His second goal, a chip over the Santos goalkeeper from 30 yards out, sent the Corinthians fans into hysteria. Ultimately, he helped Corinthians win the Campeonato Paulista with 10 goals in 14 games.
Ronaldo scored in Corinthians 4–2 aggregate defeat of Internacional in the final of the 2009 Copa do Brasil, helping the club win the trophy for the third time (the second of his career), thus earning a spot in the Copa Libertadores 2010. Following an injury lay off he returned on 20 September in a match against Goiás, and a week later scored for Corinthians in a draw against São Paulo FC. He finished the Brazilian Serie A 2009 with 12 goals in 20 matches.
Ronaldo greets fans at the Emirates Stadium in London in March 2011, one month after announcing his retirement
In February 2010, Ronaldo signed a contract extension with Corinthians that would keep him with the club until the end of 2011, and said he would then retire. Commenting on his weight issues following this announcement, Brian Homewood of The Guardian states, "Sadly, Ronaldo's celebrity is now more of a draw than his skills on the pitch – Coldplay, Israeli prime minister Shimon Peres and actor Hugh Jackman have all visited São Paulo to get a picture with the roly‑poly star."
In February 2011, after Corinthians were eliminated from the 2011 Copa Libertadores by the Colombian team Deportes Tolima, Ronaldo announced his retirement from football, concluding an 18-year career. In an emotional press conference on 14 February, he cited pain and hypothyroidism as the reasons for his premature retirement. He discovered he had hypothyroidism – a condition which slows down metabolism and causes weight gain – during tests with Milan in 2007. Ronaldo admitted his body had finally succumbed to the crippling litany of injuries that had blighted his career: "It's very hard to leave something that made me so happy. Mentally I wanted to continue but I have to acknowledge that I lost to my body. The head wants to go on but the body can't take any more. I think of an action but I can't do it the way I want to. It's time to go."