Cristiano Ronaldo at age 18 in 2003. After winning his first trophy, the FA Cup, during his first season in England, he helped United win three successive Premier League titles, a UEFA Champions League title, and a FIFA Club World Cup. By age 22, he had received Ballon d'Or and FIFA World Player of the Year nominations and at age 23, he won his first Ballon d'Or and FIFA World Player of the Year awards. In 2009, Ronaldo was the subject of the most expensive association football transfer when he moved from Manchester United to Real Madrid in a transfer worth €94
2008–09 Manchester United F.C. season miss from Tim Cahill, Everton ran out 4–2 winners on penalties and United's quest for five trophies was at an end. The draw for the Third Round of the 2008–09 League Cup paired Manchester United with Middlesbrough. The match was played at Old Trafford on 23 September 2008, and resulted in a 3–1 win for the home side, who gave debuts to three young players;Ben Amos, Danny Welbeck and Manucho. In his first start for the club since returning from injury, Cristiano Ronaldo opened the scoring in the 25th minute, heading home Ryan Giggs' corner. Adam Johnson equalised for Middlesbrough