In May 2003, Vanderlei Luxemburgo, then coach of Cruzeiro, bought the services of Maldonado. At the time of the purchase, Maldonado's then girlfriend was Luxemburgo's daughter. Nevertheless, while with Cruzeiro, Maldonado experienced the most success of his career. In 2003, he played for the first team in the history of Brazilian football to win the triple crown.
For the 2006 season, Maldonado was reunited with former Cruzeiro's coach Luxemburgo at Santos However at the end of the Brazilian season was scheduled to have ankle surgery which caused him to miss up to two months. After recuperating Maldonado continued playing for Santos reaching the semi-finals of the 2007 Copa Libertadores. Currently Santos has completed the 2007 Campeonato Brasileiro Série A in second place and are eligible to compete in the upcoming Copa Libertadores 2008. He was being tracked by Fenerbahçe, Milan, Real Madrid and Ajax but no firm offers better than Fenerbahçe have been made. At 28 he was at the peak of his potential and European teams wanted to capitalise on this, but they were probably put off by the 8 red cards that he had received in the previous 3 years at club level.
Fenerbahçe
On the beginning of 2008 Maldonado signed with Fenerbahçe in 1½ year contract, at that time managed by Zico. The transaction was via C.A. Rentistas, which the proxy club paid Santos R$2,225,040. He struggled with injuries and spend a little more than a year in the Turkish club.
On August 27, 2009, Flamengo signed a 1-year contract with Maldonado. His debut for his new club was as a substitute in a 3-0 win against Santo André, but since his second match became a first team player. In his first ten matches Flamengo did not suffered any goal, nine of those playing alongside with Álvaro which signed with Flamengo at the same time, proving his was back at his high level. He scored his first goal for Flamengo after just few matches on November 8 against Atlético Mineiro. His good moment made Chile national team coach Marcelo Bielsa call him up to national team after a period absent. But his return to national team, on November 17 against Slovakia, wasn't as expected, Maldonado played well as a starter, although in the second half he suffered a serious injury in his left knee ligaments leaving out of the fields for four months. Maldonado signed a new 6-month contract in August 2010 and a 2-year contract in January 2011.
Career statistics
according to combined sources on the Santos official website Flamengo official website and Flaestatística.
International
Maldonado was selected to represent his country, Chile, at the 2000 Summer Olympics as a part of the Under-23 team that went on to win the bronze medal. Maldonado made his international debut on February 12, 2000, in a match versus Bulgaria. Since then Maldonado has appeared in 41 games with the adult squad and has netted one goal. For 2006 FIFA World Cup qualification, Maldonado was a regular with the first team and has since gained the captaincy of the national team. As of recent Maldonado has been called up to serve on the Chilean national team that is managed by Marcelo Bielsa.
