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After Wimbledon, Roddick began working with a new coach, tennis legend Jimmy Connors.
In his first event with his new coach, Roddick reached the final of Indianapolis, before losing to good friend and fellow American, James Blake.
In first-round Davis Cup action, Roddick helped the US defeat the Czech Republic, winning his singles matches against Ivo Minář and Tomáš Berdych.
Roddick reached at least the semifinals of his next two tournaments.
He then played a thriller five-set match against Fernando Verdasco, winning 6–2 in the final set.
Next, he beat Benjamin Becker, who was coming off a huge win against recently retired Andre Agassi.
Now in the semifinals for the first time since he won in 2003, Roddick played Mikhail Youzhny and beat him, 6–7, 6–0, 7–6, 6–3. He then qualified for the year-ending Tennis Masters Cup, where he defeated No.
1 shortly after he won the title at the 2003 US Open, defeating French Open champion Juan Carlos Ferrero in the final and overtaking him as the top-ranked player in the process.
Roddick was ranked in the year end top-10 for nine consecutive years (2002–2010) and won five Masters Series titles in that period.
Roddick and the Moroccan battled for five hours, with the fifth set (21–19 in favor of Roddick) at the time the longest fifth set in a Grand Slam tournament during the open era, at 2 hours and 23 minutes. In June, Roddick advanced to his first Wimbledon final, and after taking the first set from defending champion Federer, lost in four sets. At the 2004 Summer Olympics, Roddick lost to Chilean Fernando González, the eventual bronze medal winner, in the third round. There, he reached the fourth round, before being upset by unseeded and eventual finalist, Marcos Baghdatis.
Despite a lackluster French Open, Roddick enjoyed success in the United Kingdom by winning Queen's Club, beating No. It is one of three times that Roddick defeated Federer in an official ATP tournament. Roddick was knocked out during the 2004 US Open in a five-set quarterfinal against another big server, Joachim Johansson. At the French Open, Roddick retired in the first round, after sustaining a foot injury during the match.
Following a fourth-round defeat by Juan Martín del Potro, the 2009 US Open champion, Roddick retired from the sport with the aim of focusing on his work at the Andy Roddick Foundation.