Andy Murray tie. At the Masters, Murray lost in the first round in Miami, Monte Carlo and Rome. Murray went out of the tournaments in Indian Wells and Hamburg in the second round. Murray reached his first Masters semi-final in Toronto at the Rogers Cup, losing to Richard Gasquet. At Cincinnati, Murray became only one of two players, alongside Rafael Nadal, to defeat Roger Federer in 2006, breaking the Swiss star's 55 match winning streak on hard courts. He lost two rounds later to Andy Roddick, but broke into the top 20 for the first time. In the final two Masters events
2009 Wimbledon Championships – Men's Singles 2009 Wimbledon Championships – Men's Singles Rafael Nadal was the defending champion, but withdrew from the tournament due to knee tendinitis. In a repeat of the 2004 and 2005 finals, Roger Federer defeated Andy Roddick in the final, 5–7, 7–6, 7–6, 3–6, 16–14 to win the Gentlemen's Singles tennis title at the 2009 Wimbledon Championships for the sixth time. It became the longest men's singles final (in terms of games played) in Grand Slam tournament history with 77 games, breaking the record of 71 games set at the 1927 Australian Open. The match also had the longest fifth set (16–14)