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 match continued until 22:38, the latest ever finish in Wimbledon history (this record was broken in 2012 in a third round match between Andy Murray and Marcos Baghdatis, which ended at 23:02). These were the only two matches in which the Centre Court roof was used during the entire 2009 tournament. The Tennis Integrity Unit (TIU) planned to observe matches played by up to 12 players (some of whom were inside the ATP top 50) throughout the tournament. The TIU has existed since January 2008. The ATP claimed to have identified Russian and Italian Mafia-related groups behind suspicious betting at