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
Andy Murray 4 sets. Murray leads 6–3 in ATP 1000 tournaments and 2–0 in finals. They have met five times at the ATP World Tour Finals, with Murray winning in Shanghai in 2008 and Federer coming out victorious in London in 2009, 2010, 2012, and in 2014. In August 2012, Murray met Federer in the final of the London 2012 Olympics at Wimbledon Centre Court, just four weeks after the 2012 Wimbledon Final, in which Federer had defeated Murray to win his record-tying 7th title at the All-England Club. Murray defeated Federer in straight sets to win the gold medal, denying Federer