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 have played 19 times with Murray leading 11–8. Murray leads 7–4 on hard courts and 3–0 on grass courts while Wawrinka leads 4–1 on clay courts. They have also met six times in Grand Slam tournaments with each player winning three matches. They have contested some close matches and one of their most notable matches was in the 2009 Wimbledon fourth round which Murray won in five sets and was the first men's match to be played under the Wimbledon roof, having the latest finish for a Wimbledon match at the time. Wawrinka also ended Murray's title defense at the