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
João Sousa of the season, where he lost to Thomaz Bellucci. At the French Open, Sousa beat Canadian Vasek Pospisil in straight sets in the first round, and was defeated by 3rd seed Andy Murray in the second round. In the men's doubles of the tournament, Sousa partnered with Bellucci and was knocked out in the first round by 11th seeds Jamie Murray and John Peers. In June, Sousa did not have a strong grass court season; he was defeated in the early rounds at the Rosmalen Grass Court Championships, the Queen's Club Championships and the Nottingham Open. At Wimbledon, Sousa was