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 Roddick fourth round, before being upset by unseeded and eventual finalist, Marcos Baghdatis. At the French Open, Roddick retired in the first round, after sustaining a foot injury during the match. Two weeks later at Wimbledon, Roddick was upset in the third round by British hopeful Andy Murray. This loss caused Roddick to fall below the top 10 for the first time since 2002. After Wimbledon, Roddick began working with a new coach, tennis legend Jimmy Connors. In his first event with his new coach, Roddick reached the final of Indianapolis, before losing to good friend and fellow American, James Blake.