Andy Murray match, a situation which Andy described as "awkward" and Jamie as "a bit weird". In the second Master Series tournament of the US Hard Court season, the Cincinnati Masters, Murray defeated veteran Mardy Fish in the second round, and then beat both Grigor Dimitrov and Richard Gasquet in three-set matches, having to come from a set down on both occasions, while Dimitrov had served for the match in the deciding set. In the semi-final, he lost to defending champion Roger Federer in straight sets, and after Federer went on to win the tournament, this result saw Murray return to the
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