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 Ranked No. 312, Murray became the first Scot in the Open Era to reach the third round of the men's singles tournament at Wimbledon. In the third round, Murray lost to 2002 Wimbledon finalist David Nalbandian due to cramping and fatigue, having led two sets to love. Following Wimbledon, Murray won Challenger events on the hard courts of Aptos and Binghamton, New York. He then experienced his first Masters event at Cincinnati, where he beat Taylor Dent, before losing in three sets to then-No. 4, Marat Safin. With a wild card entry, Murray played Andrei Pavel in the opening round