In 1999, he won the boys' singles event at Wimbledon. For many years, he was known as one of the best players on the tour not to have progressed past the third round of a Grand Slam event. He ended this streak by reaching the semifinals of the French Open in 2010, losing to Rafael Nadal after coming from two sets down to defeat Novak Djokovic in the quarterfinals. As of January 2020, he remains the only person to defeat Djokovic from two sets to love down. He has also had success in doubles, winning the men's doubles event at Wimbledon in 2010 and the US Open in 2011 with Philipp Petzschner, as well as the mixed doubles event at Wimbledon in 2011 with his then future (and later ex-) wife Iveta Benešová.