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With Vasek Pospisil, he reached the US Open doubles final falling to Jonathan Eysseric and Jérôme Inzerillo.
He began the 2008 Grand Slam season with a quarterfinal showing at Roland Garros, losing to Poland's Jerzy Janowicz in three sets.
The victory saw him join former junior champions Roger Federer and Stefan Edberg and guaranteed him a wildcard entry into the 2009 Wimbledon men's draw.
122 Jiří Vaněk in three sets in the first round for his first ATP level win, before losing to Julian Reister.Dimitrov began dating Maria Sharapova in late 2012.He and Sharapova only confirmed their relationship after the 2013 Madrid Open where the Bulgarian managed his first win against a world No. At the beginning of 2016, he started dating Nicole Scherzinger in a discreet relationship.In 2009, he was granted a wildcard to the main draw of the ABN AMRO World Tennis Tournament and scored an upset over then world No. He was granted a wildcard to the main draw of the Open 13, but lost to world No.23 Tomáš Berdych, earning his first ATP main draw win. 8 Gilles Simon in the first round, despite serving for the match at ninth game of the third set.