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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.He won his first round match against Tobias Kamke but in the second round lost to the number 1 seed of the qualification Thomaz Bellucci.Dimitrov won his first doubles challenger title at the ATP Challenger Trophy with Teymuraz Gabashvili beating Jan Minář and Lukáš Rosol.He lost to Danai Udomchoke in straight sets in the second round of the SAT Bangkok Open. He then reached the quarter finals after qualifying of two successive challengers at the Trofeo Paolo Corazzi and Aegon Trophy.He reached the 2nd round of the Aegon Championships after defeating Iván Navarro, but lost in two tiebreaks to Gilles Simon.He was granted a wildcard to the main draw of the Catella Swedish Open but lost in the first round to Guillermo Cañas.He reached the quarterfinals of the challenger Open Castilla y León losing out in three sets to Marcel Granollers.

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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.However he went on to win Wimbledon after defeating Henri Kontinen of Finland in the final.Dimitrov then participated for Bulgaria in the Davis Cup, claiming all 3 wins in a 3–2 victory over Monaco.Following the Davis Cup tie, Grigor had a number of early losses in various challenger tournaments. He then had a great run in the Marburg Open, a challenger event, where he came through qualifying to reach the semi-finals where he lost out to Simone Vagnozzi.

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