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As the 2008 winner of the US Open Boys Tournament he was granted a wildcard for the US Open Qualification Tournament.
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.
A year later, Dimitrov moved to Paris, France, where he joined Patrick Mouratoglou's Tennis Academy and spent the next four seasons there.
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 reached the quarterfinals of the challenger Open Castilla y León losing out in three sets to Marcel Granollers.
He then lost in the second round to Martin Fischer in straight sets at the American Express – TED Open.