Dimitrov won his first doubles challenger title at the ATP Challenger Trophy with Teymuraz Gabashvili beating Jan Minář and Lukáš Rosol.He then received a wildcard at the If Stockholm Open but lost in the first round to Jarkko Nieminen.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, 13 years his senior, in a discreet relationship.Despite this he attempted to continue but lost the following 10 games before he retired.He was granted a wildcard to the main draw of the Catella Swedish Open but lost in the first round to Guillermo Cañas.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.He reached the 2nd round of the Aegon Championships after defeating Iván Navarro, but lost in two tiebreaks to Gilles Simon.In Wimbledon where he got a wildcard as the 2008 Juniors Champion he won the first set of his first round match against Igor Kunitsyn but then suffered a knee injury.He then completed two victories in the Davis Cup against Hungary.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.Dimitrov is also the first (and only) Bulgarian male tennis player to win an ATP title in singles (after he won in October 2013 at Stockholm) and reach a final in doubles (in 2011) as well as the only Bulgarian male player to reach the third round or better at a Grand Slam tournament.Dimitrov is also the first Bulgarian to qualify for, and later win, the ATP Finals. Prior to his professional career, Dimitrov enjoyed a successful junior career, in which he held the world No.On his way to the title he also defeated top seed Tsung-hua Yang of Taiwan in the semifinals. In 2008, Dimitrov began frequent participation in men's events.After the tournament Dimitrov announced that he was ending his junior career and focusing on improving his ATP ranking. His first title came on clay at a futures tournament in Barcelona.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.