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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. Prior to his professional career, Dimitrov enjoyed a successful junior career, in which he held the world No.

1 ranking and won the Boys' Singles titles at the 2008 Wimbledon Championships and the 2008 US Open.

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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.

Dimitrov started the season with a quarterfinal finish at a challenger event of Internationaux de Nouvelle-Calédonie.

He then attempted to qualify for the Australian Open, but lost in the first round to Robert Kendrick in three sets.

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.

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 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.

He bounced back a week later by qualifying at the Honolulu Challenger, but lost to Donald Young in the second round.