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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 won the title without dropping a set despite playing with a shoulder injury throughout the tournament.

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.

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.

122 Jiří Vaněk in three sets in the first round for his first ATP level win, before losing to Julian Reister.

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.

He then received a wildcard at the If Stockholm Open but lost in the first round to Jarkko Nieminen.

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

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.

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