French Open: QF (2008) Wimbledon: W (2008) US Open: W (2008) Professional career 2008: ATP debut In 2008, Dimitrov began frequent participation in men's events. His first title came on clay at a futures tournament in Barcelona. His first ATP level match was at the Ordina Open where he lost to Igor Andreev in straight sets. After his junior US Open title he won back to back futures tournaments in Madrid on hard court and rose 300 places to career high ranking of 477. The achievement attracted enough attention to earn him a wildcard into the Mutua Madrileña Madrid Open qualifying draw where he lost to then No. 64, Florent Serra of France. After being granted another wildcard to the Davidoff Swiss Indoors qualifying draw and defeated No. 122, Jiří Vaněk, in three sets in the first round for his first ATP level win, before losing to Julian Reister. 2009: First ATP match win, Grand Slam debut 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. 23, Tomáš Berdych, earning his first ATP main draw win. In the second round he faced world No. 1, Rafael Nadal, and lost in three sets. He was granted a wildcard to the main draw of the Open 13, but lost to world No. 8, Gilles Simon, in the first round, despite serving for the match at ninth game of the third set. 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. Four first round exits in Challengers followed. He then reached the quarterfinals after qualifying of two successive Challengers at the Trofeo Paolo Corazzi and Aegon Trophy. He reached the second round of the Aegon Championships after defeating Iván Navarro, but lost in two tiebreaks to Gilles Simon. On his Grand Slam debut at the 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. Despite this he attempted to continue but lost the following ten games before he retired. He was granted a wildcard to the main draw of the Swedish Open but lost in the first round to Guillermo Cañas. He reached the quarterfinals of the