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. 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 one seed of the qualification, Thomaz Bellucci. 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. 2010: Top 250 debut, First Challenger title 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. He bounced back a week later by qualifying at the Honolulu Challenger, but lost to Donald Young in the second round. Dimitrov then participated for Bulgaria in the Davis Cup, claiming all three wins in a 3–2 victory over Monaco. Following the Davis Cup tie, Dimitrov had a number of early losses in various challenger tournaments. Dimitrov won his first ATP tour match of the year on the grass courts of the Aegon Championships in London. He beat Alex Bogdanovic before losing to world No. 31, Feliciano López, in the second round. He then had a great run in the Marburg Open, a Challenger event, where he came through qualifying to reach the semifinals where he lost out to Simone Vagnozzi. Dimitrov again had a number of disappointing losses in Challenger events and another Davis Cup tie. Dimitrov then participated in four futures tournaments, posting impressive results, including two tournament victories in Germany, and another in Spain. Dimitrov gained enough points to enter the world's top 250 for the first time in his career. His recent good form translated to the Challenger Tour, capturing three consecutive titles, the first coming at the IPP Trophy, defeating Pablo Andújar in three sets. And back to back titles at the Bangkok Open, where he beat former top 20 player Dmitry Tursunov in the quarterfinals and Konstantin Kravchuk in the final, and at the Bangkok Open 2 defeating Alexander Kudryavtsev. He