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 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.
