Robert Farah Maksoud in the third round in two close tie-break sets. Despite losing in the first round, Dimitrov became the first male Bulgarian player to rank inside the top 40 after the event. He then competed for Bulgaria in the Davis Cup against Finland, and won both his singles matches against Juho Paukku and Micke Kontinen, but lost his doubles in five sets (with partner Dimitar Kuzmanov) against Henri Kontinen of Finland and Harri Heliövaara. Finland ended up winning the tie 3–2. At the PBZ Zagreb Indoors, Dimitrov lost in the first round to Ivo Karlović in two tie-breaks. At the ABN AMRO World Tennis Tournament, Dimitrov beat Bernard Tomic and Nikolai Davydenko, and Marcos Baghdatis in three sets. In the semifinals, Dimitrov lost against world No. 7 and eventual champion Juan Martín del Potro in straight sets. At the BNP Paribas Open, Dimitrov became the first Bulgarian male tennis player to be seeded in a Masters 1000 event. In singles, he beat Matthew Ebden in two sets, but lost to world No. 1 Novak Djokovic in the third round. In doubles he partnered with Frederik Nielsen; they lost to Ivan Dodig and Marcelo Melo in the second round. At the Sony Open Tennis, Dimitrov beat Simone Bolelli, but lost to second seed Andy Murray in straight sets in the following round. In doubles with partner Frederik Nielsen, they reached semi-finals losing in straight sets against the eighth seeds, Mariusz Fyrstenberg and Marcin Matkowski. Dimitrov's next tournament was the clay-court Monte-Carlo Masters, where he reached the quarterfinals beating Xavier Malisse, eighth seed Janko Tipsarević, and Florian Mayer, all in straight sets, but lost in three sets to eight-time defending champion and third seed Rafael Nadal. This good run in Monte Carlo meant Dimitrov entered the top 30 in the ATP rankings for the first time, at No. 28. His next event was Barcelona Open Banco Sabadell, seeded 14th, he received a bye, but lost in the second round, despite leading 5–2 in the first set, he lost in straight sets to in-form Tommy Robredo. At the Madrid Open, following a victory over fellow 21-year-old Javier Martí, Dimitrov recorded the biggest win of his career, defeating world No. 1, Novak Djokovic in a three set match, in just over three hours. The two had met twice before, with Djokovic taking both encounters. In the third round, despite winning the first