Bolelli has not yet won a single title on the ATP World Tour . At the BMW Open in Munich in 2008 he reached his first and so far only ATP final, in which he had to admit defeat to the Chilean Fernando González .
From 2007 to 2009 Bolelli played for the Italian Davis Cup team . He played seven games during this period, of which he won three. At the Davis Cup 2007 against Israel he lost to Noam Okun , but won against Dudi Sela . At the Davis Cup in 2008 against Croatia he lost the singles against Ivo Karlović as well as the doubles with Potito Starace against Mario Ančić and Marin Čilić , but he won his singles against Ančić. In 2009, Bolelli resigned from the Davis Cup team in order to concentrate fully on his own career, which at that time had reached its peak (best ranking with 36th place on February 23, 2009).
On February 1, 2010, Bolelli fell out of the top 100 for the first time in three years. In 2010 he returned to the Davis Cup team and in September 2011 against Chile he contributed to the rise of Italy with a win in singles and doubles with Fabio Fognini in the world group. At the first round match of the world group in February 2012 against the Czech Republic , Bolelli celebrated the only victory of his team (6: 4, 6: 4 against František Čermák ). In 2011 he won the doubles competition at the BMW Open in Munich, when he and Horacio Zeballos beat Andreas Beck and Christopher Kas 7: 6, 6: 4. In the same year he succeeded at the ATP tournament in Umag with compatriot Fognini against Marin Čilić and Lovro Zovko with 6: 3, 5: 7, [10: 7] his second double success on the tour.
At the Australian Open , Bolelli reached the second round with Fognini in 2012, so he improved to 37th in doubles. In singles, he improved to 110th place by beating Blaž Kavčič at the Challenger tournament in Florianópolis . In February 2013, he celebrated together with Fognini in Buenos Aires in the final against Simon Stadler and Nicholas Monroe his third double title. He won his fourth again in 2015 at the side of Fognini at the Australian Open ; it was his first Grand Slam title. In doubles he was 27th, his new record.
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Italy
Ivo Minář
Tunis (1)
Andrei Pavel
Bratislava
Alejandro Falla
Eduardo Schwank
Florianópolis
Blaž Kavčič
Fabrice Martin
Jan-Lennard Struff
Mate Delic
Fernando González
Australian Open
Dubai
Feliciano López Marc López.svg){kind=small}
Moscow (1)
Acapulco
Łukasz Kubot David Marrero
Vasek Pospisil Jack Sock
Monte Carlo
Shanghai
Raven Klaasen Marcelo Melo
Båstad
