In May, Bolleli reached his maiden final at the clay-court 2008 BMW Open tournament in Munich, where he was defeated by Fernando González.

In September, Simone Bolelli was banned by The Italian Tennis Federation from national team events for skipping the Davis Cup tie with Latvia in Europe-Africa zone relegation playoff.

Bolelli said that he had told Italy captain Corrado Barazzutti well in advance of the tie that he preferred to work on his fast-court game in Asia.

[1][2] At the 2015 Australian Open, Bolelli and Fabio Fognini captured their first Grand Slam championship doubles title.

The Italian duo, playing their ninth major together, defeated French pair Pierre-Hugues Herbert and Nicolas Mahut in straight sets 6–4, 6–4 in the final.

In February 2016, Bolleli won his second biggest title in doubles at the ATP 500 2016 Dubai Tennis Championships with Andreas Seppi.

At the 2022 Australian Open he reached the quarterfinals with Fabio Fognini where they lost to second seeded pair Rajeev Ram and Joe Salisbury.

[10] Bolelli and Vavassori won the China Open in October, defeating third seeds Harri Heliövaara and Henry Patten in the final.

[11][12][13] Vavassori and Bolelli won the Adelaide International, defeating Kevin Krawietz and Tim Pütz in the final.

[14] The pair reached the final at the Australian Open, losing to sixth seeds Harri Heliövaara and Henry Patten.