He has worked with such musicians as Gato Barbieri, Chick Corea, Bill Frisell, Sol Gabetta, Richard Galliano, Trilok Gurtu, Chuco Valdes, Egberto Gismonti, Lee Konitz, Bobby McFerrin, Pat Metheny, Caetano Veloso, Phil Woods, Hector Zazou and has recorded more than 15 albums with trumpeter Enrico Rava.

In the same year, he played for the first time with American saxophonist Lee Konitz in TenderLee for Chet, and won the prize for best new talent awarded by Italian magazine Musica Jazz.

Bollani's collaborations in the first years were not limited to jazz, but included works with Italian pop artists such as Elio, Irene Grandi, Marco Parente, Peppe Servillo, Bobo Rondelli, Banda Osiris, Bandabardò, Massimo Ranieri.

Furthermore, Bollani featured in several albums and international tours where he played with such musicians as Gianni Basso, Gianluca Petrella, John Abercrombie, Jeff Ballard, Larry Grenadier, Paul Motian, Mark Turner, Phil Woods, Gato Barbieri and Pat Metheny.

[7] The last of the four albums was released in 2006, titled I visionari and recorded with the homonym band formed by Mirko Guerrini, Nico Gori, Ferruccio Spinetti and Cristiano Calcagnile, with special features by Mark Feldman, Paolo Fresu and Petra Magoni (at the time his wife)[8][deprecated source].

During these same years, Japanese label Venus Records released four albums by the “Stefano Bollani Trio” formed with Ares Tavolazzi on contrabass and Walter Paoli on drums: Black and Tan Fantasy (2002), Volare (2002), Falando de amor (2003), Ma l'amore no (2004) and I'm in the Mood for Love (2007).

The following year, Bollani tackled classical repertoire with the Filarmonica '900 of the Teatro Regio of Turin, directed by Jan Latham-Koenig, by recording the Concert champêtre, Les Animaux Modèles, and the Improvisations number 13 and 15 by Francis Poulenc.

On September 14, the award was presented on the main stage of the Umbria Jazz Festival in Perugia, Italy by Berklee's former vice president of academic affairs, Larry Monroe.

The numerous concerts with symphonic orchestras – directed by Daniel Harding, Kristian Järvi, Zubin Mehta, Gianandrea Noseda and Antonio Pappano among others – did not keep Bollani from recording various albums with other artists, such as Big Band!, with the Hamburg-based NDR Bigband directed by Norwegian saxophonist Geir Lysne (2011; Echo Jazz award 2013[15]), Irene Grandi & Stefano Bollani (2012), O que será with Hamilton de Holanda (2013), Sheik Yer Zappa, a tribute to Frank Zappa's music (2014).

Also in 2014, Bollani again recorded with the Danish Trio releasing Joy in Spite of Everything featuring Mark Turner and Bill Frisell,[16] which was conferred the Best Album of the year award by Musica Jazz.

The following year the new album Live from Mars was released and the project Napoli Trip begins: Bollani pays tribute to Neapolitan music accompanied by Daniele Sepe, Nico Gori, Manu Katché and Jan Bang, and alongside Arye Henriksen, Audun Klive and Hamilton de Holanda.

There is also a cartoon character based on Bollani, named Paperefano Bolletta, who appeared for the first time in the Italian version of the Disney magazine, Donald Duck pocket books (Topolino), on 22 September 2009.