Oleg Osenkov began studying classical music at age twelve and by his mid teens he was already performing in Samara, Russia. From 1991 to 1996 Oleg studied at the Samara University and at the same time he started performing with Samara Jazz Big Band.  In 1996 Oleg moved to Moscow where he studied both jazz and classical music with Anatoly Sobolev, Professor of Gnessins Academy of Music. In the same year, he enrolled at Moscow University with a Major in History of Arts and Culture (1996 – 1998). He has performed with the most famous musicians, such as the jazz star saxophonist Igor Butman, Oleg Kireev, among others. Leading and participating in numerous musical ensembles and various projects, Oleg Osenkov has performed in Russia, Poland, Germany, Estonia, Finland, among others. He appeared in several TV and Radio Shows. In 2002 Oleg participated in the Berklee World Scholarship Tour in Helsinki, where he received a scholarship for his education at Berklee College of Music.

In December 2002 Oleg moved to Boston, MA. In the last six years, Oleg Osenkov performed with different groups, appearing in jazz clubs, and at such venues as The Museum of Fine Arts, Institute of Contemporary Arts Theater, Top of the Hub, Ryles in greater Boston area, and Kitano, 55 Bar, Porters, Sophia, Fat Cat, Triad, Garage, Swing 46 in New York City. Oleg has performed at Swing’ in Mother Rest, NEMO, Beantown, Cape Code, Java, Mary Lou Williams Jazz Festivals. He has played with numerous world-class artists including Terri Lyne Carrington, Donny McCaslin, Ingrid Jensen, Ari Hoeing, Yoron Israel, Abraham Burton, Gene Jackson, Alex Sipiagin, Valery Ponomorev, Tiger Okoshi, Phil Wilson, and others. Since 2004 Oleg Osenkov lives and performs in New York City.

Mr. Oleg Osenkov has joined the faculty of the Piano School of NYC in 2009.