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Kitanovski started his musical education with Dragan Gjakonovski – Spato in 1979. From 1986–1990 he was the leader of the trio Spato, performing concerts and appearing on radio and television with the trio and as a soloist. He composed and arranged for the MBUC (Music and Ballet School) Chamber Orchestra and the MRT (Macedonian Radio Television) Dance Orchestra. He has recorded as a soloist for WDR in Cologne, Germany.
In the 1990s, he graduated from the Berklee College of Music. He composed for the jazz orchestra of Herb Pomeroy, the Greg Hopkins big band, and led groups of his own. He collaborated with performance artists Bart Uchida and Nancy Adams from Boston and wrote the solo act of Uchida in Taipei, Taiwan. Kitanovski returned to Skopje in 1997 and formed the band Luna. He appeared at the AFES Festival with the FMA Chamber Orchestra as composer and soloist. In 1998, in conjunction with the Skopje Jazz Festival label, he released his debut album, One for Charlie. Three years later he released the live album Duet with the same label.
- 1988 Robert Share Memorial Award
- 1992–95 Berklee Achievement Scholarship Award, given on three occasions
- 1994 Charles Mingus Award
- Live at Skopje Jazz Festival with Zoran Madjirov (SJF)
- One for Charlie (SJF, 1998)
- Borderlands with Cherkezi Orchestra (Enja, 2006)
- Georgievski, Nenad (24 December 2006). "Toni Kitanovski and Cherkezi Orchestra: Toni Kitanovski and Cherkezi Orchestra: Borderlands". All About Jazz. Retrieved 9 November 2017.