His early gurus include his father Late Ajit Kumar Chakraborty, Pannalal Samanta, Kanaidas Baigari, and later on, Guru Jnan Prakash Ghosh and Ustad Munawar Ali Khan (son of Ustad Bade Ghulam Ali Khan). He has also learned from Ustad Latafat Hussain Khan, Pt. Nibruttibua Sarnaik, Vidushi Hirabai Barodekar, Dr. M. Balamuralikrishna, among others. Because of his extensive training, he is not only a doyen of the Patiala-Kasur style, but can also portray the key features of other major classical gharanas like Delhi, Jaipur, Gwalior, Agra, Kirana and even Carnatic music. Despite such a strictly classical training, Pandit Ajoy Chakrabarty is also renowned for his rendering of lighter genres like Thumri, Tappa, Geet, Bhajan, Keertan, Folk, and Film. He graduated first-class-first both in B.A and M.A from Rabindra Bharati University of Kolkata, and joined the ITC Sangeet Research Academy in 1977–78 as the first scholar. He then rose to the positions of Gold Medalist Fellow, member of the Expert Committee, and senior Guru.
Pandit Ajoy Chakrabarty is considered one of the vocal legends of Indian Classical music. He is notable for imagination and sensitivity to lyrics, coupled with his uncanny sense of rhythm. Recipient of as many as 4 prestigious awards of highest order from the President of India – Padma Shri (2011), Sangeet Natak Akademi (Delhi, 1999–2000), Kumar Gandharva (National Award, 1993) and the Best Male Playback Singer (Bengali Film "Chhandaneer"1990) – Pandit Ajoy Chakrabarty has received felicitation from both the former and present Chief Ministers of West Bengal. The first Indian vocalist invited by the Pakistan and Chinese governments, Pandit Ajoy Chakrabarty has performed in innumerable concerts and is still participating in all prestigious music conferences and festivals, including Dover Lane, Rabindra Sadan, Kala Mandir, Science City in Kolkata; Sanmukhananda, Nehru Centre, NCPA in Mumbai; Kamani and Sirifort in Delhi; Carnegie and Kenedy Centre in USA, Royal Albert and Queen Elizabeth in England; Theatre De La Ville in France to name a few. He also was awarded Honorary Citizenship in New Orleans, USA after performing with Jazz musicians at Preservation Hall, the birthplace of jazz music. Thus far, Pandit Ajoy Chakrabarty has recorded over 100 albums, mostly published from India, USA, Canada, UK, and Germany, composed of pure classical numbers including live performances and various other genres – Thumri, Dadra, Bhajan and other devotional songs like Shyamasangeet and many Bengali numbers, including songs of Tagore and Qazi Najrul Islam. Inspired by the ideals of his Guru Jnan Prakash Ghosh, Pandit Ajoy Chakrabarty founded Shrutinandan – A Music Kingdom, a musical institution designed to preserve and perpetuate the tradition of Indian Raga music. By the late 90s, he started to nurture young and budding talents in his music school, and it has since developed into a 1000+ strong body after a period of a decade and a half. Still today, every aspect of Shrutinandan, particularly the development of each student, is closely monitored by Pandit Ajoy Chrakrabarty himself, along with a group of 35 teachers, personally trained by him. The success of his teaching method is demonstrated by his daughter and disciple Kaushiki Chakrabarty, who is accepted globally as the torch-bearer of the Shrutinandan Concept and as an accomplished female vocalist. Along with her, Shrutinandan has produced a dozen other vocalists and instrumentalists of international acclaim in this period of time.
Ajoy Chakrabarty is married to Chandana Chakrabarty and their daughter, Kaushiki Chakrabarty is an accomplished female vocalist of Hindustani classical music. Their son, Ananjan Chrakrabarty is a sound engineer and upcoming music director/producer.