After getting trained for a few years, Jaideep started playing in the junior level Tennis tournaments in India. He clinched the Junior National Championship in 1959. He also started showing his excellence in the international arena during the same period and in 1960, he ended as the runners-up in the Junior Wimbledon Singles Championships. Jaideep reached the peak of his career in the 1960s and 1970s. During this period he recorded wins in Helsinki, Stockholm and England. While winning these tournaments, he defeated some of the great Tennis players like Roy Emerson, Fred Stolle, John Newcombe and Arther Ashe.
Apart from getting individual success in various international Tennis events, Jaideep also played wonderfully for the Indian Davis Cup team. He made his debut in Davis Cup against Indonesia at Bangkok in 1960. He represented India in the Davis Cup for quite a long period of 13 years and during this period; he played 97 rubbers in 43 ties. Jaideep Mukherjee, Premjit Lall and Ramanathan Krishnan formed a deadly combination during that period and they were renamed the 'three musketeers', for their excellence. They took India to the inter-zone finals for four times, from 1960-63 and also in 1968. They also played brilliantly to help India reaching the Davis Cup Challenge round finals for the first time, against the Australians.
The biggest achievement in Jaideep Mukherjee's career came in the year 1966, during a Davis Cup tie against Germany at Kolkata. The Indian team was not in a good position in the tie and Jaideep almost single handedly clinched the tie for India by beating Ingo Budding in the first singles and later German No. 1, William Bungert in the reverse singles. The Government of India bestowed upon him the Arjuna Award in the year 1966, for his excellent achievements in Tennis. He retired from professional Tennis in 1972 and turned his attention towards Tennis administration and coaching. He joined the All India Tennis Association (AITA) and also one of the founder members of the Hero Sports Foundation.
Apart from playing for India and joining Tennis administration, Jaideep Mukherjee has also served as the non-playing captain of the Indian Davis Cup team from 1994-1999. Under his able leadership, the Indian team has successfully defeated the teams like Holland, South Korea etc. Apart from India, he has also coached the Malaysian Davis Cup Team. He is presently running one of the best Tennis training academies in India, named the Jaideep Mukherjee Tennis Academy at Kolkata. He has been instrumental in bringing the legendary Indian Tennis player, Leander Paes into limelight, who later went on to win Bronze medal at the Atlanta Olympic Games, in 1996. For his immense contribution to world tennis, Jaideep Mukherjee became the first Indian to be awarded the International Tennis Federation, lifetime Achievement Award in 2003.