Rakesh Gupta began his legal practice in 1981. In 1995, he was appointed Secretary of the District Bar Association, and in 2001, he was elected as a Member of the Bar Council of Punjab and Haryana. Over the years, he served as President of the District Bar Association, Patiala, for seven terms. In 2006, he was elected Vice-Chairman of the Bar Council of Punjab and Haryana, during which he played a key role in establishing the Rajiv Gandhi National Law University in Patiala. In 2013, he was elected Chairman of the Bar Council of Punjab and Haryana.
During his tenure, the 5-year integrated law course was launched at Mohindra College, Patiala, and he laid the foundation stone for Law Bhawan in Amritsar. From 2001 to 2007, he also served as President of the Bar Association Patiala.