Singh completed his early education in the Jesuit Saint Michael's School, following in his two elder brothers' footsteps. He went on to Saint Joseph's Institution, then the normal progression of students at Saint Michael's School. He was not focused on academics, and entered the arts stream rather than the sciences stream after his Secondary 2 examinations, to his parents' disappointment. He performed well in his O Level examinations, enabling him entry into the newly-established National Junior College, then a prestigious government school in Singapore. Singh spent two years there, and then served his national service as an officer in the Singapore Army, before attending the National University of Singapore, where he read law.