Following the family tradition, Jayewardene entered the University College, Colombo in 1926 pursuing the Advocate's course, reading English, Latin, Logic and Economics for two years, after which he entered Ceylon Law College in 1928. He formed the College Union based on that of the Oxford Union with assistance of S. W. R. D. Bandaranaike who had recently return to Ceylon. At the Ceylon Law College he won the Hector Jayewardene Gold Medal and the Walter Pereira Prize in 1929. During this time he worked as his father's Private Secretary, while latter served as a Puisne Justice of Supreme Court of Ceylon and in July 1929, he joined three others in forming a dining club they called The Honorable Society of Pushcannons, which was later renamed as the Priya Sangamaya. In 1931, he passed his advocates exams, starting his legal practice in the unofficial bar.
