D. R. Wijewardena was born as the third male child of seven sons and two daughters of Muhandiram Tudugalage Don Philip Wijewardene, a timber merchant of Sedavatta, Colombo and Helena Weerasinghe. He lost his father at a very young age and was raised by his mother. His brothers were Don Philip Alexander, Don Lewis, Don Charles, Don Edmund, Don Albert and Don Walter and his sisters were Harriot who married Dr Arthur Seneviratne and Agnes Helen who married Justice Eugene Wilfred Jayewardene. Wijewardena received his primary education at the Sedavatta School after which like all his brothers, completed his secondary education at St.Thomas College Mutwal. He then went on to study at Peterhouse, Cambridge. There he developed his interest in politics and met famous personalities such as future leaders of India like Lala Lajpat Rai, Bepin Chandra Pal, Surendranath Banerji and Gopal Krishna Gokhale. After graduating he became a Barrister at the Inner Temple.
Legal practice
Returning to Ceylon in 1912, he took oaths as an Advocate of the Supreme Court of Ceylon and started his legal practice at Hulftsdorp. He did not practice law for long, turning towards business activities instead.
In 1914, he acquired the Sinhala language daily Dinamina in 1914 together with his brother D. C. Wijewardena. He thereafter took over the English language daily The Ceylonese renaming it the Ceylon Daily News in 1918 and bought its primary competition Ceylon Independent. This was followed by the publication of a Tamil language daily Thinakaran. In 1926, these newspapers where consolidated under Associated Newspapers of Ceylon Limited which would publish seven newspapers Dinamina, Silumina Daily News, the Observer, Sunday Observer, Thinakaran and Sunday Thinakaran. ANCL was a subsidiary of the Lake House Group owned by Wijewardena which brought together his different publications which included the Fergusons Ceylon Directory.
Nationalist movement
In 1913, Wijewardena was elected Secretary of the Ceylon National Association, marking his formal entry into politics and together with its President Sir James Peiris he agitated for constitutional reform and self-rule. D. R. Wijewardena and E. W. Perera traced the location of the banner of last King Sri Vikrama Rajasinghe, the last king of the Kingdom of Kandy to the Royal Hospital Chelsea where it was kept since the surrender of the Kingdom to the British in 1815. The recovered banner became a focal point in the independence movement and it became the flag of the Dominion of Ceylon upon its independence in 1948. Wijewardena was in touch with local events and organised the first deputation to the Secretary of State for the Colonies with H. J. C. Pereira along with E. W. Perera. As a result of lobbying benefits Ceylonese were given another concession of a seat in the British dominated Legislative Council of Ceylon. To this seat majority of the Ceylonese elected Sir Ponnambalam Ramanathan against Sir Marcus Fernando. He would later organise a second deputation too. He was also instrumental in starting the Temperance movement and the Amadyapa Sabha.
