C.S. Weerasooriya was enlisted into the Ceylon Army on 09 May 1963 as an Officer Cadet. He was a member of the first batch that was trained at the Pakistan Military Academy from 1963 to 1965.
He was commissioned on 11 September 1965 into the 4th Regiment Ceylon Artillery.
Over the years, C.S. Weerasooriya followed the Regimental Officers Survey Course, Long Gunnery Staff Course, and the Senior Command (Artillery) Course, all of these in India.
On 08 March 1985, he was promoted to the rank of Lieutenant Colonel, subsequently assuming the role of Commanding Officer of the 4th Field Artillery Regiment from March 1985 to March 1987. His dedication and competence led to his promotion to Colonel on 01 October 1988 and Brigadier on 01 May 1989.[5] In 1994, C.S. Weerasooriya followed the National Defense College Course in New Delhi, India, subsequent to which he was promoted to the rank of Major General.
During his military career, apart from regimental appointments, he held the appointment of Military Assistant (MA) to the Commander, Gen Denis Perera, in 1981. Thereafter, he held the senior appointments of Regimental Commander Artillery, CommandantArmy Training Centre Diyatalawa, Commander 22 Brigade and Coordinating Officer Trincomalee, Commander 12 Brigade Colombo, Commander 1 Brigade and Coordinating Officer Ampara District, Commander 5 Brigade Group Mannar and Coordinating Officer Mannar District, Commander Artillery Brigade, Director Operations Army Headquarters (D Ops), General Officer Commanding Task Force 1 and Coordinator in Chief Jaffna District, Overall Operations Commander - Joint Operations Headquarters - Vuvuniya, Deputy Chief of Staff, and Chief of Staff.[6]
In 2000 he was appointed as Sri Lankan High Commissioner to Pakistan and served in this capacity for six years. Pakistan signed its first ever Free Trade Agreement, during C.S. Weerasooriya's tenure as High Commissioner, with Sri Lanka. His close friendship with former Chief of Army Staff and President, Pervez Musharraf, resulted in much support being given by Pakistan towards Sri Lanka's war effort, during C.S. Weerasooriya's tenure as High Commissioner.
Upon his return to Sri Lanka, C.S. Weerasooriya served as an Independent Non-executive Director of Ceylinco Life PLC from 2010 to 2022[11].[citation needed] and as the International President of the Association of Military Christian Fellowships (AMCF), from 2012 to 2022.[12][13][14] He was the first South Asian to hold this position.