Sydney Hollinger Watson was born in Toronto, Ontario. He studied at the Central Technical School from 1926-28 in Toronto, Ontario.
He was employed as a commercial artist during the 1930's. From 1940-44, he was the Art Master at Lakefield Preparatory School. In 1946 he joined the Ontario College of Art first as a teacher, followed by the position of Vice-Principal of the Design Department from 1949-54, and finally Principal of the College from 1955-70.
Watson completed a number opf murals that are part of many major corporate headquarters, universities, churches and hospitals.
Watson was active in Toronto art circles and became an elected member of several art societies such as, the Canadian Society of Painters in Water Colour in 1942, the Ontario Society of Artists in 1947, where he served as President from 1952-54. In 1954 he joined the Canadian Group of Painters, that same year he was elected to the Royal Canadian Academy, as well as the National Industrial Design Council in 1955.
He has exhibited across Canada. His work is part of the public collections including at the Agnes Etherington Art Centre, Queen's University at Kingston, the McMichael Canadian Art Collection, the Robert McLaughlin Gallery, the Canadian War Museum, the National Gallery of Canada and Hart House, at The University of Toronto, among others.