Roy Franklin Fleming was born in 1878 or 1879 in Derby Township, Ontario. He studied to become an elementary school teacher and, at the age of 17, passed his Province of Ontario Education Department examinations. Between 1896 and 1900, Fleming taught at various schools in Ontario until enrolling in the Toronto Normal School for a year. He attended Kingston Art School for seven months in 1902-1903 and simultaneously served as a school principal in that city until 1904.

In 1905, Fleming left Ontario to study at the New York School of Art (later, Parsons The New School for Design), where his teachers and lecturers included William Merritt Chase, Robert Henri, and Frank Alvah Parsons. He joined the Art Students League and attended classes at the DeWitt Clinton Night Technical School, a pioneering educational institution that had opened in 1897. Fleming earned a certificate in Normal Art Training from the New York School of Art in June 1907. Shortly thereafter, he returned to Ontario to serve as drawing master of the Normal School of Ottawa, and taught there until his retirement in 1940. The Normal School of Ottawa eventually became the Faculty of Education at the University of Ottawa.

During his tenure at the Normal School, Fleming was involved in a range of other activities. He lectured at the University of Toronto and other schools throughout the province; edited art textbooks at the behest of the government of Ontario; and practiced carpentry, building houses for himself and his brother. An amateur historian, Fleming also wrote about Ontario's history and investigated a shipwreck for the Canadian Department of Public Works.

Roy F. Fleming died in 1958.