Roland was born in rural West Tennessee. He attended Freed-Haldeman University and then transferred to Vanderbilt University in Nashville, TN. From 1938–1940, he taught high school in his native county and then served as a historian for the National Park Service. In 1941 he joined the US Army and was a captain in the infantry in the European Theater. He fought in the 1944 Battle of the Bulge and earned a purple heart.
After his service, he completed a Ph.D in history from Louisiana State University. After his graduate studies, Roland returned to the military during the Korean War as the assistant to the chief historian of the Army. He then pursued his academic career, teaching from 1952 to 1970 at Tulane University. He then taught another eighteen years from 1970 to 1988 at the University of Kentucky in Lexington, KY.