Miles was one of the most versatile players in the history of the CFL during his eleven-year (1951–1961) career with the Edmonton Eskimos. As a defensive player (linebacker and defensive back), Miles intercepted 38 passes for 547 yards. As a special teams player, Miles returned punts (finishing with 279 punt returns for 2,085 yards) and kickoffs (88 returns for 2,131 yards), and punted on occasion. On offence, Miles was often found in a backfield with such CFL greats as Jackie Parker, Normie Kwong, Johnny Bright, Bernie Faloney and Don Getty; he could run or pass on the option with skill.
Selected as a CFL Western Conference All-Star eight times (three at running back, three at defensive back, two at linebacker) Miles was also named the Eskimos' team Most Valuable Player three times.
Miles played in five CFL Grey Cup championship games, winning three during the Eskimos' dynasty of successive Grey Cup titles in 1954, 1955, and 1956.[3] Miles played in the famous 1954 Grey Cup game with separated ribs, but still helped his underdog team win that classic game.
Miles received his Bachelor of Arts degree from the University of Alberta in 1956, and began work in the off season with the Edmonton Catholic School Board, where he taught school and organized high school sports. Miles continued working with the Edmonton Catholic School Board upon his retirement from the CFL in 1961.
Miles and his wife, Dr. Marianne Miles, had seven children: Craig "Tony" Miles, Rolanda Miles, Michelle Miles, Monica Lipscombe, Rollie Miles, Jr. (lineman on the University of AlbertaGolden Bears 1980 Vanier Cup national championship football team, and Most Valuable Player of the 1980 Churchill Bowl), Brett Miles (noted singer, songwriter and saxophonist),[5] and Mario Miles (co-founder of the Millwood Grizzlies Minor Football Association in Edmonton in 1996, and coach from 1996 to present).