A graduate of North Texas State University, Shepard played with the Pittsburgh Steelers in 1956, rushing for 91 yards in 12 games. He next joined the Blue Bombers in 1957 for an all-star 6-year stay. He would play in the Grey Cup championship game 5 of those years, winning 4 times. His best season was 1959, when he rushed for 1076 yards, was an all-star and was Grey Cup Most Valuable Player (rushing for 247 yards). He rushed for 3768 yards with the Bombers and was an excellent punter, never averaging less than 43.1 yards per punt in a season.
He has since been inducted into the Winnipeg Football Club Hall of Fame, in 1992, and the North Texas State University Athletic Hall of Fame in 2005. Charlie Shepard died July 23, 2009, age 76.