Fleming played sixteen seasons in the Canadian Football League, all with the Eskimos. He is a four-time CFL West Division All-Star, (twice named CFL All-Star) and three-time Eskimos nominee for Most Outstanding Canadian. He has played in five Grey Cups, winning three, and named the 81st Grey Cup's Most Valuable Canadian. He kicked the game winning field goal in overtime for the Eskimos in the 93rd Grey Cup. Fleming holds the Eskimos' records for points (2,571), field goals (553), converts (713), punts (1,264), punt yardage (52,957) and kickoff yardage (69,973).