Kevin Freeman’s first international success came in 1963 when he won team gold and individual silver medals at the Pan American Games in Sao Paulo, Brazil.

Freeman represented the U.S. in three Olympic competitions. He was a member of the silver medal team at the 1964 Olympic Games in Tokyo riding Gallopade and placed 12th individually. At the following Games in 1968 in Mexico City, Freeman rode Chalan as a member of the silver medal U.S. team. At the 1972 Munich Olympics, Freeman was the highest placing American and won his third team silver medal aboard Good Mixture.

In 1991, Freeman was inducted into the Oregon Sports Hall of Fame. He was the organizer of the Freeman Farms Horse Trials in Oregon for many years and contributed much to the growth of the sport in Area VII.