Since Thoroughbreds were first brought to the American colonies more than 300 years ago, match racing -- featuring one man's horse against another man's horse -- has been an important part of the sport of racing. In the 1800s, match races took place with regularity.
By the 20th Century, however, important match races grew fewer and fewer. A series of important international match races were held in 1923. During the 1930s and 1940s, there was another spike in interest in match racing, with a dozen or so contests being held involving national champions. Alsab met Whirlaway; Armed met Assault; Busher met Duranza; Capot met Coaltown; etc.
Arguably, the most famous match races of the current century could probably be counted on one hand. These include:
October 12, 1920
Horse of the Century Man o' War met Sir Barton, first horse to win what would later become the Triple Crown, at Kenilworth Park in Windsor, Ontario, Canada. While the cast was strong, the importance of the race suffered because it was widely recognized that Sir Barton was not at his best. Man o' War won in a gallop by 7 lengths.
November 1, 1938
Triple Crown winner and reigning Horse of the Year War Admiral, the great son of Man o' War, met the rags-to-riches people's horse, Seabiscuit, who would go on to be the Horse of the Year and the world's leading money winning Thoroughbred. The location was Pimlico Race Course in Baltimore, MD.