Man o' War all-time greats with an "almost unbelievably brilliant performance" before a crowd of 25,000. At odds of 1-20, he faced only one rival, the well-regarded colt Donnaconna. Man o' War led from the start and Kummer let him run freely at the top of the stretch, allowing Man o' War to draw away by 20 lengths. Although eased in the final furlong, Man o' War set a world record of 2:14, beating the previous standard set in England by over two seconds and beating Sir Barton's American record by over three seconds. This time stood as the American record until 1961
Man o' War War in a bad position, getting boxed in by other horses then checked by tiring horses. Despite this, Man o' War came close to winning, losing by about a neck while conceding 15 pounds to Upset. It is sometimes erroneously thought that Upset's unexpected win popularized a new phrase in sports (meaning an underdog beating the favorite) – in fact, the term "upset" was already in use to describe such a situation for decades. The two horses faced off five times during their racing careers, with Man o' War beating Upset four times. The loss only enhanced Man o' War's