Which racehorse won 20 of 21 starts and lost only to Upset?

Man o’ War won 20 of 21 starts and lost only to Upset.

Man o’ War was one of the most dominant American racehorses of the early twentieth century. His sole defeat came in the 1919 Sanford Stakes at Saratoga, where Upset finished ahead of him in a famous upset that gave the winning horse its memorable name.

Man o’ War won major races including the Preakness Stakes and Belmont Stakes in 1920, although the Kentucky Derby was not part of his campaign. He was not entered in that race because his owner, Samuel Riddle, disliked the Derby’s distance and crowded field at the time.

The horse’s record is often stated as 20 wins from 21 starts. His only loss was by a narrow margin, and he later defeated Upset in a rematch. Man o’ War became an influential sire and remained a major figure in American racing history after retirement.