The history of horse racing has featured some amazing upsets, and that’s what attracts many to the sport in the first place. Over the years the Kentucky Derby has been one of the biggest races, and featured some of the biggest upsets. The most recent underdog to prevail at Churchill Downs was Mine That Bird who won in 2009 with odds of 51-1. But the biggest upset ever happened in the 1913 race.

When the horses prepared for the start of the Kentucky Derby on May 10, 1913, Donerail was the very definition of a long shot, with odds of 91 -1. The favorites for the race were Foundation, Ten Point and Yankee Notions. Donerail had failed to impress when he finished 30 lengths back in a preparation race, and bookmakers ceased to pay any attention to the three year old.

Donorail’s jockey, Roscoe Goose, thought that the bookies had it all wrong. He knew that his mount struggled in sloppy conditions and that his poor performance in the mud was unlikely to be repeated on the big day. The way that the race unfolded was boringly predictable, until the final turn. The three favorites seemed to have matters under control as the horses entered the final stretch. As the shocked crowd looked on, Donorail showed them what Goose already knew. Donorail took the lead from Ten Point and was pulling away as the horses crossed the wire. When the dust settled, Donorail had not only won the race, but had also won it in record time.