Biggest Preakness Stakes Upsets in Horse Racing History

Horse racing upsets are some of the most exciting moments to witness in sports. The horses on this list have the favorite they defeated and their odds before the race.

Coventry won the Preakness Stakes by 4 lengths from Backbone in 1925. Backbones was a huge favorite. Coventry was 21.8-1 longshot. He won five races and earned $52,825. The stallion was sold for $25,000 to a carpet manufacturer.

Display won the Preakness in 1926. John Maiben rode Display. Display won by a head over Blondin. The next year the prize money was increased to $63,625. Coventry won in the same year. Coventry won with a record of 23-25-19.

Bee Bee Bee won the 1972 Preakness Stakes. Riva Ridge was the favorite. The horse won by 1 ½ lengths. BeeBeeBee won $135,300 of the $200,000 prize money. The stallion earned $281,098 in his career.

Master Derby won the 1975 Preakness Stakes. Foolish Pleasure finished second. Master Derby took home $158,100 for first place. The horse won $698,625 in career. The following year Master Derby won Louisiana Derby Trial Stake, Calumet Purse and Blue Grass Stages.

Deputed Testamony beat Sunny’s Halo in the 1983 Preakness Stakes. Sunny's Halo was a huge favorite to win. Deputed's victory made up for his career earnings of $674,329. He was the oldest living horse to have won a triple crown race when he died at 32.

Charismatic won the Kentucky Derby at 31-1 odds. In 1999, a horse named Menifee was favored to win the triple crown race at 2-2 odds, but Charismatics won it. The horse was disrespected by the oddsmakers. Charisticatic went on to have $2,038,000 in career earnings.

Oxbow beat Orb at the Preakness Stakes in 2013. Orb had been the favorite before the race. Itsmyluckyday placed second and brought home $200,000. Mylute finished third and took home an impressive $110,00.

Rich Strike won the Kentucky Derby at 80-1 odds. A $30,000 bet on Rich Strike would have cashed into $2.4 million. The best way to spot an upset is to consider everything. If a horse has a good track record and is being disrespected odds-wise, that could make for a great bet.