The 10 greatest long shots to win the Preakness Stakes, including Master Derby and Shackelford

By Scott Gulbransen

·Updated: May 14, 2024

Oxbow Preakness Stakes long shot — Credit: Mitch Stringer-USA TODAY Sports

The Preakness Stakes has a rich history of dramatic finishes and unexpected triumphs. Among these stories are the long shots who beat the odds to claim victory at the historic Pimlico Racecourse outside Baltimore, Maryland. This year, 150th Kentucky Derby winner Mystik Dan will be in the field hoping to keep his Triple Crown hopes alive in what is shaping up to be an exciting and competitive race. Here’s our list of the Top 10 long shots to ever win the legendary Preakness Stakes.

10. Shackleford (2011)

Coming in at 12-1 odds, Shackleford’s victory in the 2011 Preakness Stakes was a testament to his strength, determination and front-running style. He managed to hold off a late charge from Kentucky Derby winner Animal Kingdom, showcasing his tenacity and ability to maintain speed under pressure. He won by just a half-length, but as a double-digit underdog, he excelled when it mattered most.

9. Cloud Computing (2017)

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Cloud Computing, a 13-1 long shot, capitalized on a perfect run to edge out Classic Empire in the 2017 Preakness Stakes. His victory highlighted the strategy of his trainer, who chose to skip the Kentucky Derby to focus on the Preakness, resulting in a well-rested and ready champion. Ridden by jockey Javier Castellano, Cloud Computing ran 1 3/16 miles in 1:55.98.

8. Oxbow (2013)

At 15-1 odds, Oxbow’s wire-to-wire victory in the 2013 Preakness Stakes was a masterclass in pace-setting. Trained by D. Wayne Lukas and ridden by Gary Stevens, Oxbow defeated a competitive field that included Kentucky Derby winner Orb, proving his mettle on the Pimlico track. “Oxbow is a special horse,” Stevens said. “He has the speed of a sprinter, stamina of a classic winner and the heart of a champion.”

7. Aloma’s Ruler (1982)

Aloma’s Ruler, a 13-1 long shot, led the field from start to finish in the 1982 Preakness Stakes. His victory was a remarkable display of speed and stamina, as he managed to fend off a strong challenge from the Kentucky Derby winner, Gato Del Sol. Jack Kaenel rode him and won the race by half a length over runner-up Linkage.

6. Tabasco Cat (1994)

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With odds of 8-1, Tabasco Cat overcame a field of strong contenders to win the 1994 Preakness Stakes. His victory was particularly poignant as it marked the return to glory for trainer D. Wayne Lukas following personal and professional challenges. Tabasco Cat went on to win the Belmont Stakes that same year.

5. Deputed Testimony (1983)

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Deputed Testamony, a 14-1 long shot, delivered a stunning performance in the 1983 Preakness Stakes. Despite facing a field of strong contenders, including the Kentucky Derby winner Sunny’s Halo, Deputed Testamony showcased his exceptional stamina and speed despite a wet and sloppy track. His surprising victory not only thrilled racing fans but also solidified his place in Preakness history as one of the race’s most memorable underdogs.

4. Bee Bee Bee (1972)

Bee Bee Bee took the horse racing world by surprise when he won the 1972 Preakness Stakes as a 19-1 underdog, resulting in one of the biggest upsets in sports history. Despite being seen as an unlikely winner, Bee Bee Bee faced tough competition, including the strong favorite Riva Ridge, who had previously won the Kentucky Derby. Against all expectations, he showcased his talent and unwavering determination by starting swiftly, taking an early lead, and steadily maintaining his speed. His victory highlighted the unpredictable nature of horse racing. It celebrated the triumph of an underdog stepping up to shine bright on a big stage, solidifying his place in Preakness history.

3. Display (1926)

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In 1926, Display pulled off a remarkable upset by winning the Preakness Stakes at an incredible 19-1 odds, resulting in a payout of $40.70 for those who bet on him. Despite facing tough competition, Display wasn’t seen as a top contender. However, right from the start of the race, he proved everyone wrong. Display’s race tactics were impressive as he kept a consistent pace and was well-positioned early. Throughout the race, Display displayed his endurance and competitive spirit, making a decisive move toward victory in the final stretch. His surprising win left spectators in awe and highlighted the thrilling unpredictability of horse racing. Display’s triumph is remembered as a classic tale of an underdog seizing glory, securing his place in Preakness Stakes history as one of its most memorable long-shot champions.

2. Coventary (1925)

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Just a year before Display’s massive upset, Coventry surprised everyone in the racing world by winning the 1925 Preakness Stakes with a staggering 21-1 odds, which led to a nice $45.60 payout for those who bet on him — the equivalent of $794 today. Despite not getting attention from many people, Coventry showed impressive speed and stamina during the race. Starting with determination, he steadily moved up through the field, surpassing his competitors at every corner. He pushed forward to secure the win, leaving the favored competition in his dust.

1. Master Derby (1975)

Topping our list is Master Derby, whose 23-1 upset in the 1975 Preakness Stakes remains one of the most surprising and memorable victories in the race’s history. Defeating Kentucky Derby winner Foolish Pleasure, Master Derby’s triumph epitomized the unpredictable and thrilling nature of horse racing. Jockey Darrel McHargue rode Master Derby to victory by one length over runner-up Foolish Pleasure.

These 10 long shots have etched their names into the hallowed halls of Preakness Stakes lore, proving that sometimes, the biggest surprises come from those least expected to succeed.