Most Iconic Kentucky Derby® Wins

For more than a century, the Run for the Roses™ has brought together the sport’s finest horses, creating a stage where champions are made, records are set, and just about anything can happen. 

Some winners have etched their names into history with remarkable speed and commanding victories, while others have defied the odds to deliver the kind of thrilling upsets that become part of Derby lore for years to come.

Take a look back at some of the most iconic Kentucky Derby winners and the unforgettable moments that made their victories legendary. 

Secretariat (1973) 

Often regarded as the best racehorse of all time, Secretariat’s 1973 win remains one of the greatest performances in Kentucky Derby history. Lovingly known as “Big Red”, he started the race at dead last, but he did not stay there long. 

Secretariat began overtaking his opponents on the First-Turn before rounding the Final-Turn in fifth. Then, with incredible speed, he charged down the Homestretch, passing Sham to take the lead and cross the Finish-Line with a 2 1/2-length lead. The clock stopped at 1:59 2/5—a record-breaking time that has yet to be beaten. 

Big Red went on to sweep the Preakness Stakes and Belmont Stakes in record time, securing the Triple Crown™ with a breathtaking 31-length victory at Belmont Park and cementing his place among the greatest legends in thoroughbred racing. More than 50 years later, his records in all three Triple Crown™ races still stand. 

Seattle Slew (1977) 

All eyes were on Seattle Slew in 1977 as the superstar entered the Kentucky Derby as an undefeated contender looking to maintain the title. After a rough break from the starting gate, he lost several lengths, but he quickly recovered, moving along the inside until he was battling for first place alongside For the Moment. At the top of the Homestretch, Slew managed to pull away and secure the win by just 1 3/4 lengths. 

The colt maintained his undefeated record after the Derby, dominating the Preakness Stakes before leading the Belmont Stakes from start to finish. His victories made him the 10th Triple Crown™ winner and the first to complete the series while undefeated. Only one horse has matched the feat since—Justify in 2018. He also made history as the first horse in 136 years to capture the Triple Crown™ without racing as a two-year-old. 

Winning Colors (1988) 

At the start of 1988, few people had Winning Colors on their radar as a Kentucky Derby contender, much less a potential winner. But as the talented filly—yes, a female!—began racking up victories, it became clear she was anything but ordinary. After dominating the Santa Anita Derby with a 7 1/2-length victory over eight male competitors, Winning Colors defied expectations and earned her place in the Kentucky Derby. 

Facing some of the most talented male Thoroughbreds in the sport and testing her speed for an additional eighth of a mile, Winning Colors took the lead from the start and never looked back. As the field rounded the track, she held off three determined challengers to win by a neck. With the victory, she became just the third filly in history to win the Kentucky Derby, marking the pinnacle of her career and exciting racing fans around the world. 

Mine That Bird (2009) 

Underdog stories don’t get much better than Mine That Bird’s in the 2009 Kentucky Derby. As a 50-1 longshot, he entered the race with little expectation of winning, only to capture an incredible victory in one of the most stunning upsets in racing history. 

After being bumped breaking from the gate, he settled into last place, trailing by a wide margin. As all eyes were on the leader of the pack, jockey Calvin Borel made his move, leading Mine That Bird along a legendary, rail-skimming ride as the field rounded the Final-Turn. In the last furlong, the pair surged past their competitors to win by nearly 7 lengths, proving that anything can happen in the Homestretch of the Kentucky Derby. 

American Pharoah (2015) 

While American Pharoah may not have been a longshot upset or a runaway winner, his 2015 Kentucky Derby victory marked the beginning of a historic chapter in thoroughbred racing. After a commanding performance at Churchill Downs, American Pharoah went on to accomplish what many believed we might never see again—a Triple Crown™ victory. 

He maintained the lead with ease during sloppy conditions at the Preakness Stakes, winning by 7 lengths. Then, all eyes turned to the 2015 Belmont Stakes as he led the pack over the 1.5-mile-long track. Despite competitors’ best efforts, American Pharoah crossed the finish line victorious, ending a 37-year wait for the sport’s most coveted achievement. Just three years later, Justify would follow in his footsteps, capturing the Triple Crown™ and adding another historic chapter to the modern era of thoroughbred racing. 

Each of these champions and many more have left their mark on the sport, creating stories that have endured long after they crossed the finish line. And with a new field of contenders arriving at Churchill Downs each May, the next chapter of Derby history is always waiting to be written.

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