The Kentucky Derby, known as “The Most Exciting Two Minutes in Sports,” is filled with moments that have left an indelible mark on racing history. From astonishing upsets to record-breaking victories, here are the top 10 moments that have come to define this legendary event.
1. Secretariat’s Unbreakable Record (1973)
In 1973, Secretariat didn’t just win the Kentucky Derby—he redefined greatness. Finishing the race in a blistering 1:59 2/5, he set a record that still stands today. Secretariat’s performance was a prelude to his historic Triple Crown, solidifying his status as one of the greatest racehorses of all time.
2. Aristides Wins the First Derby (1875)
The Kentucky Derby’s rich history began with Oliver Lewis riding Aristides’ to victory on May 17, 1875. Competing against a field of 15 horses, Aristides claimed the inaugural Derby, forever marking the start of what would become America’s longest-running annual sporting event.
3. Donerail’s Unbelievable Upset (1913)
In 1913, Donerail delivered the biggest shock in Derby history by winning at staggering 91-1 odds. His unexpected victory reminds us all that the Derby is a race where anything can happen, and long shots can defy the odds in spectacular fashion.
4. American Pharoah Ends the Triple Crown Drought (2015)
After 37 years without a Triple Crown winner, American Pharoah’s 2015 Derby win was a moment of pure exhilaration. His victory at Churchill Downs was the first step in his historic Triple Crown triumph, a feat that united racing fans and captured the world’s attention.
5. Barbaro’s Triumph and Heartbreak (2006)
Barbaro’s dominant Derby win in 2006 showcased a horse destined for greatness. However, just two weeks later, tragedy struck when he sustained a life-threatening injury at the Preakness. Barbaro’s courageous battle for survival captivated the nation, turning his story into one of both triumph and sorrow.
6. War Admiral and Seabiscuit’s Epic Rivalry (1938)
War Admiral’s 1937 Derby victory set the stage for an epic rivalry with Seabiscuit, culminating in their legendary match race in 1938. Though their rivalry is best remembered for that epic showdown, War Admiral’s Derby win remains a key moment in racing history.
7. Regret Shatters Barriers (1915)
In 1915, Regret became the first filly to win the Kentucky Derby, a groundbreaking achievement that challenged the status quo. Her victory paved the way for future fillies, proving that gender was no barrier to success in the most prestigious race in the world.
8. Bill Shoemaker’s Brilliant Ride on Swaps (1955)
Legendary jockey Bill Shoemaker delivered a masterful performance in 1955 when he guided Swaps to a stunning victory over the heavily favored Nashua. Shoemaker’s skill and strategy turned this race into one of the most memorable moments in Derby history.
9. Winning Colors Stuns the Field (1988)
In 1988, Winning Colors defied expectations and became only the third filly to win the Kentucky Derby. Her powerful performance against a field of colts demonstrated her strength and determination, securing her place in the annals of Derby history.
10. Grindstone’s Nail-Biting Photo Finish (1996)
The 1996 Derby delivered one of the most thrilling finishes ever when Grindstone edged out Cavonnier by a nose in a photo finish. The race was a heart-pounding spectacle that kept fans on the edge of their seats and remains one of the closest finishes in Derby history.
Greatest Two Minutes in Sports
The Kentucky Derby is more than just a horse race—it’s a tradition, a celebration, and a stage for the extraordinary. These top 10 moments have not only defined the Derby but have also become timeless stories of courage, skill, and the thrill of competition. As each year passes, new moments are added to this storied history, reminding us why the Kentucky Derby continues to captivate the world.
