Top 10 Most Memorable Runnings of the Kentucky Derby

With its long and storied past, the Kentucky Derby has a history filled with unforgettable horses and performances. Gear up for Kentucky Derby 143 by reliving 10 of the most memorable editions of the Run for the Roses.

1933: Broker’s Tip

Broker’s Tip was far from the most accomplished winner of the Kentucky Derby; in fact, the Derby would mark the only race he ever won. But his name lives on thanks to an unforgettable battle between his jockey and the rider of runner-up Head Play—the two jockeys engaged in horseback fight down the homestretch, grabbing each other and striking with their whips in an effort to prevent the other from winning.

1957: Iron Liege

Iron Liege wasn’t supposed to win the Kentucky Derby. That feat was supposed to be achieved by his talented stablemate Gen. Duke, but when that runner had to scratch with an injury, Iron Liege proved to be a capable understudy. After taking the lead in the homestretch, Iron Liege was challenged by Gallant Man and appeared to be on his way to a runner-up finish, but when Gallant Man’s jockey misjudged the finish line and briefly stood up in the stirrups, Iron Liege battled back to win by a nose.

1973: Secretariat

In the 142-year history of the Kentucky Derby, no horse has come close to matching Secretariat’s record-breaking winning time of 1:59.40. The legendary “Big Red” was the first horse to win the Derby in less than two minutes, and only one horse since then (Monarchos) has done the same (1:59.97 in 2001).

1974: Cannonade

The 100th Kentucky Derby set a couple of notable records, including a still-standing record for number of entries—23 horses contested the centennial Derby! A then-record crowd of 163,628 turned out to watch Cannonade burst clear of the large field and win easily under Hall of Fame jockey Angel Cordero, Jr.

1987: Alysheba

Many Derby winners have won by bigger margins or posted faster winning types, but it’s unlikely that any have demonstrated more athleticism than Alysheba. While bidding for the lead at the top of the stretch, Alysheba clipped heels with front-running Bet Twice and stumbled, but instead of falling or losing his momentum, Alysheba picked himself up and re-rallied to win in an amazing performance.

1988: Winning Colors

In the history of the Kentucky Derby, only three fillies have prevailed, with the most recent being Winning Colors. A powerful gray filly with terrific early speed, Winning Colors ran away from her sixteen rivals early in the race and then held on gamely in the homestretch to win by a neck.

1997: Silver Charm

Few Derby winners have ever shown as much grit and determination as Silver Charm, who had a reputation for being impossible to defeat in a close homestretch battle. The gray colt needed every ounce of that determination in the 1997 Kentucky Derby, in which he edged favored Captain Bodgit to win by a head, the most recent photo finish in the Derby.

2002: War Emblem

It’s not easy to win the Kentucky Derby in gate-to-wire fashion, and in the years since Winning Colors only War Emblem has pulled it off. After being sold in the weeks before the Derby, War Emblem’s first start for his new connections proved to be a memorable one as he ran his Derby rivals off their feet to win the Run for the Roses by a decisive four lengths.

2009: Mine That Bird

As hard as it is to win the Derby leading all the way, it’s even harder to win after dropping back to last place early on… which makes it all the more remarkable that Mine That Bird rallied from last place to win the 2009 Kentucky Derby with one of the largest-ever margins of victory! Boldly ridden by Calvin “Bo-Rail” Borel, Mine That Bird miraculously passed the field on the inside to win at odds of 50-1, one of the biggest upsets in Derby history.

2015: American Pharoah

No list of memorable Kentucky Derbies would be complete without a mention of American Pharoah, who scored a hard-fought victory in 2015. His narrow triumph in the Derby served as a springboard to victories in the Preakness Stakes and Belmont Stakes, making him the first horse in 37 years to sweep the elusive Triple Crown.


About the Author

J. Keeler Johnson is a writer, blogger, videographer, and racing enthusiast who considers Zenyatta to be his all-time favorite racehorse. He is the founder of the horse racing website and a regular contributor to and