Biggest Longshot Winners in Kentucky Derby History

Posted by Evan Chronis on Thu, Aug 8, 2019

While Country House made history as the first Kentucky Derby winner not to cross the finish line first at Churchill Downs, he also turned most of the betting world upside down with his victory. 

Kentucky Derby Longshot Winners

At 65-1 odds, Country House became the second biggest longshot to win the Kentucky Derby, giving the few true believers a nice payday after a memorable day at the track. 

With Country House now firmly planted in the oddsmakers' history books, here is a look at the five biggest longshot winners in Kentucky Derby history. 

Donerail (91-1)

Payout: $184.90

Horse racing was in a different stratosphere in 1913 compared to where the sport stands in the present day. While modern Derby fields typically comprise of 20 horses, the contenders in 1913 stood at eight. Even with the smaller field, Donerail came into the 39th 'Run for the Roses' with 91-1 odds. For reference, the largest odds in the 19-horse field in 2019  was at 65-1 for Country House.  

Even with the enormous odds against him, Donerail was able to take the lead down the final stretch after not leading before that point. In a last ditch effort as they closed towards the finish, Donerail moved past leader Ten Point to win the Derby and cement his place in history. 

Country House (65-1)

Payout: $132.40

Country House's historic Kentucky Derby run will forever focus more on the controversy than the odds, but he still goes down second on this list. Charging through on a rain-soaked and muddy track, Country House appeared to finish second behind then-undefeated Maximum Security. But minutes after the race concluded, the result was put under review as it was believed that Maximum Security impeded War of Will by merging into his lane illegally. 

After further review, Maximum Security was disqualified and second-place finisher Country House was declared the winner of the 145th Kentucky Derby. 

Mine That Bird (50-1)

Payout: $103.20

Most underdogs don't come into the Kentucky Derby and dominate the competition, but Mine That Bird wasn't like most horses. After trailing for a majority of the 2009 Kentucky Derby, Mine That Bird turned on the afterburners in the back half of the race, breaking past the rest of the field en route to a dominant 6 3/4 length victory. 

Giacomo (50-1)

Payout: $102.60

Four years before Mine That Bird wowed audiences at 50-1 odds, Giacomo accomplished the same feat in the 2005 Kentucky Derby. Instead of dominating the rest of the field like Mine That Bird, Giacomo turned in one of the most heart-stopping finishes in Derby history.

Seemingly stalled near the back of the pack for most of the race, Giacomo stuck to his gameplan, sticking to the far outside of the group instead of making his way near the rail. As the rest of the field trailed off, Giacomo maintained pace and outlasted the final two competitors to claim Derby glory. 

Gallahadion (36-1)

Payout: $72.40

Gallahadion entered the 1940 Kentucky Derby as a heavy underdog and for good reason. The West Coast horse didn't race well in the lead up to his trip to Churchill Downs and many believed that odds-on-favorite Bimelech was going to easily run away with the race. 

The steed didn't let the disappointment of recent performances affect him though, as he turned the race on its head and beat out Bimelech and the rest of the field with ease. 

Experience the 2020 Kentucky Derby with an Official Ticket Package

While longshot winners don't come around every year, history is still made at the Kentucky Derby on an annual basis. Don't miss out on the action next year when the 146th running of the Kentucky Derby kicks off. With over 30 different package options to pick from, make sure to attend the 2020 Kentucky Derby with Derby Experiences. 

2020 Kentucky Derby Official Ticket Packages