Biggest Kentucky Derby Underdogs in History

Sometimes, an unlikely competitor swoops in and takes the competition (and bettors bankrolls) by storm. Today, we look at the 5 biggest underdogs & upsets throughout Kentucky Derby history.

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The Kentucky Derby is one of the most prestigious horse races in the world and while often the favorite either wins or places at Churchill Downs, sometimes a big upset occurs. This happened in 2019 when Country House won the ‘Run of the Roses’ at odds of +6500.

Horse racing betting experts spend hours pouring over the race cards looking for the next big winner at the Kentucky Derby. And sometimes they strike gold. After all, since the first Kentucky Derby racing event took place in 1875 the favorite has won on just 51 occasions.

That’s a hit rate of 34.9% and suggests betting on the outsider is a genuinely viable tactics for punters looking to make big gains on the next race. Here are the five biggest winners in Kentucky Derby history…

Biggest Underdogs at the Kentucky Derby

All five of the Kentucky Derby underdogs below came into the race as big outsiders. In fact, some weren’t even mentioned by race commentators or in the newspapers before crossing the line. They have gone down in Kentucky Derby history for good reason, as we shall see.

5. Gallahadion, 1940: +3500

Gallahadion had Kentucky Derby pedigree through its dam Reigh Count, who won the 1928 race. But Gallahadion was overlooked in the betting odds when he lined up at Churchill Downs 12 years later. Owned by Milky Way Farm of Ethel Mars, Gallahadion wasn’t expected to challenge -250 favorite Bimelech here.

Gallahadion and Jockey Carroll Bierman at kentucky derby in 1940

Trainer Roy Waldron holds on to the bridle with Jockey Carroll Bierman on winner Gallahadion during the Kentucky Derby in Louisville on May 4, 1940. (AP Photo)

But Gallahadion caused a major upset by lurching in front along the rail and beating Bimelech by more than a length. Sadly for his owners, Gallahadion couldn’t convert the Kentucky Derby win into victories in the Preakness Stakes and Belmont Stakes, but did earn plenty of punters a big payout that day in Kentucky.

4. Giacomo, 2005: +5000

Sometimes the favorite isn’t in the picture as the horses cross the line at the Kentucky Derby and this is exactly what happened in 2005. Giacomo was battling another outsider in Closing Argument for the win in the final yards of the race, with early favorite Bellamy Road well behind the lead.

Jockey Mike Smith successfully pushed Giacomo over the line to claim victory. The race commentator that day hadn’t even mentioned Giacomo until the last two seconds of the race – and plenty of punters missed out on the chance to back him.

3. Mine That Bird, 2009: +5000

Four years after Giacomo’s heroics Mine That Bird would match the feat with another +5000 triumph. Calvin Borel skimmed the rail as the jockey forced his ride through the pack on a rain-drenched day at Churchill Downs.

calvin borel rides mine that bird across finish line at 135th kentucky derby 2009

Calvin Borel rides Mine That Bird across the finish line during the 135th Kentucky Derby horse race at Churchill Downs. (AP Photo/Al Behrman, File)

What was so spectacular about the upset was the distance Mine That Bird won by. Over 153,000 fans watched him claim victory by over six lengths – a remarkable achievement considering the strong field.

What’s more, even on the sloppy track Mine That Bird passed the line in 2:02:66 – one of the fastest times in those confusions ever recorded.

2. Country House, 2019: +6500

A decade on from Mine That Bird and it was time for Kentucky Derby racing experts to hold their breath once again. Trainer William I. Mott had never won the Kentucky Derby when he sent out Country House and jockey Flavien Prat. Country House was one of the last horses to load into the traps and was in fact second to cross the line.

Maximum Security and country house cross kentucky derby finish line

Luis Saez on Maximum Security (R) crosses the finish line against Flavien Prat on Country House during the 145th running of the Kentucky Derby. Country House was declared the winner after Maximum Security was disqualified after a review by race stewards. (AP Photo/Matt Slocum)








In another sodden race at Churchill Downs, the winner Maximum Security became only the second in history to be disqualified post-race. The stewards looked back at the race and determined Maximum Security had forced other horses to steady on the final curve.

After a 15-minute wait, it was announced Country House was the default winner following Maximum Security’s disqualification.

1. Donerail, 1913: +9100

For more than a century Donerail has reigned supreme as sparking the biggest upset in Kentucky Derby history. The horse was bred and trained in Kentucky but was thought to have little chance of challenging the favorites when the horses lined up for the race in 1913.

Jockey Roscoe Goose, who would go on to win the Bashford Manor Stakes, Louisville Cup and Kentucky Oaks during his racing career, was a 21-year-old novice when he rode Donerail to glory.

Donerail’s victory remains the biggest upset to this day and his owners received a $5,475 payout – the equivalent of $146,000 today.

Riders up! Read our Kentucky Derby betting guide for the latest odds & best books to bet on the Kentucky Derby.

James Guill

James Guill is a former professional poker player who writes fro about poker, sports, casinos, gaming legislation and the online gambling industry in general. His past experience includes working with IveyPoker, PokerNews, PokerJunkie, Bwin, and the Ongame Network. From 2006-2009 he participated in multiple tournaments including the 37th and 38th World Series of Poker (WSOP). James lives in Virgina and he has a side business where he picks and sells vintage and antique items.

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