Biggest Kentucky Derby Wins Ever Using Superfecta Payout Calculator

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The biggest Kentucky Derby results through history, with a focus on Superfecta payouts, Trifecta payouts, and Exacta payouts.

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The Kentucky Derby is the highlight of May’s sporting calendar. Commonly known as “the most exciting two minutes in sports,” the race takes on another level of excitement for sports bettors.

Horse racing has long been seen as separate from sports wagering. But, with the popularization of the latter, Americans are becoming more interested in the big races as well. And with 20 horses in the field, races don’t get much bigger than Kentucky’s “Run for the Roses”.

Kentucky Derby Biggest Wins

There are two main outcomes that get the public’s excitement; a powerhouse horse wins at Churchill Downs, starting a potential run to a Triple Crown, or a big underdog pulls the upset, leading to big payouts for wagers at the track and off-site.

We’ll focus on the second one today – the largest betting wins in Kentucky Derby history.

Past 10 Years of Kentucky Derby Winners, Plus Exotic (exacta, trifecta, superfecta) Payouts

First, some basics. A “win” bet is as easy as it sounds. You bet on a specific horse to win. If he/she does win, you win!

But, what is an exacta, a trifecta, and a superfecta?

ExactaYou’ll need to pick the first- and second-place horses in the correct order to cash your ticket.
TrifectaSelecting the first, second, and third place finishers in order.
Superfecta1-2-3-4 finishers in order.

As you can imagine, payouts increase as the number of horses selected does likewise.

Past Winners & Payouts

All results below are based on a $2 bet, using our exacta payout calculator, trifecta payout calculator, and superfecta payout calculator.

In other words if you bet $2 on the horse to win, or placed a $2 wager on the exacta, trifecta, or superfecta, this is what you’d have won:

YEARKENTUCKY DERBY-WINNING HORSE AND PRICEEXACTA PAYOUTTRIFECTA PAYOUTSUPERFECTA PAYOUT
2021Medina Spirit* ($26.20)$503.60$3,393.80$18,912.80
2020Authentic ($18.80)$41.00$2,623.60$15,851.60
2019Country House ($132.40)$3,009.60$22,950.60$102,800.20
2018Justify ($7.80)$69.60$282.80$39,236.40
2017Always Dreaming ($11.40)$336.20$16,414.40$151,949.00
2016Nyquist ($6.60)$30.80$346.80$1,084.20
2015American Pharaoh ($7.80)$72.60$404.00$1,268.20
2014California Chrome ($7.00)$340.00$6,849.20$15,383.80
2013Orb ($12.80)$981.60$13,851.20$57,084.00
2012I’ll Have Another ($32.60)$306.60$3,065.60$96,092.80

Well, we were all thinking it. Imagine getting it right in 2017 or 2019.

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Biggest Exacta, Trifecta Payout in the Past 10 Years: 2019

The 2019 Kentucky Derby was one of the most memorable races in the event’s history for horse racing enthusiasts and bettors alike.

A crowd of over 150,000 turned out for a beautiful spring day – only to see the skies open about an hour before race time. Track conditions turned sloppy.

The favorite, Improbable, was never a big factor and would finish fifth, but the drama came with the #2 choice, Maximum Security who roared to an early lead and crossed the finish line first. However, in attempting to hold off the other contenders, Maximum Security impeded the paths of three other horses.

After a lengthy review, Maximum Security became the first-place hose in Kentucky Derby history to be disqualified for an on-track infraction. Second-place finisher Country House – a 65:1 longshot – was moved into first place, and all other top-15 finishers moved up by one spot.

Trifecta Payout Calculator Kentucky Derby

The Result?

At those 65:1 odds, Country House paid $132.40 on a $2 bet – the largest Kentucky Derby ‘win’ payout since Donerail paid $184.90 all the way back in 1913.

But moving into the exotic category meant even larger payouts. The combination of Country House and new second-place finisher Code of Honor (15:1 odds) meant a $2 exacta bet paid out over $3,000. Well, $3,009.60 to be exact. Add in third-place Tacitus (6:1) and a $2 trifecta meant a win of almost $23,000.

Historically, it was the second-biggest payday in Derby history (we’ll get to #1 soon). But even though a $2 superfecta ticket paid over $100K, it still fell short of the superfecta just two years prior.

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Biggest Superfecta Payout in the Past 10 Years: 2017

When you see the 5:1 odds for 2017 champion Always Dreaming, your mind may not trigger thoughts of an enormous payout. But that’s the beauty of exotics wagering – it’s not only about the winner.

In this case, it was about the second and third-place finishers, Lookin at Lee and Battle of Midway. These two horses went off at odds of 33:1 and 40:1 respectively.

When combined with fourth-place finisher Classic Empire – the horse that started the day favored to win the Derby – it triggered a superfecta of over $150,000 ($151,949.00) on an investment of only $2. Talk about maxing out the Superfecta payout calculator!

Superfecta Payout Calculator

The race was a great example of how one or two longshots can turn an otherwise predictable finish into a bonanza for Kentucky Derby bettors. But even so, it paled in comparison to the most profitable Derby of all time.

The 2005 Kentucky Derby: Who Wants to be A Millionaire?

The race to remember for horse bettors everywhere occurred 17 years ago on a picture-perfect day at Churchill Downs. Trifecta payout paradise.

Bellamy Road, Afleet Alex, and Bandini were the picks of many experts, but it was the entry of a 71:1 longshot that would change this race.

Spanish Chestnut was no one’s pick to win the Derby, but he did have a well-earned reputation for fast starts. The Derby was no different, as Spanish Chestnut tore through the first half-mile in 45 seconds. This caused the favorites to expend great energy in keeping pace.

Longshots Step Up

But patiently sitting near the back were longshots Giacomo (50:1) and Closing Argument (72:1). As the race wore on, Spanish Chestnut (and the frontrunners) wore down, allowing these two longshots to stalk the pace, joining Afleet Alex for a tight finish that saw Giacomo pull the major upset, with Closing Argument second and Afleet Alex third.

Joining the party to close out the superfecta was 29:1 shot Don’t Get Mad. The name was appropriate for bettors who managed to choose the 10-18-12-17 superfecta, which would shatter track payout records.

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When the dust settled, history was made:

Win

At $102.60, Giacomo was at the time the highest-paying winner since Donerail in 1913 (although 2019’s Country Road and 2009’s Mine That Bird have since surpassed his mark).

Exacta

The combination of Giacomo and Closing Argument paid an unthinkable $9,814.80 on a $2 bet.

How uncommon is this? Only five Kentucky Derbys have seen exacta payouts of $1,000 or more, and the second highest amount (2019) is less than a third of the amount of the 2005 wager.

Trifecta

Afleet Alex’s odds were fairly short at 9:2, but was still enough to create the only six-figure trifecta payout in Derby history at $266,269.60. Remember, all these figures are based on a $2 bet. Many horse bettors limit their trifecta wagers to $1 – still a pretty nice return.

Superfecta

This is where the numbers really explode. At odds of 29:1, Don’t Get Mad’s fourth-place finish combined with the top-three finishers to create a life-changing superfecta payout of $1,728,507!

It’s going to be hard to duplicate 2005 – but the beauty of horse racing is that longshots do win. Quite often, in fact. And when wagering on exactas, trifectas, and superfectas, it’s not only about the winner!

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