How Much Would You Win On Kentucky Derby? $5 Bettor Won $1000+ Last 10 Years

Fact Checked by Thomas Leary

The Kentucky Derby is unlike any other horse race in the United States. While most races are limited to 14 entries, the Derby features a field of up to 20. Many, if not all, of the horses will run 1-1/4 miles for the first time, and they’ll do that before one of the largest crowds gathered to watch a live sporting event all year.

It’s critical to understand all of that when you’re handicapping the Run for the Roses. In some ways, it’s like 20 ping-pong balls in a drawing machine. The outcome, as you can see from the table below, can be totally random.

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Kentucky Derby Winnings Explained

Winning Horse


Money Won On $5 Bet




Rich Strike



Medina Spirit*






Country House






Always Dreaming






American Pharoah



California Chrome






Yes, there will always be a horse or two in the field who, talent-wise, are heads and shoulders above the rest, but they could start poorly, get behind a large pack of horses and be unable to make a move down the stretch. Or think of a horse like Epicenter, who two years ago ran a brilliant race and was just a few strides away from winning as the 4-1 favorite, only to see Rich Strike come from nowhere to stun everyone as the longest shot on the board hit the wire first.

If you were to have bet $5 to win on each of the past 10 Derby winners, you would have walked away with $1,036.05, a nearly 20-fold return on your $50 total investment. Not bad for anyone familiar with Kentucky betting apps.

How To Pick Your Kentucky Derby Horse(s)

That said, it’s worthwhile to review horses’ past performances, study their racing styles, consider their starting positions and factor in their betting odds when picking your horse. 

Not that long ago, the betting favorite won the Kentucky Derby six years in a row. It would have been seven years had Maximum Security not been disqualified in 2019. But in most cases, even the favorites have value. Typically, the betting favorite in a horse race has odds of 2-1 or shorter, but odds that short are rare in the Derby.

Another thing to keep in mind is that unlike sports betting, which is fixed-odds, wagering on horse racing is parimutuel. That means the odds will change as more money enters the betting pools. You may place your bet when a horse’s odds are 5-1, but you’ll get the odds posted when the race starts. So, your potential payout may rise or fall.

If you find yourself liking two or more horses while handicapping the race and can’t really decide on one, consider placing an exotic wager, like an exacta or trifecta. Exactas and trifectas are like parlays. In an exacta, you’re betting on a horse to win and another to finish second. A trifecta bet is on horses to finish first, second and third. You can also box horses to cover several combinations.

With an exacta or trifecta, you can make smaller wagers with the potential for larger payouts. Last year, the exacta paid $330.44 on a $2 bet, and the winning trifecta paid $491.18 on a 50-cent bet.

Where To Wager On The Kentucky Derby

Depending on where you like, there are numerous ways to bet on the Derby and other races taking place at Churchill Downs and elsewhere on Derby Day. Kentucky has eight approved advanced-deposit wagering platforms, and those platforms may have agreements in place with other operators.

For example, DraftKings Kentucky partners with Churchill Downs’ TwinSpires for its DK Racing app.

If you don’t have an ADW account, setting up one is about the same as setting up an online sports betting account, and new users may qualify for promotional bets or deposit matches. Bettors with a FanDuel sportsbook account can easily connect to FanDuel’s racing app and use the same wallet to wager on races.

Keep visiting for more analysis on Kentucky Derby 150 and the latest sports betting news coming from the Bluegrass State.

Also of interest: The Most Successful Jockeys In Derby 150.


Steve is an accomplished, award-winning reporter with more than 20 years of experience covering gaming, sports, politics and business. He has written for the Associated Press, Reuters, The Louisville Courier Journal, The Center Square and numerous other publications. Based in Louisville, Ky., Steve has covered the expansion of sports betting in the U.S. and other gaming matters.

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