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Kentucky Derby Betting Strategy: 5 Tips for Picking a Winner in 2024

Mitchell South

by Mitchell South

Updated May 16, 2024 · 7:33 AM PDT

Horse racing takes place nearly every day of the year. However, the Kentucky Derby (also known as the Run for the Roses) without a doubt draws the most attention, fanfare, and betting volume of any other event on the horse racing calendar.

The Kentucky Derby is run on the first Saturday in May at Churchill Downs in Louisville, KY. If you’re wondering how to pick a winner for the biggest horse racing event of the year, you need to understand what makes the Derby different than all other races.

Our guide to picking a winner covers the race’s key dynamics and points out specific factors you need to consider when formulating the best Kentucky Derby betting strategy.

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Kentucky Derby Online Betting Strategy – 5 Key Tips

With many options comes great opportunity. It is difficult to parse 20 horses and predict who will bow to pressure. Betting the Derby is no doubt a challenge, but it’s a lucrative one if you’re successfully able to pick the winner.

In addition to normal handicapping strategies such as closely examining each horse’s most recent races, and trying to determine how the race will be run (who will be ahead early, who will look to rally from behind), there are five strategies unique to the Kentucky Derby that are worth your close consideration as you try to select a winning race horse.

Derby Tip #1: Consider the Pace of the Races

The pace of any race is important. If the early leader is able to go slowly and exert little effort, there’s a good chance he’ll save energy and have enough kick left to go wire-to-wire late in the race. Conversely, if there is a speed battle in the early going, the front runners are likely to get tired. As such, this sets up horses who have something left in the tank down the stretch.


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Because the Kentucky Derby has 20 horses, it is very rare for a horse to get loose on the lead.

There are always amped up horses who go out aggressively but end up falling out of position. However, taking it really easy early on and having to pass 17 or 18 or 19 horses is challenging. It is exceptionally difficult to find racing room and avoid going too wide if you are too far behind.

Kentucky Derby winners are very often those sitting in a good position just off the pacesetters. When evaluating potential winners, look for tactical speed. You want a horse with enough of an engine to keep up and be in a good spot, but should avoid those known for front-running, early speed that is difficult to harness and maintain throughout the race.

Derby Tip #2: Stamina Matters

The Kentucky Derby is a 1.25-mile race. It’s key to recognize that the Derby is the longest race that most, if not all of the contenders have ever been in.

Look for horses that prefer distance races to sprints.

Consider how the field has adapted to previous changes in distance, and take close note of their bloodlines. If mom and dad were adept at longer races, it’s a good sign that a given horse has a good chance to fair well in the Kentucky Derby.

Derby Tip #3: What Class Are Horses From?

Some contenders will be more battle-tested than others. Consider who horses have raced against previously, and how they have fared.

For example, winning at smaller tracks against lesser competition is not as impressive as beating the best horses at the top venues.

The Derby is the biggest event of all, and experience often matters when performing on the largest stages. 

Derby Tip #4: Don’t Ignore the Jockeys!

When looking for a Kentucky Derby winner, fans tend to focus on the horses. But those who ignore the jockey do so at their own peril, as there’s generally much more info available about their strengths and weaknesses compared to the horses they’re racing.

The three-year-old horses running the Derby all have a limited track record. Some have run as few as two or three races in their life. None have competed in a race as long or with as many entries at the Kentucky Derby,

Meanwhile, the trainers and jockeys racing these horses tend to be the same people year in and year out, so it’s much easier to judge their past performances. Considering which humans have  consistently raced successful horses is worthwhile.

Whether it be owners, trainers, or jockeys, they have a much longer resume to examine than the horses themselves.

Derby Tip #5: Favorites Have Dominated, but Underdogs Are Coming Back

For a five-year stretch, favorites dominated the Kentucky Derby. During the five runnings from 2014 to 2018, the average payout on a $2 win bet was $8.12, with the highest-priced payout in that period just $11.40 (Always Dreaming, 2017).

However, more recently, underdogs have prevailed. Long shot Country House was declared the winner in 2019 after Maximum Security was disqualified, resulting in a win bet payout of $132.40! Last year, Authentic produced an upset with a payout of $18.80.

Taking note of Key Derby Betting Trends is a great final step when picking a Kentucky Derby winner.

What Type of Bet Should You Make?

While win bets are the simplest horse betting option to understand, alternative straights bets include place bets and show bets.

Neither pay as much as a win bet, but there is a greater chance to cash these types of gambles. Wagering to place means your horse must finish first or second in order for you to cash a ticket. A show bet requires the horse you select to finish in the top three in order to win your wager.

More advanced bet types available in horse racing include exacta, trifecta, and superfecta bets. These bet types are much more difficult to win, but for experienced handicappers, greater risk brings greater reward. To understand these a little better, we’ve taken the liberty of breaking them down for you.

Exacta Bet

An exacta bet is a wager where you select the first and second place horses in the exact order you think they will finish. For the 2024 Kentucky Derby, you might choose Dornoch and Sierra Leone to place first and second respectively and, if they do, you win your bet.

Trifecta Bet

A trifecta bet is a wager where you select the first, second, and third place horses in the exact order you think they will finish. For the 2024 Kentucky Derby, you might go with Dornoch, Sierra Leone, and Mystik Dan to place first, second, and third respectively. If these three horses finish in the order you predicted, you win your bet.

Superfecta Bet

A superfecta bet is a wager where you select the first, second, third, and fourth place horses in the exact order you think they will finish. This is likely the most challenging type of wager to make since it requires you to land four horses in the right placing. For the 2024 Kentucky Derby, you might bet on Dornoch, Sierra Leone, Mystik Dan, and Catching Freedom to place first, second, third, and fourth respectively. Nailing the right order for all four of the top horses wins your bet.

Is Picking a Derby Winner Different from Other Races?

While Churchill Downs is a historic venue for horse racing, it sits empty for the vast majority of the year. Of course, this all changes on Kentucky Derby day, as over 100,000 people flock to the track to take in the highest-profile race of the year and try their hand at projecting a Derby winner.

Let’s delve into what makes this race bigger than all others.

A Brief History of the Kentucky Derby

The Kentucky Derby has been run since 1875.

A laundry list of the greatest horses of all time have won the Kentucky Derby. Secretariat, the fastest thoroughbred in history, prospered in a record time in 1973. The previous mark was held by champion Northern Dancer in 1964. War Admiral, Whirlaway, Citation, Seattle Slew, Affirmed, and American Pharoah all were first across the finish line in Louisville.

The combination of longstanding traditions and the history of elite participants provides the Kentucky Derby with its prestigious reputation.

Understanding the elite level of competition present is the first key thing to keep in mind when looking for a winning horse at the Derby.

The Kentucky Derby Is a Component of the Triple Crown

Winning the Triple Crown is one of the greatest accomplishments in all of sports. As such, it’s no wonder that the Triple Crown generates so much attention with the horse racing community. Winning the Triple Crown requires a three-year-old horse to win all three races, which are all races at different distances at separate times over a five-week span.

The Kentucky Derby is the first of three racing legs of the Triple Crown series. Two weeks later the Preakness Stakes takes place in Baltimore, followed by the Belmont Stakes in New York.

More Horses Participate Than Normal

Most horse races have somewhere between 5 and 10 runners. The Kentucky Derby is significantly larger, welcoming an elite crop of 20 entrants.

A series of prep races that help identify the fastest three-year-old horse in the lead up to the Derby. This ensures that all of the top contenders get a spot come Derby Day.

Finding an edge within such an elite group of competitors isn’t easy, but there are certain factors and trends worth paying attention to when handicapping the race.

The Kentucky Derby Is Chaotic

Like all sports, horse racing involves a significant degree of luck. When more obstacles to victory are present during a race, the harder it is for bettors and fans to accurately predict the outcome and successfully pick a winner.

If you have 20 horses racing, it’s almost inevitable that someone is going to get bumped or jostled. While you see this from time to time in horse racing, it is a near certainty in the Kentucky Derby. It’s yet another element that makes the race consistently unpredictable.

With more horses on the race track, it’s likely that some horses will get stuck behind a wall of equine (created by the sheer volume of horses on the track) and have no room to get around after the race’s initial stages.

Others will be forced to run wider than normal, because not every entrant gets to sit right along the rail and save ground on the turns. With such a high density of animals racing, it often creates traffic problems.

If racing wasn’t a big enough problem, the weather is notoriously up in the air on Derby Day. This means that the track conditions can change in a hurry. If it pours rain, you can expect the dirt surface to turn to mud, drastically altering the complexion of the race.

Even if a horse is the best in the world racing on a certain surface, that doesn’t necessarily imply that they’ll be able to translate that to such radically different conditions. Sometimes a big longshot loves the mud.

Pay attention to the weather conditions and size of the field in past races when determining a horse’s chances of winning the Kentucky Derby. 

What to Expect From the Overall Environment

Horses feel pressure and so do their human connections (jockey, trainer, owner). Different people and horses react to stress in varying ways, and the Kentucky Derby is definitely one of the most stressful events on the racing calendar.

When tension is high people often make mistakes. A trainer could work his horse too hard or not hard enough leading up to the big race. A jockey could make a move too early or wait until it is too late to get his horse moving at its fastest down the stretch. Whether it be an error in riding or training, mistakes tend to happen when tension is high.

Some derby horses suffer from the long walk to the starting gate, waiting for 19 competitors to get situated, and the defining noise of a massive crowd. Others thrive under those conditions.

Take note of both a jockey and horse’s past ability to perform in high-pressure environments when sizing up the competition on Derby Day.

Kentucky Online Sports Betting

The Kentucky Derby isn’t the only way to enjoy wagering in the Bluegrass State. Kentucky online sports betting is now live and some of the best sportsbooks on the market serve rookie sports bettors and seasoned sharps.

Sportsbook Kentucky Sportsbook Details
DraftKings DraftKings Kentucky
FanDuel FanDuel Kentucky
Bet365 Bet365 Kentucky
BetMGM BetMGM Kentucky
Caesars Sportsbook Caesars Sportsbook Kentucky

While there may not be any major league sports teams located within the borders of the Bluegrass State, Kentucky sports betting apps get you closer to all the action in your favorite games. Kentucky sports bettors can use these sportsbook apps to wager on any of their favorite teams, including NCAA college sports teams. Hit the links in the right side of the table for more information on the best Kentucky sports betting apps and sign-up today while you wait for the next Kentucky Derby.

Kentucky Derby Betting Strategy FAQ

What factors should I consider when developing a Kentucky Derby betting strategy?

There are a number of different factors to consider when developing a Kentucky Derby betting strategy including the pacing and stamina of horses as well as jockey experience.

How do I determine which horse to bet on in the Kentucky Derby?

You can do research to see which horses are favored to win and also look into their trainers and jockeys for the level experience they have as well.

What is the best type of bet to place on the Kentucky Derby?

Exacta, trifecta, and superfecta bets are the best types of bets you can make on the Kentucky Derby.

How important is a horse's jockey when making a Kentucky Derby bet?

Jockeys are important and their level of experience also matters for a race like the Kentucky Derby.

Should I bet on multiple horses in the Kentucky Derby, or focus on just one?

It depends on the type of bet you make. You can make a regular bet to wager on the winning horse or you can make bets on multiple horses as well.

How can I use past performances to inform my Kentucky Derby betting strategy?

It can be challenging to use past performances to bet on the Kentucky Derby since there are so many different horses competing. That said, research is always key and can give you a rough idea of where certain horses are at.

How do I manage my bankroll effectively when betting on the Kentucky Derby?

Make sure you always bet within your means and try to find horses that will give you value on your return.

Are there any longshot horses that might be worth betting on in the Kentucky Derby?

Tapit Jenallie, Gin Gin, and Lemon Muffin are all potential longshots that could win the 2024 Kentucky Derby.

Bet to Win!

Keep track of the futures odds on Derby top contenders and sign up for a horse racing sportsbook app so you can bet on the horses on race day!  Also, for a more in-depth looking into this race, check out our how to bet on the Kentucky Derby  guide and Kentucky Derby odds.

While we can’t pick the winner for you, hopefully, learning the methods of sports betting will point you in the right direction. Betting on sports is great fun and can be profitable if approached in a thoughtful way.

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