Triple Crown Betting Sites

Updated April 9, 2024

The Triple Crown is the most prestigious and difficult title to achieve in American horse racing. It can either refer to the three biggest horse racing events in America: the Kentucky Derby, Preakness Stakes, and Belmont Stakes or the title for the horse who wins all three. Only 13 horses in almost 150 years have achieved this glorious feat. Triple Crown betting sites are open all year round ready to cater to all players in for the ride.

Let’s look at what we’ll cover with the Triple Crown:

Best Triple Crown Betting Sites

SportsInteraction (SIA)


SportsInteraction is a one-stop-shop for many Canadian bettors and offers strong selections of betting odds including the Triple Crown with solid betting lines across.


SIA will match a 100% initial deposit bonus up to $200.

It isn’t one of the most reputable online sportsbooks in Canada for nothing. You can’t go wrong with SIA as one of your main books with its strong selection of odds, a wide variety of betting markets, and a competitive signup offer.

Read Sports Interaction Review



Bet365 has a dizzying amount of betting markets with competitive betting odds and a rich selection of props. In fact, it could be argued they have everything.


Win up to $200 in cash value when you deposit $200 or more with Bet365.

A popular online sportsbook even outside Canada, Bet365 is recommended for all levels of players. It may take newbies a while to be familiar with the interface, but with a little diligence, you can find any type of betting market here including anything from the Triple Crown.

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Betway offers a ton of betting odds at great value from every notable horse racing event including the Triple Crown of course. It also features plenty of props.


Betway matches 100% of initial deposits up to $250 in free bets.

An online sportsbook that is quickly and steadily growing in popularity, Betway offers two unique features to set it apart: the in-game ticket cash out option and the Plus Loyalty Club, which literally pays players to play. Add its nifty betting platforms and it’s sleek choice.

Read Betway Review

Triple Crown betting picks

Understanding Triple Crown betting sites begins with understanding how its betting odds and its betting markets work. Odds are a translation of implied probability. It’s a system designed to reward profit based on the likelihood of success: the more likely a winner, the lesser the profit.

Odds are usually seen in American format: with a plus and minus. The plus indicates how much you win on a $100 wager while the minus is the opposite: how much you have to bet to win $100. When it comes to horse racing, you may see more plus-odds in picking winners due to the difficulty of winning a race and the sheer amount of contestants.

This is a time to utilize your risk assessment instincts. Of course, a likelier winner yields less profit because it is more predictable. A longshot, or an underdog, will yield more profit because the risk is higher. 

Some bets can seem easy, even safe almost. But there is no such thing as a “sure bet” as some of the biggest horse racing upsets have shown. Even Secretariat’s record, which has stood for nearly half a century is bound to fall.

It all depends how much you are comfortable risking. Plenty of sharks will gladly throw a couple of thousand to win a few hundreds while some play the lottery betting lunch money in hopes of scoring big. As long as you have a budget and know your limits, you can pick your own goal.

Triple Crown betting preview

To understand Triple Crown betting sites, first get to know the Triple Crown a bit more intimately. Each of its three jewels: the Kentucky Derby, Preakness Stakes, and Belmont Stakes all have their own identities and are all separate major horse races.

The popularity of horse racing betting has not waned over time. In fact, it’s become even bigger with all three races setting and breaking various betting records in the last few years. As sports wagering becomes more of a norm in North America, expect this to keep trending up.

This might mean more betting markets opening in Canada, where horse racing is a staple among bettors.

There are endless betting markets with the Triple Crown and it can be overwhelming even for experienced players. The key is to narrow down your focus and identify what you are betting for. Some players bet solely for the thrill. Some want to profit. Where would you fit in?

Let’s take two players: Sam the Shark and Curt the Casual. 

Sam has invested tens of thousands into horse racing betting. He’s had weeks where he’d lose thousands but also some where he’d win thousands. All-in-all, Sam has won a couple of grand but he’s staked over ten times the amount.

Either way, winning a cool thousand or two is still winning. It may have taken Sam more intensive researching, some sleepless nights, and lots of double face-palming, but he has successfully profited off of Triple Crown betting. 

Curt is a bit more laidback. He’s the type who would “throw darts” at some of the biggest payouts around. He loses a lot more than he wins. In fact, his success rate is probably less than 10%. That means for every 10 bets he makes, he wins less than once. 

Like a lottery player, Curt faces significantly more disappointments than successes. But once in a while, Curt is going to hit it bag just like he did when he bet on Sarava to win the Belmont Stakes at a whopping 70-1 odds. He watched his $100 bet blow up to over $7,000.

Are you more of a Sam, a tactician who makes money by spending money, or a Curtis, who likes to play the lottery? Either way, you will need to do research, temper expectations, and keep within a budget.

What can you bet on during the Triple Crown?

A better question is: what can’t you bet on during the Triple Crown? This depends on the Triple Crown betting sites. Sometimes, depending on how much hype there is, you can bet on even the most trivial props for the Kentucky Derby. This most prestigious horse race is what carries the brunt of the betting markets for the Triple Crown.

The Kentucky Derby is rich with props and online sportsbooks pull out their best betting odds in hopes of getting a chunk of the betting action. But the Preakness Stakes and Belmont Stakes also offer most of what the Derby offers, save for the props.

Triple Crown Winner 2020

For all three of the Triple Crown jewels, the main betting odds is who will win the horse race. These are usually the first odds to be released and the ones that are maintained most. 

But before the Kentucky Derby, there could be betting odds on if a particular prized horse will win the Triple Crown. This continues until the horse in question loses one of the races or is scratched. 

It is also possible for a less-than-hyped horse, who wins the Kentucky Derby impressively to have betting lines opened on if it could win the Triple Crown.

For obvious reasons, the horse needs to win all three races for the bet to cash. If you are siding with a horse to win the Triple Crown, you can bet four times: one for it to win the Triple Crown and one for each race it will win. 

You may even be able to parlay these bets: put them all together under one bet to increase your payout to immense odds!

Podium finish

At most Triple Crown betting sites, outside of picking the outright winner, picking the podium finish for each individual contest is the next betting market to scrutinize. You get to pick, per horse, what position they will finish in within the top three: to win (first place), top 2 (first or second), or top 3 (first, second, or third). Just like the prize money, the payout decreases the lower you go.

In some cases, you may even be able to bet on a horse to “not finish in the podium”. These odds could be either very high or low depending on the horse. Prized horses or contenders could return significant payouts as it would be a bold call to pick them to miss the podium. But the return on underdogs could be minimal if anything at all.

Betting on the podium finish could be more profitable than betting outright. Horse racing can be unpredictable and even Triple Crown threats tend to underperform or get upset. So much can change by the time the gun is fired. 

Triple Crown – prop bets: events, horses, jockeys etc. 

The Triple Crown races offer a glut of prop bets and the Kentucky Derby is the leader with these. Depending on the year, if there is a prized horse or multiple ones, and if the media hype and fan attention are hot, the props can be bountiful.

But on this note, prop bets tend to be 50/50 with a few exceptions. Some props appear to be arbitrary e.g. the starting letter of the winning horse’s name, the winning horse wearing blinkers or not, the margin of victory, but oddsmakers have invested plenty of time and resources to calculating these (a computer usually does).

Before betting on props, even if just for fun, do a little bit of research to see if there are any trends

Here are some examples of popular prop bets you may find at Triple Crown races, mostly with the Kentucky Derby:

While these all appear so trivial and random, you can cash out here by relating these bets with the initial bets. Some, like the prop bets related to horse racing e.g. name, starting position, jockey’s age etc. can be tied to the horse in the outright betting odds.

You can use prop bets as an additional bet on your initial one. If you’re betting on the favourite to win, you can make side bets on its jockey’s age, its starting position, and the starting letter of its name. 

Depending on the Triple Crown betting sites, you may even parlay props together. This can lead to monumental winnings even for a $10 bet or less. That is why signing up for multiple sportsbooks is deal. Find that one book that will let you parlay props.

Betting Strategies

Each of the Triple Crown races require a different betting strategy since each is a bit different. The Kentucky Derby, being traditionally the first race may have the most unexpected surprises. Things like “nerves” or horses being overestimated or underestimated are common, especially since there is limited data outside of the smaller horse races.

The Preakness Stakes, which is the second race and the shortest of the three, tend to have the least upsets. Oddsmakers can now rely on the Derby as a gauge of how the horses perform. Usually, Triple Crown threats win this race after they win the Kentucky Derby. If they falter, it’s at the Belmont Stakes, the home of upsets.

The Belmont Stakes, opposite of the Preakness Stakes is the longest racetrack and the most grueling. Factors like fatigue or “choking” can manifest here as plenty of Triple Crown contenders have faltered or couldn’t even make it to the track. 

As such, the Belmont Stakes tends to have a higher number of upsets. But despite this “frequency”, don’t expect this to be an “upset city” as favorites still tend to win out over time.

As far as betting markets, the Kentucky Derby has by far the most to offer. 

It can be similar to the NFL’s Superbowl as it has countless props usually not offered in other horse racing markets. But while the Preakness Stakes and Belmont Stakes don’t have the same amount of markets, their betting lines do not get steamed as much.

This is a good opportunity to bide your time and do more research or wait for better lines to be released. No such luxury with the Derby where you take what you can get or bank on those exotic props. 

How does the Triple Crown betting work?

Triple Crown betting tends to be available all year round, especially the Kentucky Derby. Odds usually open as early as during the current iteration of each race. Due to special circumstances, like the 2020 COVID-19 pandemic, betting odds may be taken off the board or changed more frequently. 

When Triple Crown odds are released ahead of time, these are usually known as “Futures” bets. A bet on these means you will have to wait until after the results are determined to cash. If you are patient, this works. But these odds can be taken off the board if news that significantly impact the bet is broken.

Betting this early has its advantages, however. You may be able to get a better value on some bets, especially if things change as the months go. Betting limits are lower here so there’s no harm in putting a little bit if you find a bet you like.

2020 Triple Crown Schedule

The Triple Crown traditionally takes place around the springtime in May. All three races are within five weeks of each other in this order: Kentucky Derby, Preakness Stakes, and Belmont Stakes. The Preakness Stakes is two weeks after the Derby and the Belmont Stakes is three weeks after the Preakness Stakes.

This 2020 marks the first time the races were in a different order and much further apart thanks to the COVID-19 pandemic. For the first time ever, the Belmont Stakes was the first leg of the Triple Crown and has been shortened to 1 ⅛ miles from its usual 1 ½ miles. 

The 2020 Triple Crown was scheduled: 

As in 2019, the NBC and all its streaming platforms aired the 2020 Triple Crown races beginning at 3 PM ET for each..

With this new format and the absence of an audience, there could have been some impact on the horse racing. 

Triple Crown Betting history

All three Triple Crown races have their share of history including betting. Most recently, all three have begun reporting record betting handles nearing $100 million. Thank the legalization of sports gambling in America and the consistent popularity of horse racing. Triple Crown betting sites have popped up very quickly. 

But of the three Triple Crown races, the Kentucky Derby is the most popular. It also offers the most betting markets and is the most scrutinized amongst both bookies and players. Both the Preakness Stakes and Belmont Stakes also receive significant betting action, however.

Here are some notable betting records within the Triple Crown:

Our take-aways

Each race in the Triple Crown has its own identity, bet accordingly

The three jewels of the Triple Crown are not all the same. The Kentucky Derby may be the most prestigious and offer the most in terms of betting markets, but the Belmont Stakes is the hardest. It is also the race with the biggest upsets. The Preakness Stakes is a bit more straightforward and a shorter race and is likely a chalk-heavy event.

Pick favourites or underdogs, but be committed 

Like our two fictional gamblers in our anecdote, you either choose to bet heavily to win money or be more laid back and treat betting like a hobby or a lottery. But you can’t flip between the two. Stay committed. If your strategy is to invest thousands to win hundreds, weigh the risks and see if it is feasible. Have a betting budget and know your limits.

The Triple Crown is only becoming more popular among bettors

All three races in the Triple Crown have reported record handles with two, the Kentucky Derby and Preakness Stakes having done so in the last few years. With sports betting becoming more available and more appealing, expect more betting money to keep coming.

About the Author

Trent Reinsmith
Trent Reinsmith

Trent’s your man when it comes to all things sports. He covers a wide range of sports for Sports Betting Sites, and has been published in some pretty reputable outlets, such as USA Today Sports, Vice, Bloody Elbow, Fight! Magazine, UFC 360, and Narratively. Trent’s got the inside track on all the happenings in the world of sports.

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