The Triple Crown is thoroughbred racing’s three-race championship for three-year-olds: the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes.
It is a five-week series in which the story can change quickly. The Derby usually brings the biggest field and the most chaos. The Preakness often reshapes the picture entirely. The Belmont can either become a national event built around a possible sweep or a very different handicapping puzzle with fresh horses and new pace dynamics.
Read on for our full Triple Crown betting guide, where we discuss each race’s unique handicapping dynamics, how the story changes after each leg, and where you can bet online legally.
Where to Bet on the Triple Crown Online
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2027 Triple Crown Schedule
| Race | Date | Track | Distance | Purse |
| Kentucky Derby | May 1st, 2027 | Churchill Downs | 1 1/4 miles | $5 million |
| Preakness Stakes | TBA | Pimlico Race Course | 1 3/16 miles | $2 million |
| Belmont Stakes | June 5th, 2027 | Belmont Park | 1 1/2 miles | $2 million |
Where the 2027 Triple Crown stands
It remains to be seen whether there will be a Triple Crown bid in 2027.
We’ll get our first look with the Kentucky Derby on May 1st, and we’ll find out for sure once the Derby winner’s team announces whether they’ll aim for the Preakness Stakes.
What’s Different About the 2027 Triple Crown
The 2027 Triple Crown should feel more familiar after three unusual seasons.
One major difference is that the Belmont Stakes returns to Belmont Park after running at Saratoga from 2024-2026 due to a reconstruction project at its usual host track.
During the Saratoga stint, the Belmont Stakes ran at 1 ¼ miles rather than its traditional 1 ½ mile distance. Back at Belmont Park, the race should again look more like the “Test of the Champion.”
Legal Triple Crown Betting Sites
The easiest and safest way to bet on the Triple Crown online is to use a licensed advance deposit wagering (ADW) website or app. Licensed ADWs operate in most states and provide direct access to each track’s official pari-mutuel wagering pools.
Takeout rates are set by the host track, not the ADW, so the same exacta on any Triple Crown race pays the same regardless of which ADW you use.
Where ADWs differ is in rebate programs, deposit promotions, account minimums, and whether they cover all three Triple Crown races (not all online racebooks have access to the Kentucky Derby).
With that in mind, two ADWs in particular stand out for offering an optimal combination of handicapping features, promotions, and access to every Triple Crown race:
States with Legal Online Triple Crown Betting
Online Triple Crown betting is legal in most states through licensed advance deposit wagering platforms. Even some of the states that prohibit online sports betting allow pari-mutuel wagering:
Horse Racing
How Triple Crown Betting Works
Triple Crown wagering happens almost entirely through pari-mutuel pools. In a pari-mutuel system, all bets of a given type go into a shared pool, the track takes a percentage (the takeout, typically 15% to 25% depending on the bet type), and the remainder is split among winning tickets.
The Triple Crown betting odds shift up to each race’s post time based on how the public bets, and your final payout is determined by the closing pool, not the odds you saw when you placed the wager.
The standard Triple Crown wager menu at any licensed horse racing betting site includes standard straight bets (e.g., win or show), exotics (e.g., exacta or trifecta), and multi-race bets (e.g., the Derby Day Pick 6) with massive payout potential.
See our horse racing betting guide for detailed explainers and straightforward examples showing how each bet type works.
Churchill Downs also runs the Kentucky Derby Future Wager, a series of pari-mutuel pools that open months before the race and let bettors lock in early odds on horses pointing toward the Derby.
How the Triple Crown Betting Dynamics Change in Each Race
The Triple Crown’s three races test different handicapping skills and reward different betting strategies. A bettor who succeeds at the Derby with a wide-coverage exotics approach can lose money applying the same approach to the Preakness, where the handicapping dynamics are fundamentally different.
Kentucky Derby
The Derby is the chaos race. It draws the biggest field, the most casual money, and the widest mix of opinions. That combination tends to create both noise and opportunity.
Up to 20 horses load into the gate, one of the largest fields in American racing, and the sheer number of combinations explodes the exotic pools: 380 possible exactas, 6,840 possible trifectas, 116,280 possible superfectas.
Longshots hit at a fairly high rate here because the field is too large for the public to handicap precisely. Spread-and-cover exotic strategy dominates serious Derby play, and the pari-mutuel pools are large enough to support it without crushing the prices.
See our full Kentucky Derby betting guide for a discussion of this year’s contenders, handicapping considerations, the latest odds, and more:
Preakness Stakes
The Preakness Stakes tends to be a more compact and form-dependent race, but that does not necessarily make it easier.
Instead, the questions change. Which Derby horses are coming back on short rest? Which runners skipped Louisville and arrive fresher? How much should bettors trust what they just saw two weeks earlier?
Fields are usually smaller (often 8 to 12 horses), the turnaround from the Derby is only two weeks, and favorites and second choices have hit at a much higher rate over the last quarter-century than they do in the Derby or Belmont.
The recurring betting angle is “new shooters,” horses that skipped the Derby entirely and enter the Preakness fresh while the Derby field carries fatigue. New shooters frequently run in the money at attractive prices.
Tighter win bets and exactas with new shooters underneath tend to bet better than spread-everything strategies that work at the Derby.
For a detailed discussion of this year’s Preakness Stakes betting dynamics, see our full guide:
Belmont Stakes
The Belmont Stakes is the puzzle race. By the third leg, the field has been reshaped by which horses came out of the Derby and Preakness sound, which trainers chose to skip races, and which fresh shooters entered to take advantage of the tired horses that ran both prior legs.
When a Triple Crown is on the line, the live contender gets bet to near even-money regardless of his true win probability, which opens value across the rest of the field. When no sweep is at stake, the Belmont reverts to a different kind of handicapping problem driven by pace, distance, and rest.
For this year’s analysis and current odds, see our Belmont Stakes betting guide:
How the Triple Crown Picture Develops
The first leg sets the table. The second leg decides whether the story grows larger or falls apart. The third leg either crowns a rare champion or closes the book on another season that stopped short of history.
A part of what makes betting on the Triple Crown so compelling is that the handicapping picture changes after each race in predictable ways. Knowing what to look for at each stage helps you decide where to deploy your bankroll across the five-week stretch.
Before the Kentucky Derby: The early window is dominated by Derby futures speculation through the KDFW pools and prep race results from January through April.
The winners of the Florida Derby, Blue Grass, Santa Anita Derby, Wood Memorial, and Arkansas Derby typically anchor the betting picture by mid-April.
After the Derby: The whole outlook pivots on the Derby result each year. If the Derby winner is sound and pointed at the Preakness, a Triple Crown bid is alive, and the storylines for the next four weeks write themselves.
If the Derby winner skips the Preakness Stakes (an increasingly common choice), the bid ends before the second leg, and the Preakness becomes a separate handicapping problem with new shooters in play.
After the Preakness Stakes: Either a horse arrives at the Belmont with a chance to become the 14th Triple Crown winner, or the Belmont becomes a final-leg pace puzzle with no series stakes attached.
The two scenarios bet very differently. A live Triple Crown contender will be hammered down to near even-money in the Belmont win pool, which makes value plays elsewhere on the ticket more attractive.
List of All Triple Crown Winners
Only 13 horses have won the Triple Crown in the 107 years since Sir Barton became the first in 1919. The 37-year drought between Affirmed (1978) and American Pharoah (2015) was the longest gap in series history.
| Year | Horse | Jockey | Trainer |
| 2018 | Justify | Mike Smith | Bob Baffert |
| 2015 | American Pharoah | Victor Espinoza | Bob Baffert |
| 1978 | Affirmed | Steve Cauthen | Lazaro Barrera |
| 1977 | Seattle Slew | Jean Cruguet | William H. Turner |
| 1973 | Secretariat | Ron Turcotte | Lucien Laurin |
| 1948 | Citation | Eddie Arcaro | Ben A. Jones |
| 1946 | Assault | Warren Mehrtens | Max Hirsch |
| 1943 | Count Fleet | John Longden | Don Cameron |
| 1941 | Whirlaway | Eddie Arcaro | Ben A. Jones |
| 1937 | War Admiral | Charles Kurtsinger | George Conway |
| 1935 | Omaha | Willie Saunders | James Fitzsimmons |
| 1930 | Gallant Fox | Earl Sande | James Fitzsimmons |
| 1919 | Sir Barton | Johnny Loftus | H.G. Bedwell |
Why Triple Crown Sweeps Are So Rare
The odds against a Triple Crown sweep are brutal before you even factor in the five-week timeline. A single horse has to win three high-profile races at three different distances against three different fields, with only two weeks between the Derby and the Preakness and three more between the Preakness and the Belmont.
Among the legitimate Triple Crown contenders since 1978, only American Pharoah and Justify have completed the sweep. Nearly two dozen others have won the Derby and Preakness but lost the Belmont.
What’s changed more recently is that some Derby winners no longer attempt the sweep at all. Modern training schedules, owner incentives tied to stud value, and richer alternative summer races (the Travers in particular) have pushed connections toward strategic skips.
The last two Triple Crowns illustrate the trend. Sovereignty’s connections chose to skip the 2025 Preakness Stakes after winning the Kentucky Derby, with trainer Bill Mott openly prioritizing the horse’s long-term campaign over the historical attempt. Sovereignty then returned to win the Belmont Stakes by three lengths.
Similarly, Golden Tempo’s team opted to skip the 2026 Preakness Stakes after winning the Kentucky Derby. Golden Tempo returned fresh for the Belmont Stakes and won it. That’s two straight Kentucky Derby winners who have traded a Triple Crown bid for a rested Belmont run, and both decisions paid off on the track.
The industry has responded on two fronts. The first is money. Churchill Downs raised the Derby purse from $3 million to $5 million in 2024, and 1/ST Racing simultaneously raised the Preakness purse from $1.5 million to $2 million and created a separate $5 million bonus for any horse that wins the Preakness, the California Crown Stakes, and the Pegasus World Cup.
The second is ownership. In April 2026, Churchill Downs Incorporated agreed to acquire the Preakness Stakes intellectual property from 1/ST Racing for $85 million, consolidating two of the three Triple Crown races under a single owner.
Proposals to spread the Triple Crown calendar out have circulated for years but never gathered serious support. The CDI acquisition changes the incentives: a single entity now controls two of the Triple Crown’s three race brands and has an obvious reason to protect the series’ commercial value by discouraging Derby winners from skipping the Preakness.
Whether the acquisition results in a move to a three-week Derby-to-Preakness gap in 2027 (the most-discussed proposal) remains to be seen.
Triple Crown Betting FAQ
Wes Burns has more than a decade’s worth of experience as a writer, researcher and analyst in the legal gambling industry and is co-founder of BettingUSA.com. As a former professional online poker player, Wes approaches his work from the viewpoint of players.