How to Bet on The Kentucky Derby

Since 2005, the field size of the Kentucky Derby has either been 19 or 20 runners in 14 of the last 16 years. In 2020 when the race was postponed to October due to the pandemic, the field size was just 15. In 2015 a total of 18 came out of the starting gate.

A large and relatively inexperienced group of runners going a new distance in front of over 100,000 fans is not only a challenge to the horses, but also to the bettors looking to make a score.

Road to the Kentucky Derby

The Kentucky Derby is restricted to three-year-olds, so a horse has just one shot of getting adorned with Roses in their career and in some years, it is not easy to make the cut.

In September of each year the Road the Kentucky Derby points race starts. Over the following seven months there are over 30 races awarding qualifying points to the top four finishers.

Early on the points are distributed on a scale of 10-4-2-1 to the top four finishers but by the time we reach the final major preps that include races like the Florida Derby and Santa Anita Derby, the points have increased to 100-40-20-10 to the top four.

The top 18 in the points standings are guaranteed a starting spot in the gate on the first Saturday of May, along with one starter each from the European and Japan Road to the Kentucky Derby series.

Types of Kentucky Derby Bets

If you are wondering how to bet on the Kentucky Derby, it is good know there are nearly countless ways to wager on the race, regardless of your bankroll and your risk tolerance.

For those of you looking for a low risk wager, a simple win or place wager might be in order. If you are looking to make a big score, betting on the Kentucky Derby offers that as well.

Here are the main wagers offered when betting the Kentucky Derby:

Win

If you wager $2 to Win on your horse, you collect only if your horse finished first.  A $2 win wager on the 2021 winner Medina Spirit returned $26.20.

Place

If you wager $2 to Place, your horse must finish first or second for you to collect. But remember, you don’t get the Win payoff, just the Place payoff, which is generally smaller than the win payoff. Medina Spirit paid $12.00 to place in 2021.

Show

If you wager $2 to Show, your horse must finish first, second, or third. But remember, you only collect the Show payoff, because three different horses get paid off. Medina Spirit returned $7.60 to show while 25-1 longshot Mandaloun paid $13.40, and third place finisher Hot Rod Charlie paid $5.20.

Exacta

The Exacta involves selecting the top two to finishers in the race in exact order. A common way to play an Exacta would be a $2 Exacta box. If you liked the #1 and #2 horse, a $2 Exacta box would cost $4. If those two horses ran first and second in either order, you win. In 2021 the Medina Spirit-Mandaloun exacta paid $503.60. Over the last 22 years the average exacta has returned $935. The high was $3,010 in 2019 and the low was $31 in 2016.

Trifecta

Hitting a Trifecta gets a bit harder as it involves correctly selecting to top three finishers in exact order, no easy task in a 20-horse field. The average $1 payoff for a trifecta dating back two decades is $6,686. While boxing three horses in the trifecta for $1 is just $6, it gets pricier as you add more horses. A $1 trifecta box using five horses costs $60.

It is generally better to key one or two horses (the contenders you have the strongest opinions on) in the top spot and spread in the second and third spots. For example here are a few ways to get good coverage with modest investments on a $1 increment:

1,2 with 1,2,3 with 1,2,3,4,5,6 = $16

1,2 with 1,2,3,4 with 1,2,3,4,5,6 = $24

1,2,3 with 1,2,3,4 with 1,2,3,4,5,6 = $36

There is good news for bettors with smaller bankrolls. Most tracks including Churchill Downs lowered the increment on trifectas from $1 to .50 in the past few years, meaning you can spread more and cover more horses you think have a shot of landing in the money.

Superfecta

The Superfecta gets even harder as you must correctly select the top four finishers in the race. Most tracks have lowered the Superfecta bet increment to .10 cents, including the 2020 Kentucky Derby. However, Churchill Downs raised it back up to $1 for the 2021 running.

The Superfecta can lead to a huge score in the Kentucky Derby as the $1 return over the last 22 years has averaged $64,615 with a high of $432,127 in 2005 when longshot Giacomo pulled off the big upset. We have seen a few small Superfectas in recent years with favorites winning. Nyquist topped a $542 payoff in 2016 and with American Pharoah on top paying $634 in 2015, but overall expect to see a big payoff if you are able to solve this puzzle. 

Other Exotic Wagers

There are countless other wagers on Kentucky Derby Day including horizontal wagers like the Pick 3, Pick 4, Pick 5, and Pick 6 wagers that include the Kentucky Derby and other races on the card. There are daily doubles, wagers involving races combining Oaks Day and Derby Day and even a Super High Five which involves selecting the top five finishers of the Derby. The $1 payoff in the 2021 Super High Five was $296,769.

Kentucky Derby Future Wager

Did you know you can wager on the Kentucky Derby winner months in advance? Churchill Downs hosts five separate Kentucky Derby Future Pools, starting in November where horseplayers can get an early bet in on who they think will be the Derby winner.

The pools are limited to 23 separate betting interests and a 24th is “All Others” which consists of every other Triple Crown nominated horse. “All Others” was the betting favorite in the first three pools in 2021.

By the time Pool 4 came around in March bettors had a pretty good idea of the top contenders and “All Others” drifted up to 7-1 while Life Is Good was bet down to 2-1. Medina Spirit, the eventual winner was 39-1 in Pool 4.

The last Kentucky Derby Future Wager Pool closed on March 28, with five major Derby preps still to be run. Essential Quality was the favorite at 4-1 while Medina Spirit closed at 13-1.

Value can be occasionally found in the Kentucky Derby Future Wager, but you have to remember there are no refunds if your selection does not make it to Louisville on the first Saturday of May. Just weeks after Life Is Good was bet down to the favorite in Pool 4 the colt suffered an injury that knocked him off the Kentucky Derby trail, leaving his backers with worthless tickets.

How to Bet the Kentucky Derby Online

If you are not heading out to the track to bet on the Kentucky Derby the best way to wager on the race is online.

It is a good idea to sign up with an online racebook in advance of the Kentucky Derby and there are plenty of incentives waiting for you.

New players can get a generous sign-up bonus, player rewards, free past performances and more at the top rated legal racebooks in the U.S.

Here are several of the top rated racebooks:

Twinspires

The official wagering platform of the Kentucky Derby, Twinspires is one of the most popular racebooks in the U.S. In addition to a generous sign-up bonus, Twinspires offers free past performances and live streaming of the races on their platform. Twinspires offers a VIP Elite program with great players rewards and flexibility to wager from any of your portable devices.

TVG

TVG is offering a $300 Risk Free wager for new players and has a wide array of players rewards including money back specials and wagering insurance. Their betting platform is one of the best in the business and their television network is available on Direct TV and Dish Network and can be streamed for free using the Roku or Firestick app.

AmWager 

AmWager boasts of an advanced wagering platform that is up to 60 times faster than its competitors. There is free streaming of the races online and up to a $500 sign up bonus. There are no minimum play requirements to earn cash rewards and they are deposited directly into your account daily.

Who to Bet On For Kentucky Derby

So now you have been introduced to the history of the Run for the Roses, how the horses get there, how to set up an online account and wager on the race, and the different bets available for the Kentucky Derby.

Now all you have to do is pick the winner, right? Here are a few things to ponder for your online Kentucky Derby betting.

Kentucky Derby Favorites

In a large and competitive field you would think the betting favorite would be up against it, but the Kentucky Derby betting favorite actually won six straight years from 2013 to 2018. In the last 22 years the betting favorite has seen the inside of the winner’s circle 10 times. However, from 1980 to 1999 the favorite came up short 20 years in a row.

Since Churchill Downs went from graded stakes earnings to a points system, the races have been run truer to form. In addition, the betting public may be getting more astute as well with more access to replays, speed figures and statistics.

Despite the favorite wining six years in a row, the average exacta payoff during that span came in at $305.33.

Long Shots in the Kentucky Derby

Despite favorites having a good run over the last two decades, don’t discount the occasional bomb, it is going to happen from time to time.

In 2004 Giacomo pulled off the big upset and returned $102.60 and just four years later Mine That Bird came flying up the rail to pull off an upset and return his backers $103.20. In 2019 Maximum Security was disqualified for interference and Country House was elevated to the winner, paying a hefty $132.40.  

Key Kentucky Derby Prep Races

The vast majority of Kentucky Derby winners are in action putting in their final prep race usually 21 to 35 days before the first Saturday of May.

The Florida Derby at Gulfstream Park has been the most productive prep race, with 24 exiting the race to go on and wear Roses. And they usually win their final prep. The last seven Kentucky Derby winners that came out of the Florida Derby won that final prep race.

In fact, if we include Maximum Security (who crossed the wire first but was disqualified), the last 11 Kentucky Derby winners won their final prep race.

The Toyota Blue Grass at Keeneland has produced the second most Kentucky Derby winners at 23 but has not been much of a factor over the last three decades. We have to go back to Strike the Gold in 1991 to find the last Derby winner to prep in the Blue Grass.

Other key final preps are the Wood Memorial at Aqueduct which has produced 20 Derby winners and the Santa Anita Derby which has produced 20 including the 2021 winner Medina Spirit.

Last 10 Kentucky Derby Winners

Key Kentucky Derby Trainers

Look no further than trainer Bob Baffert who has won the Kentucky Derby a record seven times although Medina Spirit could end up getting disqualified. Baffert has started 34 horses in the race and along with his seven winners he has run second three times and third three times.

Todd Pletcher has started more horses in the Kentucky Derby than any other trainer in history with 59 starters. Newly inducted to the Hall of Fame, Pletcher has won the Kentucky Derby just twice, with Always Dreaming in 2017 and Super Saver in 2010.

D. Wayne Lukas, who is still training at the age of 85, has saddled four Kentucky Derby winners, the last being Charismatic in 1999.

The only other active trainers with more than one win are Nick Zito and Doug O’Neill with two each.

Steve Asmussen, a two-time Eclipse Award winner for outstanding trainer has the most Kentucky Derby starters without a victory, currently 0 for 23.

Top Kentucky Derby Jockeys

Hall of Fame rider John Velazquez has won the last two editions of the Kentucky Derby aboard the Baffert trained Authentic in 2020 and Medina Spirit in 2021. He won his first Kentucky Derby aboard the Graham Motion trained Animal Kingdom in 2011 and booted home Always Dreaming in 2017 for Pletcher.

Kent Desormeaux is coming toward the end of his Hall of Fame career and has three wins, his most recent with Big Brown in 2008. Mike Smith won aboard Giacomo and Justify, the latter going on to win the Triple Crown.

Victor Espinoza won in back to back years in 2014 aboard California Chrome and American Pharoah in 2015. Mario Gutierrez rode both of Doug O’Neill’s winners, I’ll Have Another in 2012 and Nyquist in 2016.

Javier Castellano is the most overdue jockey still looking for his first Kentucky Derby ride. Four times the Eclipse Award winner for outstanding jockey, he is 0 for 15 in the Run for the Roses.

Irad Ortiz Jr. has won the Eclipse Award each of the last three years but is 0 for 5 in the Derby. His brother Jose, the Eclipse Award winner in 2017 is 0 for 6. They both seem highly likely to eventually win the race.

Post Positions in the Kentucky Derby

We hear a lot about the “dreaded one post” before the Kentucky Derby post position draw each year and breaking from the inside can be a disadvantage. No Kentucky Derby winner has come out of the one stall since Ferdinand in 1986.

The best posts are the 5 which has produced 10 Derby winners and the 10 post which has produced nine winners.

Posts 17 and outward were at a disadvantage in previous years, with just four winners from 126 starters. However, several of those wins were recent. Big Brown broke out of the 20 post in 2008, I’ll Have Another out of the 19 in 2012 and Country House out of the 18 post in 2019.

Last year saw Churchill Downs purchase a new starting gate that holds 20 horses. Previously they had an auxiliary gate for the outside posts and there was a small gap between the two gates and the outside gate was at a slight angle.

Moving forward if you like a horse that has an outside draw, I would not hold that against them. The “dreaded one post?”  Unless the horse had early speed, it will not do your pick any favors to break from the rail.  

Kentucky Derby Winning Running Styles

Going 1 ¼ miles on the first Saturday of May is a stamina test and it was difficult to take the field gate to wire. Perhaps not so much anymore.

When graded stakes were used to create the field, there were usually one or two sprint types that managed to get into the field, assuring a fast early pace that tended to favor horses that were stalking or closing.

In recent years the early pace has been more moderate, and we have seen on the lead types fare quite well.

War Emblem wired the field in 2002, the first to do so since the filly Winning Colors in 1998.

However, things changed in 2019 as Maximum Security set the early fractions and held on to win by 1 ¾ lengths. But after a 22-minute stewards’ inquiry, he was disqualified for causing interference at the top of the stretch.

In 2020 the Kentucky Derby was postponed because of the pandemic and run in October. Authentic was able lead from start to finish, returning $18.80 for the win. And last year Medina Spirit broke alertly, was sent to the lead and battled on gamely in the stretch to win by a half-length, paying $26.20.

So what does the future hold when it comes to running style? You should lean toward horses that like to be up front or in a stalking position where they could get to the lead by the top of the stretch. It is tough for deep closers to work their way through a large field.

The Kentucky Derby Winning Profile

Over the past couple of decades we have seen Kentucky Derby winners prep less and have more space between their races, but we still have a reasonable idea of what a winning profile for the Kentucky Derby winner looks like.

Ideally the horse has at last one start as a juvenile. Justify was the first Kentucky Derby winner to not have a start as a two-year-old since Apollo in 1882.

Heading into the Kentucky Derby they should have at least three starts under their belt, preferably four or five. Their last prep should be between 21 and 35 days prior to the Kentucky Derby.

It should be in a graded stake, and they should have a sharp final prep race. Don’t forget the last 11 to cross the wire first in the Kentucky Derby won their final prep. The last to lose was Super Saver in 2010 and he lost by just a neck in the Arkansas Derby.

There is nothing better when playing the ponies than making a score in the Kentucky Derby, which indeed will make it your two most exciting minutes in sports.

Photo Credit

ANDY LYONS / GETTY IMAGES NORTH AMERICA / Getty Images via AFP