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Cheltenham Betting: The Ultimate Review

The world of horse racing is full of high-profile race festivals, taking place throughout the UK and many parts of the world. Very few hold the same level of nostalgia for racing fans as the Cheltenham Festival. Throughout this Cheltenham betting guide, we’ll take you through some of the key historical moments, introduce the best sportsbook covering the festival, and offer you some valuable insights that will help take your betting to new heights. Read on for the full report, or navigate to your area of interest through the menu below.

Page topics: click to go to your favourite topic!
Best bookmakers for Cheltenham

Discover their characteristics


How we choose the bookies

Under Over

Win, Each-Way, Show Bet


Topofthegame, A Plus Tard & Altior

Big Names

Tony McCoy, Barry Geraghty & more


Facts, stories and betting


Your questions answered

There is an abundance of information out there to help you on your quest of enlightenment. The Cheltenham Gold Cup being the pinnacle of the great event, we dive deep into all aspects. You can see below our list of recommended betting sites to start off with.

Betting on Cheltenham: The Best Operators

Choosing a sportsbook to bet with is more about trust than the objective quality of the product. Gambling is an industry that sits in a very unique spot and operates solely as an agreement between the product and the end user. If you’re looking to achieve great things betting on Cheltenham, then this list of strong contenders below is a great place to start.

The top 5 Cheltenham Sportsbooks
Bookmaker Bonus Offer Features Rating Secure Link T&C’s
Up to £20 14+ 93.62% 5/5 Visit Site! Full T&Cs Apply! 18+ New UK+IRE customers. Paypal and certain deposit types and bet types excluded. Min €5 bet within 14 days of account reg at min odds 1/2 = 4 x €5 free bets. Free bets valid for 4 days on sports, stake not returned, restrictions apply. T&Cs apply.
Up to £10 13+ 92.48% 4.5/5 Visit Site! Full T&Cs Apply! *New customers only. Min Deposit: £10. First deposit matched up to £10. 1 x wagering at odds of 1.75+ to unlock Free Bet. Debit Card & PayPal deposits only. This offer is valid for 7 days from your new account being registered.
Up to £30 11+ 91.23% 4.5/5 Visit Site! Full T&Cs Apply! Under the terms of this Promotion, eligible members will receive £30 in free bets at the Site. In order to receive the welcome offer, members must first place a qualifying bet. A qualifying bet is a ‘real money’ stake of at least £10 with odds of 1/2 (1.5) or greater. Bets that are ‘Cashed Out’ do not qualify. First qualifying bet must be placed within 30 days of registration. Please gamble responsibly. 18+
Up to £10 12+ 92.99% 4.5/5 Visit Site! Full T&Cs Apply! New players after 30.09.2020 | Valid on first Sports bet | Min. dep. £10 req. | Min. £10 wag. on first bet with min. total odds of 3/4 to qualify | Bet must be settled | Bonus Wag. req.1x on min. 2-fold combi bets (min. 1/4 odds each selection) with min. final odds of 4/5 | Virtual bets and cashed out bets do not qualify | One-time offer | Bonuses credited following working day | 18+ | begambleaware.org
Up to £20 11+ 91.89% 4/5 Visit Site! Full T&Cs Apply! 18+. UK+IRE only. Min first bet £5 at odds 1/2 or more. Tote and Pool excluded. Must be placed within 14 days of account reg. £20 credited as 4 x £5 free bets. Not valid with CashOut. Free bet valid for 4 days. Free bet stake not returned.

How we Chose the Best Bookmakers for Cheltenham

Picking the operators to conduct your business with is no easy task. The following sections we will explain the process we use to navigate through the vast amount of options and produce results of top bookies based on an objective assessment.

You can probably tell that we take this task extremely seriously, applying stringent sampling techniques to produce accurate results for out reporting mechanisms. The following sections will brush over each area of performance that we take a keen interest when accessing the quality of Cheltenham betting sites.

The Importance of Payouts

There is nothing more important for a new punter to a sportsbook than the initial payout rates of the betting markets. The first instance we have taken to ensure you get the best value is by calcualting the returns on a series of different races at Cheltenham. The table below you can see what we predict your return on investment to look like. You can minus these values from 100 to calcuate the commission being taken by the bookmaker.

Best Cheltenham Betting Offers

When it comes to identifying the best Cheltenham betting offers, it’s always wise to keep your finger on the pulse. That means being active on popular social media channels, and regularly checking out sites like ours and the bookmaker platforms themselves. Bookies will often roll out extravagant marketing campaigns that are targeted over social media, in an attempt to gain viral traction and more exposure to people interested in certain upcoming sporting events.

Live Betting and Streaming

You can watch horse racing through the sportsbook live streaming functionality that many platforms are offering. But the true nature of the technology is one that extends far beyond the basic needs of the modern-day punter. Within these platforms there are extensive markets available for selection once events have begun, even in a sport such as horse racing, punters are able to leverage the power of in-play betting to their advantage.

Number of Markets Available

There are of course many markets available to be bet upon before the race begins. You can usually define these markets into two separate categories. The exotic bets involve a certain degree of difficulty, and usually return odds much longer than their straight bets counterparts. With the advent of daily lotteries, jackpot prizes and multiples, you can really enhance your ability to score big at the horse racing sportsbook.

The Type of Cheltenham Markets

When it comes to betting at the Cheltenham Festival, there are several different strategies you can adopt to maximize your chances of scoring a win. First and foremost, pay attention to the daily race card. You can use this to effectively plan your bets throughout the day, and not jump into a bet sheerly based on instinct and emotion. The types of markets vary from picking a winner, to predicting the horses to finish in the top 3 or making a safe and secure bet on a favorite covered by an each-way bet. Below we’ll touch on the two main types in more detail.

Straight Bets

With straight bets the punter has the option to bet on very simple and easy to analyse market types. These are typically a horse to win the race outright, or a horse to finish in the top X amount of places. Usually, a horse with long odds in a densely packed field will be backed with odds of around 12/1, an effective way to guarantee yourself a win is to study the form of such horses intensely, then select it to win but cover yourself with an each-way bet also, returning ¼ of the winning odds should your horse finish at the top end of the field, in the each-way places.

Huge welcome offer Wide selection of markets Easy to interact on mobile
Bonus up to £10
Full T&Cs Apply! *New customers only. Min Deposit: £10. First deposit matched up to £10. 1 x wagering at odds of 1.75+ to unlock Free Bet. Debit Card & PayPal deposits only. This offer is valid for 7 days from your new account being registered.

The Win Bet

The win bet is exactly what it says on the tin. By no means an easy market to play on, it relies on a deep knowledge of the horses running and an understanding of the conditions and how this effects the field. But perhaps the most crucial aspect is luck, this is horse racing after all!

The Place Bet

Place bets are made when the horse in question has a particularly strong showing in previous races, but calling it to win would be a bit over optimistic. You can back a horse to finish in the top places as a single bet, or choose a horse to win and cover it with an each-way bet to the same value as we have already mentioned.

The Each-Way Bet

The each-way bet is one of the most popular bets people make at a sportsbook, let alone horse racing. It is so popular that it has redefined horse racing. Punters love this bet because horse racing is obviously a very difficult thing to predict. Horses can be judged against one another and it is not impossible to say generally who the best picks within a field are, but winning the race usually requires a certain degree of luck that cannot be anticipated. The each-way bet allows you to have the excitement of picking a winner, and yet be covered when the luck doesn’t go your way.

Exotic bets on Cheltenham

Those of you interested in exotic Cheltenham betting won’t be too dissatisfied by the generous selection of markets at the five operators we have chosen above. There are a number of ways you can get involved with the exotic bets on the sportsbook. Go in with an open mind, and listen to your heart. As winning one of the bets below is almost never attributed to any kind of scientific process.

The Tricast Bet

Three horses running There is the Tricast bet which requires you to select three horses who will finish first, second and third. This is a lot harder than it sounds, and successfully calling this type of bet will earn you a huge win. This has become one of the favourite bets of punters who stand on the terraces, and the rewards are handsome. Of course, the chances are extremely low and you only hear the stories of big winners very rarely. So we wouldn’t say you should expect to be a winner, and it’s more of a challenge.

The Forecast Bet

Two horses running The Forecast bet is a reduced style Tricast bet, you’ll just need to predict the horse that finishes in first place and second place. Predicting these two horses is not the easiest of tasks, but you’ll need to do your due diligence. Of course, it is an easier version of the aforementioned type, thus, you stand a greater chance of winning. Even so, it is still difficult and we’d recommend studying how the horses have been running and the surface they favour, before making your final decision.

Superfecta bet

Four horses running Perhaps the ultimate exotic bet you can make at Cheltenham betting sites is the superfecta. This massive odds bet will take you through to the jackpot level win categories. But in order to land such a massive bet you have to call the exact lineup of the finishing horses from 1st to 4th place. Making this bet is a massive gamble and trying to scientifically predict these outcomes is not advised.

All you Need to Know about the Cheltenham

Cheltenham info
Cheltenham Racecourse
Nome: Cheltenham
Headquarters: Cheltenham, Gloucestershire
Year of foundation: 1815
Sponsor: Ryanair
Website: Cheltenham
Race Type: Flat
Surface: Turf
Prize Money: £625,000

The Cheltenham Festival is a classic race event that is testament to the culture of British horse racing. There are many things that make this event unique, and punters around the world focus their horse racing fandom on the crown jewel of the race meet, the Cheltenham Golf Cup. It is certainly rival to the Grand National in terms of fanfare and has become a massive event for not only Horse Racing fans, but the general public too.

The first race of Cheltenham took place back in 1815. This was a time when horse racing truly was the sport of kings: attendees at the first Cheltenham races would have been from the upper echelons of society. Take a look below at a classic example of the races at Cheltenham, and how they have evolved into an internationally recognized event.

Nowadays, the crowd is famed for its roar, and the stands are jam-packed for the races that are held over four days. Enormous amounts of money are bet, and last year nearly 70,000 people attended the opening event. An incredible amount, and just demonstrates the success of this wonderful race, and the prestige it holds with the fans is second to none.

A unique aspect of Cheltenham is that although it is a famous festival, it generally only feature horses from the British Isles, as it doesn’t attract foreign runners. Of course, there have been some in the past, however, in recent times this has not been the case. With the festival continuing to grow, it could change in the near future.

A YouTube Channel of Cheltenham

All the Info on the Horses of Cheltenham

To be in a strong position to make accurate calls on the events of the races taking place throughout the day, you need to have a background understanding of the runners, the trainers and the teams of individuals that surround the day. To get off and running on this journey of gambling enlightenment you have to consider a multitude of variables. The key information points of this race over the last 5 years are outlined for you in the sections below.

The Past 5 Placed Winners

Let’s take a quick look at the winners over the past 5 years of the Gold Cup, you can clearly see from the outset that all horses in this field represent the strongest participants throughout the history of this event. In the future, we will look back at horses such as Al Boum and Anibale Fly as horses that were at the top of their game.

Cheltenham Gold Cup Last 5 Year Results
Year 1st (Horse, Trainer) 2nd (Horse, Trainer) 3rd (Horse, Trainer)
2019 Al Boum, P Townend Anibale Fly, B J Geraghty Bristol De Mai, D A Jacob
2018 Native River, Colin Tizzard Might Bite, Nicky Henderson Anibale Fly, A J Martin
2017 Sizing John, M Harrington Minella Rocco, J O’Neill Native River, Colin Tizzard
2016 Don Cossack, B J Cooper Djakadam, R Walsh Don Poli, D N Russell
2015 Coneygree, N De Boinville Djakadam, R Walsh Road To Riches, B Cooper

Who are the Best Trainers?

The best trainers in horse racing are highly sort after individuals that can command a very high fee to be responsible for a training camp of several high-potential horses. This art form goes back centuries, and those that possess the instinct and knowledge to train horses to compete in the biggest races of the yearly calendar. Looking above you’ll notice R Walsh the man responsible for training Frankie Detorri’s horse Djakadam.

The Best Horses of Cheltenham

Many fantastic breeds race across the Cheltenham grass, but none have enjoyed quite as much success as the three horses you see in the sections below. These three horses have shown tenacity and exemplified strength, perseverance and guile to outperform all the competition at the Cheltenham Gold Cup.

  • Arkle (horse)

    The legend of the Cheltenham Gold cup is undoubtedly Arkle, the quick mare won three times consecutively in the 1960’s.

  • Best Mate (horse)
    Best Mate

    Best Mate is probably the most prevalent name of the present era, the horse has been huge in the Cheltenham cup recently.

  • Kauto Star (horse)
    Kauto Star

    Kauto Star has made a strong case for legendary status at the Cheltenham Gold Cup, winning twice in 2007 and 2009.

Legends of the Past

Now let us look at some of the legends of the race. Although it is hard to talk about horses here, as only three-year-olds are allowed to compete, meaning there is a new field every year, there have still been some memorable names throughout the years. What’s more there have been some world-class jockey’s and trainer’s that have graced the race over the years.

Horses Producing the Most Winners

There have been some fantastic races over the years, and utilising the power of Cheltenham bookmakers has never been more important than it is now. There below you can see the most decorated horses of the Cheltenham Festival. But don’t bother keeping your eyes peeled for these runners, they are long retired from the sport.

The Best Horses Over the Years at Cheltenham
Horse Races Run Number of Winners Owner Years Active
Arkle 35 27 Anne Grosvenor 1964 – 1966
Best Mate 30 14 Jim Lewis 2002 – 2004
Flyingbolt 22 9 Jean Wilkinson 1964 – 1966
Sprinter Sacre 13 7 Caroline Mould 2013 – 2016
Penelope 6 4 Augustus FitzRoy 1803 – 1808

Cheltenham Records

If you’re looking for a deeper insight at the Cheltenham Festival, and expand your knowledge of this event, then the three sections below are a great place to begin your journey. You can quickly realise the stars of Cheltenham, whether you just need some fresh ammunition for horse racing chats down the pub, or you’re looking to impress at the bookies down at Cheltenham Racecourse, it’s a good idea to have the three individuals below in the back of your mind.

  • Golden Miller
    Horse with the Most Wins in the Gold Cup

    Golden Miller can only be considered a legend of the Cheltenham Gold Cup, notching up 5 wins in his career during the 1930’s.

  • Pat Taaffe
    The Leading Jockey

    There have been no other great jockeys to outperform the prestigious achievements of Pat Taaffe. The young Irishman won 4 races during the 1960’s.

  • Dorothy Paget
    The Leading Owner

    Dorothy Paget is the leading owner throughout the history of the Cheltenham Gold Cup, winning 7 titles with 3 different horses.

History of Cheltenham and Betting

Cheltenham Festival is an event that is steeped in tradition, and the races have been going for several centuries. If you’re looking to gain a valuable insight into the key milestones of Cheltenham betting, take a quick look at the timeline down below to make some mental notes.

The history of the Cheltenham infographic

Discover the Best Bookies for the Cheltenham

Cheltenham and Bookmakers Sponsorship

Whether you’re a newly formed horse racing event, or an age-old race like the Grand National, there will certainly be interest from sponsors to promote the event. At the Cheltenham Festival there are two brands that stick out. The main sponsor of the festival is Magners, the alchoholic beverage. As for Cheltenham betting sites, Betway horse racing is the main sportsbook to cover this event and features regular special offers for their users in and around the day of the event.

Which Bookies Should You Avoid?

Bookies to avoid include unlicensed and unregulated operators. Those that do not protect you when things go wrong and leave you out to dry. For more information on the best bookies for betting on sports in the UK, visit our homepage.

Facts and Anecdotes about Betting on Cheltenham

There are always occasions when massive bets land and the punters go wild. But the two stories you can see below really take the bacon in this regard. With a massive lottery style competition making one punter exceedingly rich, and a massive outsider taking the race victory in the 70’s.

  • Fractional odds
    High Priced Winners!

    There have been some exceptional winners throughout the years at the Cheltenham Gold Cup. Most notably is the prestigious efforts of the 70/1 outsider in the 1970’s.

  • Lots of money
    Punter wins £182K

    One lucky punter won over £182K from a £2 bet on the Cheltenham Gold Cup during the 2019 festival. Entering a lottery style bet to predict 6 winners.

Paul Nicholls

He is an experienced horse that has matured, and he has done the talking himself in the last few runs. We are really excited about running him in the Cheltenham Gold Cup.

Paul Nicholls


Now that we have concluded our Cheltenham review, this is your opportunity to reach out and clarify anything that still confuses you. If you still have some burning questions, please read our FAQ below or feel free to send us an email. at info@bestbettingsites.com.

Does every site cater to betting on Cheltenham?

Every site we have featured on this page offers extensive betting market coverage for the entire Cheltenham Festival.

Can I watch the Cheltenham live?

You can watch the Cheltenham Festival live across several different domains, on desktop and even on mobile at high quality sportsbooks.