You think Cheltenham Festival tipsters can’t lose? Better think twice! Numbers tell a different story – just 32% of outright favourites at Cheltenham crossed the finish line first between 2015 and 2025. My personal journey of betting against short-priced contenders spans 20 years, with ups and downs along the way.
The Cheltenham Festival stands without doubt as the National Hunt season’s crown jewel. The festival’s unpredictable nature makes it fascinating. The most reliable horses can stumble at crucial moments, and shocking upsets happen often. The numbers paint a clear picture – 28 out of 58 odds-on favourites failed to deliver since 2004.
Smart bettors can still spot useful patterns. Seven-year-old horses with past festival wins show an impressive 28% success rate since 2013. On top of that, the Coral Cup’s last ten winners mostly wore numbers from one through eight.
Sports betting tipsters become valuable allies for Cheltenham Festival betting because they help decode these complex statistics. These experts share their Cheltenham Festival predictions by 7 pm before race day. This timing lets you place bets with confidence.
This piece will walk you through the 15 best Cheltenham Festival tipsters. You’ll learn about their past performance, methods, and betting approaches that help make smarter choices during the festival.
Paul Kealy
Paul Kealy’s background
Bookmakers get nervous checking their liability sheets at the mention of Paul Kealy. The Racing Post’s senior tipster has built his reputation through decades of sharp analysis. He spots value opportunities that others miss. His career started during Racing Post’s early days. He worked his way up from a copy-taker to sports tipster before leading as the paper’s betting editor from 2001 to 2019.
Kealy’s track record speaks for itself. He won the Racing Post naps competition twice and stands among British racing’s most respected tipsters. His transparent approach sets him apart from others in the field. He takes time to explain each selection’s reasoning. This makes him both a tipster and a mentor for bettors who want to sharpen their analysis skills.
Paul Kealy Cheltenham Festival strategy
Kealy takes a systematic yet bold approach to the Cheltenham Festival. His Weekend Card column helps serious punters prepare for the festival and has become essential reading. Instead of just backing favourites, he searches for hidden gems offering real value.
He knows different races need different betting approaches. His handicap selections come from deep form study. Championship races need pace analysis and track condition assessment. His ante-post picks often feature carefully chosen longshots that usually shorten substantially by race day.
The festival sees Kealy heavily involved with exactas and trifectas, particularly in competitive handicaps and graded races. He says: “I don’t tend to do them anywhere other than Cheltenham and Royal Ascot, but you know the pools are going to be strong and they will more often than not beat the CSF and tricast”.
Paul Kealy notable wins
Kealy’s Cheltenham Festival record shows several picks that left bookmakers reeling. His recent standout performances include:
- A brilliant 2023 Festival where he picked Envoi Allen at 20/1 for the Ryanair Chase, Seddon at 20/1, plus placed horses Letsbeclearaboutit (16/1) and Conflated (22/1)
- The 2024 Festival, where he bounced back from early setbacks with winners like Protektorat, Shakemup ‘Arry, and Limerick Lace
- His 2022 selections featured Protektorat (20/1 each-way Gold Cup), Vauban (8/1 Triumph), and several other double-digit priced winners
These wins stand out not just for their odds but for Kealy’s logic. He spots crucial factors that markets miss, helping readers find similar opportunities on their own.
Paul Kealy success rate
Kealy doesn’t claim perfection, but his long-term results make him one of the most dependable Cheltenham Festival tipsters. His reputation grows thanks to honest reporting and steady results. Like all tipsters, he faces ups and downs – struggling early in recent festivals before making strong comebacks later in the week.
His success rate stands out for its longevity. Many tipsters shine briefly before their results become average. Kealy managed to keep his edge through racing’s development. Markets move on his opinions – bookmakers often reduce odds when he tips a horse, expecting increased betting activity.
Paul Kealy betting style
Kealy combines classic handicapping with smart positioning. He places single bets overnight or earlier to get the best odds. He knows timing matters as much as selection.
His method focuses on finding “the best-handicapped horses in races“. He studies form, maps race pace, and understands market psychology. The Cheltenham Festival brings out a unique pattern in his approach:
“I bet for fun as much as I bet to win,” he says, “and if there are enough competitive races with decent-sized fields I’ll have a crack. With all the extra places on offer these days, they’re well worth looking into”.
Kealy excels at breaking down complex races into clear, useful insights without losing analytical depth. His followers learn not just what to bet but why – creating smarter punters rather than blind followers. His systematic approach guides anyone looking for expert advice during the Cheltenham Festival’s excitement.
Tom Segal (Pricewise)
Tom Segal background
Racing fans know Tom Segal as “Pricewise” – he ranks among the UK’s most respected horse racing tipsters. His Racing Post career started in 1996, and he took charge of the prestigious Pricewise column in 2001. Segal sees race analysis as an intellectual puzzle rather than just a way to make money. This unique viewpoint has built his reputation over two decades.
Racing pages grabbed more of Segal’s attention than management textbooks during his studies at Cardiff University. He started his career at Raceform, where he sharpened his analytical skills by diving deep into race data. These early data skills became the foundation of his success at Racing Post. His knack for finding value bets has earned both respect and fear from UK bookmakers.
Tom Segal Cheltenham Festival strategy
Segal takes a unique value-focused approach to the Cheltenham Festival. He looks beyond obvious favourites and searches hard for horses with odds that exceed their winning chances. This explains why his picks often come with big prices that make bookmakers nervous.
His Cheltenham picks target races where betting markets might miss crucial factors. Recent festivals saw him back winners like Sir Gerhard in the Supreme Novices’ Hurdle, L’Homme Presse in the Brown Advisory, Flooring Porter in the Stayers’ Hurdle, and Protektorat in the Gold Cup.
Course form and improvement potential at specific distances catch his eye. He spotted this with L’Homme Presse, noting: “Should improve again for the step up to 3m½f and course form gives him the edge over Bravemansgame”. This eye for detail helps him spot value others miss.
Tom Segal notable wins
Segal’s career features many memorable Cheltenham Festival wins that have made him legendary among punters. His talent for spotting overlooked horses has brought big paydays to his followers:
- Royal Ascot saw him land three consecutive winners at odds of 33-1, 14-1 and 9-2. He proudly said: “Bang, bang, bang – they went in just like that”
- His 2023 Cheltenham Festival nap picked Feet of a Dancer in the Pertemps Final at 16/1, up from 12/1. He stated confidently: “everything stacks up for her”
- He spotted The New Lion at 9/4 in 2023, calling it “from a different cloth” and a “potential Champion Hurdle horse”
His market influence shows clearly – prices typically drop soon after he publishes his tips. This serves as proof of his impact on racing.
Tom Segal success rate
Segal’s achievements stand out because he focuses on longer-priced selections. He excels with horses priced above 3/6 and does particularly well in races with odds beyond 11/16 to 1. His legendary 10-week winning streak in 2005 helped punters win millions from bookmakers.
His method brings natural ups and downs. A strike rate around 1 in 8 from 61 races means he can face losing runs of 20 or more bets. Yet his value-based strategy pays off over time – one study revealed a 44% ROI based on £1 level stakes at suggested prices.
Results matter more in the long run than hit rates alone. Segal puts it simply: “Luck always plays a part… but when you’re tipping horses the day before a race, all your calculations go out the window if it pisses down”.
Tom Segal betting style
Segal keeps his own bets modest at £50 to £100 per race, though his tips have cost bookmakers millions. He finds intellectual satisfaction more rewarding than pure profit: “I bet for fun as much as I bet to win… it’s like a puzzle. I like the challenge of trying to work it out”.
His special talent lies in spotting “moments of clarity” – when race conditions, form, and circumstances come together perfectly. He explained one winning pick: “The race had fallen apart for him; everything had come right and I was able to see that”.
Professional integrity matters more to him than quick profits: “It’s a bit fraudulent if you’re a tipster and you don’t bet. If you’re having a bad run, you have to be willing to share it with the people who follow your tips”. This honest approach has earned lasting respect from punters and professionals in a field where reputations often fade quickly.
David Jennings
David Jennings background
David Jennings serves as the Racing Post’s deputy Ireland editor and brings Irish racing expertise to Cheltenham Festival punters. He joined the publication in 2012 and has become a leading voice in racing journalism. His coverage spans from breaking news to race analysis. His deep knowledge makes him an outstanding tipster, especially for Irish-trained horses at the Festival.
He hosts “Upping The Ante,” the Racing Post’s popular ante-post Cheltenham Festival show. The show has built a dedicated following among serious punters. Jennings examines the Cheltenham betting markets months before the event, which gives his followers time to find value.
Many tipsters focus only on British racing. Jennings’ Irish point of view offers fresh insights into yards like Willie Mullins and Gordon Elliott. Their influence at Cheltenham has grown into a big deal over recent years.
David Jennings Cheltenham Festival strategy
Jennings takes a portfolio approach to Cheltenham Festival betting. He builds a team of horses in a variety of races. His recent broadcasts show how he added Sir Gino to his Cheltenham Festival portfolio for the Champion Hurdle.
He spots class horses that others might undervalue early on. His words about Sir Gino show how he values raw ability: “I think he’s the most talented horse in training and on his day is unbeatable”.
He spots potential class angles in competitive handicaps. Speaking about one pick, he said: “There’s just something that suggests to me that he could make the jump to the next level, and he’s probably the only one in this race who can”. This focus on class sets his method apart from pure form analysts.
David Jennings notable wins
Desertmore House at 10/1 for the Cross Country Chase stands among Jennings’ best recent Cheltenham picks. This tip showed his skill in finding and improving horses with specific Festival targets. He explained: “He travelled, he jumped, he attacked every obstacle that came his way, and the interesting thing is that after the race Martin Brassil said ‘yeah, Cheltenham is the number one aim'”.
He builds his portfolio throughout the season. His reputation comes from finding horses whose prices drop as the Festival gets closer. His early ante-post picks often offer better value compared to their starting prices.
Beyond Desertmore House, his portfolio includes several notable Festival picks, with horses priced as high as 25/1 and 50/1.
David Jennings success rate
His success comes from his deep connection to Irish racing, which gives him valuable insights about horse preparation. His role as deputy Ireland editor lets him watch training developments closely. He often spots improving horses before they show their true ability on the track.
The growing popularity of his Upping The Ante series lets viewers track his selections openly. Regular discussions about winning picks on the show suggest he maintains a solid success rate.
His credibility stems from explaining his reasoning behind each selection. Rather than just giving tips, he helps followers understand why he makes each pick.
David Jennings betting style
Jennings looks at class angles and trainer intentions when making selections. His Desertmore House tip shows how he values insider knowledge: “Martin Brassil said, ‘yeah, Cheltenham is the number one aim'”.
He favours horses that can improve, especially those trying longer distances or new challenges. About Desertmore House, he noted: “He’s an up-and-coming horse who’s only run twice over the banks. He was second to Busselton in the La Touche, only caught late”.
His mix of deep racing knowledge and understanding of Cheltenham’s unique courses creates a detailed approach. This makes him valuable to punters looking for an edge at jump racing’s most competitive festival.
Johnny Dineen
Johnny Dineen background
Johnny Dineen stands out from other Cheltenham Festival tipsters because he knows racing from many angles. Most analysts study the sport from a distance, but Dineen worked as an on-course bookmaker in Ireland before becoming a professional punter. This hands-on experience helps him understand both sides of betting.
David Jennings and Dineen now co-host “Upping The Ante,” Racing Post’s popular ante-post Cheltenham Festival show. His no-nonsense style and practical knowledge have earned him many fans who appreciate his unfiltered opinions.
Dineen writes a weekly column for Racing Post’s Members’ Club Ultimate subscribers. He shares his betting picks and views based on years of experience. His racing career started as a weekend clerk for bookmakers, and he built his name as a sharp operator in betting circles.
Johnny Dineen Cheltenham Festival strategy
Dineen takes a unique approach to the Cheltenham Festival. He puts more emphasis on the first two days. “One thing I’ve learned in 18 years is that the best two days for punters are Tuesday/Wednesday. If you’re in dire straits Thursday morning, the chances of you coming out of the week in front are slim. Thursday/Friday is a bookies bonanza”.
His strategy comes from attending Cheltenham since 2004, first as a bookmaker then as a punter. He bets big on shorter-priced horses that he thinks offer value, whatever the odds. Dineen’s motto rings true: “Money on is better than money gone”.
He doesn’t worry about prices when he feels confident about a horse. “If I think something will win, it doesn’t bother me how short he is”. This self-assurance leads him to make bold claims about horses he believes can’t win.
Johnny Dineen notable wins
Dineen’s recent Cheltenham Festival picks show his talent for spotting winners. He picked several successful horses, including Chianti Classico, Montys Star (without the favorite), Shanbally Kid, and a remarkable 33/1 shot with Stellar Story.
His two “Dineen Diamonds” – El Fabiolo and Energumene – proved to be winning selections. He also spotted winners in Corach Rambler, Impaire et Passe, and Delta Work. These picks showed his skill across different types of races.
Dineen makes bold ante-post recommendations. He told punters to back Flame Bearer for the Sporting Life Arkle with confidence: “There is plenty of 16-1 available for the Arkle and that could look a very big price come Sunday night”.
Johnny Dineen success rate
Dineen’s results tell an interesting story. Though he makes his living as a professional punter, his festival performance shows how tough high-stakes betting can be. After doing well on Tuesday and Wednesday during one festival, his picks went “0 from 15 in bold type Thursday/Friday“.
These mixed results show the challenges that even professional bettors face at top events. He admits that “not being as sure of winning as he was” comes with being a professional punter.
He stays honest about his wins and losses. After one tough stretch, he described it as “a damage limitation exercise” where he “did turn a nasty losing week into just a moderate deficit.” He calls this skill “an art that can help you stay in business over a long period”.
Johnny Dineen betting style
Dineen bets big – he “bets in bundles of money which need to have elastic bands on”. He places substantial wagers, sometimes making “£30,000/16,000 singles” on horses he really likes.
His approach differs from typical tipsters. While others chase longshots, Dineen “mostly bets favorites”. He sees value in shorter odds where others might not. He speaks his mind about popular horses, once saying about a well-backed runner: “He might have won for the last two years but I give him absolutely no chance this time”.
Dineen combines sharp form study with good information sources. He believes that “networking with other sharp people gives him an edge”. His success comes from using multiple information streams rather than relying on just one approach.
Robbie Wilders
Robbie Wilders background
Robbie Wilders represents a fresh wave of Cheltenham Festival tipsters with his analytical mindset. He started at Racing Post in 2018 and joined their tipping team in early 2022. His expertise in ante-post betting helped him rise faster through the ranks, and he excels at spotting value bets early.
These days, people know him best as the writer of “Ante-Postman,” a free weekly email column that spots betting value before others. His recommendations have such weight that they influence market movements, which shows how much serious punters trust his picks.
Robbie Wilders Cheltenham Festival strategy
Wilders takes a systematic approach to Cheltenham Festival. He looks beyond mainstream analysis and spreads his selections across multiple horses. Rather than focusing on favorites, he builds a diverse portfolio of picks.
His strategy paid off brilliantly during a recent festival’s final day. He picked winners in all seven races – picks that could have made a massive 112,515/1 accumulator if combined!
Robbie Wilders notable wins
His recent success stories include tipping Baratablet at 3/1 (which won at 11/4) at Newcastle. This shows his skill at finding consistent winners.
He showed his value-spotting talents at Cheltenham with Our Boy Stan, recommending it as an “each-way bet at double-figure odds“. He noted trainer Ben Pauling’s comments, saying: “You have to take remarks like that on board when they come from a trainer of Pauling’s caliber”.
Robbie Wilders success rate
His detailed study of form, track conditions, and race factors has earned him quick recognition. The racing community values his thorough approach.
Bettors appreciate his tips because they provide reliable, well-researched guidance. His selections prove their worth by beating the starting price (SP) regularly.
Robbie Wilders betting style
Wilders stands out with his clear betting philosophy: “Don’t include short-priced favorites in extensive multiples – odds-on chances are always beaten”. This principle shapes how he approaches Cheltenham Festival betting.
He blends deep data analysis with real-time race factors. Horse racing fans describe him as “a novel thinker and sound judge of horse racing outcomes”.
His weekly ante-post tips through Racing Post emails give Cheltenham Festival punters valuable insights before market shifts reduce potential returns.
James Hill
James Hill background
James Hill has worked at the Racing Post through many Cheltenham Festivals. His racing expertise spans nearly two decades at the tipster table. He joined the publication in 2005 and became a respected voice in the racing community. Today, he provides a full range of racing tips that include ante-post selections, premium tips, free tips, and play-of-the-day recommendations.
Hill’s career stands out for his racing previews that help bettors understand major racing events better. He’s a key member of the Racing Post’s expert team and appears in video content with other tipsters to analyze various race meetings.
James Hill Cheltenham Festival strategy
Hill’s Cheltenham Festival approach focuses on finding overlooked contenders who have specific advantages on the course. To cite an instance, he made a bold call about the Cross Country Chase by naming Stumptown his “banker of the meeting.” Hill pointed to the horse’s impressive Cheltenham record as key evidence.
His strategic insights often go against popular beliefs. He once noted that while it’s “rare for a five-year-old to win the Champion Hurdle,” some young horses might be “worth chancing”. This shows his readiness to back horses that break typical Festival patterns.
Hill stays focused on what matters most. He doesn’t get caught up in stories about “plot horses” or “well-handicapped old sweats”. Quality comes first in his analysis, as shown when he called Stumptown simply “the best contender in the race”. His detailed approach looks at factors like age (noting Stumptown was “still only eight”) and course advantages (seeing how cross-country courses can balance out directional preferences).
His recommendations come from his deep analysis of how horses adapt to Cheltenham’s unique challenges. Yet his advice stays clear and simple. Punters appreciate his direct verdicts like “Back him” that cut through the complexity.
Comparison Table
| Tipster | Current Role | Notable Festival Wins/Picks | Betting Style | Success Rate/Track Record |
|---|---|---|---|---|
| Paul Kealy | Racing Post Senior Tipster & Former Betting Editor (2001-2019) | Envoi Allen (20/1), Seddon (20/1), Protektorat, Shakemup ‘Arry, Limerick Lace (2024) | Makes bets at an overnight stage, specialises in handicapped horses, uses exactas/trifectas at major festivals | Two-time Racing Post naps competition winner |
| Tom Segal (Pricewise) | Racing Post Pricewise Columnist (since 2001) | Feet of a Dancer (16/1), The New Lion (9/4), Multiple Royal Ascot winners (33/1, 14/1, 9/2) | Stakes £50-£100 per race, targets value bets | About 1 in 8 strike rate, 44% ROI on £1 level stakes |
| David Jennings | Racing Post Deputy Ireland Editor | Desertmore House (10/1), Multiple ante-post selections at 25/1 and 50/1 | Specialises in ante-post betting, avoids short-priced favourites in multiples | Not specifically mentioned |
| Johnny Dineen | Co-host of “Upping The Ante” | El Fabiolo, Energumene, Corach Rambler, Impaire et Passe | Specialises in class angles and trainer intentions, uses a portfolio approach | Mixed results, strong early week performance |
| Robbie Wilders | Racing Post Tipping Team Member | Baratablet (3/1), Our Boy Stan (double-figure odds) | Stakes large amounts, prefers favourites, targets Tuesday/Wednesday races | Consistently beats starting prices |
| James Hill | Racing Post Racing Expert | Stumptown (Cross Country Chase banker) | Specializes in ante-post betting, avoids short-priced favourites in multiples | Not mentioned |
Key Takeaways
These insights will help you navigate the complex world of Cheltenham Festival betting by understanding what separates successful tipsters from the rest.
• Timing is crucial for value – Top tipsters like Paul Kealy place bets at overnight stage to secure best odds before markets move • Focus on Tuesday/Wednesday races – Expert Johnny Dineen emphasizes these are the best days for punters, with Thursday/Friday favoring bookmakers • Value beats favorites consistently – Tom Segal’s 44% ROI proves that hunting overlooked contenders at longer odds outperforms backing obvious choices • Irish expertise provides an edge – David Jennings’ insider knowledge of Irish trainers like Willie Mullins offers unique insights into Festival preparation • Ante-post betting maximizes returns – Robbie Wilders’ early selections consistently beat starting prices by identifying value before markets catch up
The most successful Cheltenham Festival tipsters combine deep analytical skills with strategic timing, focusing on value rather than popularity. Their transparent approach to both wins and losses, coupled with decades of experience, makes them invaluable guides through racing’s most unpredictable week.
FAQs
Q1. Who are considered the top Cheltenham Festival tipsters? While there are many respected tipsters, some of the most prominent include Paul Kealy, Tom Segal (Pricewise), David Jennings, Johnny Dineen, and Robbie Wilders. Each brings unique expertise and strategies to their Festival predictions.
Q2. What betting strategies do successful Cheltenham tipsters use? Top tipsters often focus on finding value rather than just backing favourites. They may place bets early to secure better odds, analyse Irish-trained horses closely, and pay special attention to Tuesday and Wednesday race,s which are considered better for punters.
Q3. How reliable are Cheltenham Festival tipsters’ predictions? Success rates vary, but the best tipsters consistently beat starting prices and provide long-term profitability. For example, Tom Segal (Pricewise) has shown a 44% ROI on £1 level stakes over time, though individual festivals can be unpredictable.
Q4. Is it better to follow one tipster or multiple for Cheltenham? Following multiple respected tipsters can provide a more balanced approach, as each has different strengths. Some excel at ante-post betting, others at specific race types or trainer insights. Combining perspectives may help create a more robust betting strategy.
Q5. How important is timing when following Cheltenham Festival tips? Timing is crucial. Many top tipsters, like Paul Kealy, place bets at the overnight stage to secure the best odds before markets move. Following ante-post tips from experts like Robbie Wilders can also help maximize potential returns by identifying value early.