Forget the near-misses and the ones that got away. We’ve dug into the betting archives to uncover the stories of punters who actually broke the bookies at the Cheltenham Festival.
From stable lads with insider knowledge turning a tenner into a million to canny each-way bets that cleaned up at triple-figure odds, these are the accumulators that define what’s possible.
You’ll learn the specific strategies behind these monster bets, how timing and place terms made all the difference, and why these legendary wins still shape how savvy punters approach the multiples market today.
Conor Murphy’s 64,000/1 Masterpiece
Four months before the Festival, Murphy walked into his local Bet365 and placed £50 on a five-horse accumulator that would require absolute perfection.
The selections were as follows:
- Sprinter Sacre
- Simonsig
- Bobs Worth
- Finian’s Rainbow
- Riverside Theatre
All trained by his boss, all carrying the weight of his annual salary on their shoulders.
Here’s where it gets properly interesting. That £50 bet wasn’t a stab in the dark, it was insider knowledge wrapped in a betting slip. Murphy looked after Finian’s Rainbow personally and watched these horses work day in, day out. He knew what Henderson had in the yard before the official hype machine kicked into gear.
The bet paid £1 million (capped by Bet365’s maximum payout) though the true odds of 64,000/1 would have delivered over £3 million. Murphy, to his credit, turned up for work the next morning.
The £34,825 Seven-Timer That Broke Day One
Fast forward to 2024, and William Hill were counting its bruises after one particularly shrewd customer decided to go through the card on opening day. The punter staked a fiver and by close of play, they were staring at £34,825.94.
What makes this bet particularly interesting is the mix of banker material and smart value picks. Slade Steel got things rolling in the Supreme at 9/2 under Rachael Blackmore. Then came the Willie Mullins treble that bookies still have nightmares about Gaelic Warrior (5/2), State Man (4/11), and Lossiemouth (4/6) all obliging.
But here’s where the accumulator moved from decent win to monster payout:
- Chianti Classico took the Ultima at 11/2.
- Lark In The Mornin delivered in the Boodles at 6/1.
- Corbetts Cross, trained by Emmet Mullins, romped home by 17 lengths in the finale at 15/8.
William Hill’s Lee Phelps admitted it wasn’t an ideal start to the week, describing the customer as taking “bookie bashing to the extreme”.
The £40,000 Each-Way Masterclass:
In 2023, a William Hill customer demonstrated that each-way accumulators deserve far more respect than they typically receive.
The bet was modest: 50p each-way on a seven-fold accumulator covering day two of the Festival for a one-pound stake.
The selections were Bronn at 50/1, Lieutenant Rocco at 100/1, Captain Teague at 33/1. Only one of them actually won—Impaire Et Passe at 5/2 in the Baring Bingham.
Without William Hill’s extra places offer, Captain Conby (sixth at 15/2) and Lieutenant Rocco (fourth at 100/1) would have been dead weight. Instead, they contributed to a return of £40,929.31.
The £10,210 Near Miss That Still Won Big
Sometimes the most remarkable bets are the ones that nearly broke the bookies entirely. In 2025, a Ladbrokes customer placed 8p each-way on a Heinz bet for 57 combinations covering six horses, total stake £9.12.
While the masses piled into odds-on certainties, this punter went hunting:
- Lecky Watson at 18/1
- Jimmy Du Seuil at 14/1
- Latenightpass at 12/1
- Marine Nationale at 9/2
- Jazzy Matty at 13/2
- Bambino Fever at 5/1
Five of the six won. The five-fold alone paid 70,536/1.
But Latenightpass in the Cross Country Chase, leading at the last fence, only to be collared by Stumptown and beaten seven lengths into second. Had he held on, the punter would have collected £138,919.55.
Instead, they walked away with £10,210.19 from a £9.12 stake. A consolation prize that most of us would cheerfully accept, but one that will forever carry the sting of what might have been.
The Accidental Yankee: 2003’s Student Jackpot
In 2003, a student landed not one but two winning Yankee bets during his student days. The bets were placed weeks before on some of the biggest Cheltenham Festival races, securing prices that would vanish by race day.
Yankee one: Azertyuiop (Arkle, 7/4), Youlneverwalkalone (NH Chase, 14/1), One Knight (RSA Chase, 12/1), Best Mate (Gold Cup, 6/4). Return: £2,800+.
Yankee two: Azertyuiop, Rooster Booster (Champion Hurdle, 4/1), Youlneverwalkalone, One Knight. Return: £4,000+.
Cheltenham Festival Accumulator Comparison
Here’s a table to help you compare the top accumulator payouts for Cheltenham:
| Punter | Year | Stake | Return | Bet Type |
|---|---|---|---|---|
| Conor Murphy | 2012 | £50 | £1,000,000 | 5-fold Acca |
| Anonymous | 2024 | £5 | £34,825 | 7-fold Acca |
| Anonymous | 2023 | £1 | £40,929 | 7-fold e/w Acca |
| Anonymous | 2025 | £9.12 | £10,210 | Heinz (57 bets) |
| Student Punter | 2003 | £11 | £6,800+ | Two Yankees |
The Common Thread
Study these bets closely and patterns emerge. The biggest winners weren’t thrown together on the morning of a race; they were constructed weeks or months in advance when prices still offered value. Conor Murphy placed his bet in November and the 2003 Yankee was assembled weeks before. These punters weren’t reacting to the market, but they were ahead of it.
There’s also the insider knowledge angle. Murphy saw Henderson’s horses every morning. He knew which ones were thriving, which ones were carrying condition, and which ones would improve for the Festival hill with a top Cheltenham jockey onboard. That’s not cheating, that’s using your advantages.
Finally, the 2023 winner didn’t need winners… they needed places, and they found them at 100/1, 50/1, and 33/1. That’s not luck, but understanding how bookmaker concessions create value where none appears to exist.
Final Thoughts
The Festival is famously difficult for punters. Four days of relentless competition, 28 races, and enough variables to make your head spin. But these stories prove that multiples are legitimate vehicles for life-changing wins.
The key is realistic expectations. For every £1 million winner, there are thousands of losing slips feeding bookmakers’ bottom lines. The punters who landed these monsters didn’t bet beyond their means. Conor Murphy’s £50 was significant but not reckless, the Heinz bettor risked less than a tenner, and the each-way wizard staked a single pound.
The biggest Cheltenham accumulators ever landed weren’t the product of desperation or chasing losses. They were calculated, researched, and staked at levels that made the maths work in the punter’s favour.
Related: The Biggest Cheltenham Festival Races (By Prize Money And Prestige)
