Cheltenham Top 5’s: Big Cheltenham Odds Winners & Upsets

Updated: June 1, 2026 at 11:57 am GMT+1

The Cheltenham Festival is a glorious time for punters. There is simply so much to bet on from a multitude of Cheltenham free bets – and we are not just talking about the win and each-way prospects of all the runners in the 28 Cheltenham races which make up this annual betting feast.

The outcome of the Prestbury Cup, the award handed to the country which provides the greatest number of winners, has become a really popular Cheltenham betting market and last year, that went to the Irish, who were responsible for 18 of the 28 winners.

Amongst them were some real shocks, such as Premier Magic, who won the Festival Hunters’ Chase at odds of 66/1. But, in truth, very few Cheltenham Festivals go by without a ‘skinner’ – that being a winner who ‘skins’ the punters and benefits the bookmakers.

Nowadays, you can actually place bets on the price of the biggest winner during the course of the four-day festival, and, as you can see below, huge odds winners are more common than you may think.


Latest Cheltenham Festival Betting Offers

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William Hill Sports logo
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William Hill Sports
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Midnite
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KWIFF
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Betfred
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Bet442 Sport
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Betfair
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Grosvenor
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talkSPORT BET
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Betway
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Highbet Betting
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Available to verified customers residing in the UK. Opt-in is required. Place your first bet of £10 at minimum odds of 1/1 on any sports market within 7 days of registering. Get £30 in Free Bets (1x £10 Horse Racing Free Bet + 1x £10 Football Acca Free Bet + 1x £10 Basketball Acca Free Bet) T&Cs apply. 18+ Please gamble responsibly.
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Jeffbet
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Tote
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bet365
Bet £10, Get £30 in Free Bets for the World Cup
Min deposit requirement. Free Bets are paid as Bet Credits and are available for use upon settlement of qualifying bets. Min odds, bet and payment method exclusions apply. Returns exclude Bet Credits stake. Time limits and T&Cs apply. Registration Required

Norton’s Coin (100/1) - 1990 Cheltenham Gold Cup

Trained by Sirrell Griffiths, a dairy farmer from Carmarthenshire in West Wales who trained three horses for a ‘hobby’. Norton’s Coin’s victory in the Cheltenham Gold Cup was the biggest upset in the race.

It was probably the biggest upset in the history of the Festival. There was no fluke about his big race win, he won the race on merit, but given he won just once in 18 subsequent starts (including an outing at Royal Ascot under Lester Piggott) form students cannot fathom how it happened to this day.


Labaik (25/1) - 2017 Supreme Novices’ Hurdle

OK, 25/1 is not an enormous priced winner by Festival standards but don’t let an SP get in the way of a good story!

It wasn’t a case of when the Irish-trained lined-up for the 2017 Supreme Novices’ Hurdle, it was a case of ‘if’. Coming into the race, his form figures over jumps read Ref-Ref-1-1-Ref.

Those refusals were all a case of him refusing to start/race, and prior to this, his final run on the flat saw him leave the starting stalls 30 lengths behind the others. But, to the surprise of many, he took a liking to the famous Festival roar and consented to race.

Two miles and three minutes and 53 seconds later, he quickened clear to beat 13 rivals comprehensively. Six weeks later, Labik planted himself at the start in the Champion Novice Hurdle at the Punchestown Festival and raced just once more in his chequered career.


Carrickboy (50/1) - 2013 Byrne Group Plate

Sadly, no longer with us, jockey Liam Treadwell will always be remembered for winning the Grand National on 100/1 shot Mon Mome in 2009, but his greatest ride may well have been in 2013 when winning the Festival’s Byrne Group Plate (now called the Festival Plate) aboard Carrickboy at odds of 50/1.

Rarely do you see a horse make all in a Festival race, and an all-the-way winner in a 22-runner handicap is as rare as a snowflake in the summertime.

But bravely kicking on from the front clear two furlongs from home, Carrickboy delivered another shock winner on a day which was one of the best ever for the bookmakers.

Collectively the winners on Thursday March 14th 2013 were priced as follows - 20/1, 25/1, 7/2, 17/2, 50/1, 16/1 and 14/1. Just three favourites were placed on the day. It was a punter’s graveyard.


Cue Card (40/1) - 2010 Champion Bumper

Cue Card spread-eagled the field when trouncing his rivals in the 2013 Ryanair Chase, but circumstances, including a pelvic injury which kept him off the track for almost all of the 2014 season, meant he never ran at the Festival again until 2016.

And just how well was he travelling in the 2016 Gold Cup when coming-a-cropper three from home?

Ultimately, Cue Card retired with nine Grade 1 wins on his CV. But where did it all begin? In the 2010 Champion Bumper where the British-bred horse sprung a 40/1 shock by trouncing highly-regarded opposition by eight lengths at odds of 40/1. The race card report from the following day’s Racing Post read: “romped home!”


Minella Indo (50/1) - 2019 Albert Bartlett Novices’ Hurdle

He may be most well-known for this victory in the 2021 Cheltenham Gold Cup, and his near miss in the gruelling 2020 RSA Novice Chase will live long in the memory, but his undoubtedly large engine was not apparent in the early part of his career.

Prior to arriving at the 2019 Festival to compete in the Albert Bartlett Novices’ Hurdle, he had been beaten on all three of his previous starts. But he won “in command” by two lengths according to the formbook, and the rest, as they say, is history.


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Scott McGlynn
Scott McGlynn

Scott McGlynn draws on over 30 years of sports betting and casino experience, bringing data-led insights and first-hand knowledge to our readers. An authoritative and trusted voice in the gambling industry, Scott ensures our readers are always informed on the very latest sports and casino offerings.

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