Cheltenham Festival

The Biggest Betting Wins in Cheltenham History

2 hours ago

| BY Ben Chopping

Cheltenham betting history dates back to the very establishment of the Cheltenham Racecourse and its nascent days of minor flat racing in the early 19th Century.

Over the many, many years since, the course has seen several horses defy the Cheltenham odds and secure their faithful backers huge payouts.

Naturally, not all of the biggest payouts Cheltenham has ever seen were made public or celebrated in the press. Even so, we know of a some truly big winners and can assume many more based on the outsiders that have won.

Biggest Cheltenham Betting Winners

We’ll begin with the horses that have secured victories at some incredibly long odds to force some of Cheltenham’s biggest payouts. Chief among these is a famed 1990 runner who still sits atop the Cheltenham betting records.

Norton’s Coin ran in the 1990 Gold Cup at absurdly long odds of 100/1. Contributing to the eventual winner’s odds drift was grey favourite Desert Orchid at 10/11. Desert Orchid won in 1989, but Norton’s Coin ended three-parts of a length up on Toby Tobias. Desert Orchid secured third behind a fair bit behind the 100/1 long shot.

Much more recently – only last year, in fact – another horse made Cheltenham betting history by making good on their 100/1 horse racing odds. Running in the 2025 Triumph Hurdle, Poniros was way down the list from the 5/4 favourite East India Dock. In Poniros’ first public hurdling, the outsider won by a neck.

The other modern 100/1 marvel is Hipparchus. In the Grand Annual Handicap Chase of 1954, the five-year-old somehow overcame the competition and the bookies’ predictions to secure one of the biggest Cheltenham betting wins ever for its supporters.

Famous Cheltenham Punter Stories

Being a jump racing event with a relatively low win rate for favourites, punters have long secured big payouts for backing outsiders. Now, fans can even use the bet builder to stack those odds into bigger returns.

In 2012, one Connor Murphy backed five horses trained by his boss, Nicky Henderson, and was richly rewarded for doing so. He put down a £50 accumulator on a 12/1, two 6/1 shots, an 8/1, and a 10/1 horse, ending in the Ryanair Chase victory for Riverside Theatre. He pocketed the maximum £1 million, but it could have been £3 million!

That five-fold set Cheltenham betting records for its mighty return. Joining Murphy with another of the famous Cheltenham punter stories from 2012 is Phil Williams. The former footballer caught Son of Flicka at 66/1, which looked to be a punt. Then, the odds plummeted to 16/1, and the horse ended up winning him £900,000.

This year, there will be plenty more long odds picks battling to get their names, and the names of their backers, in the Cheltenham betting history books.