Nicky Henderson’s Cheltenham winners

Nicky Henderson has a legendary record at Cheltenham Festival. Learn more about his winners and where he ranks among the most successful trainers.

Nicky Henderson is one of the most successful trainers in the sport, with there being few races in The National Hunt calendar that he has not won. The Cheltenham Festival, however, is where Henderson has been especially successful – helping take an impressive number of horses to victory.

But just how many Cheltenham winners has he had? Below is our breakdown of his history within the Festival, delving into his winners, most famous wins, and more.

How many winners has Nicky Henderson had at Cheltenham Festival?

As of the 2025 edition of Cheltenham, Nicky Henderson has produced 75 winners dating back to 1985. These winners have been across multiple different races, including notable events such as the Cheltenham Gold Cup and the Champion Hurdle.

Gold Cup

Not only the main feature event of Cheltenham, but among the biggest prizes in the sport, training two horses to win the Cheltenham Gold Cup certainly ranks as one of the more impressive achievements by Nicky Henderson. However, despite competing for many years, it was not until 2011 that he first won this prestigious title with Long Run – which he followed up soon after in 2013 with Bobs Worth.

Champion Hurdle

Consisting of nine winners produced by Henderson, the Champion Hurdle is his most successful event at Cheltenham. Some of his most impressive winners include See You Then, who won three in a row in 1985, 1986 and 1987, and Buveur d’Air who won it back-to-back in 2017 and 2018.

Arkle Challenge Trophy

The Arkle Chase has been kind to Nicky Henderson, earning him a total of eight winners over the years – making this his second-most successful race at Cheltenham. Most recently, Henderson worked with Jango Baie and won the 2025 version, further proving the longevity he has in the sport.

Nicky Henderson’s Cheltenham winners since 2020

Below see the list of Cheltenham winners that Nicky Henderson has had since 2020. 

Some of Nicky Henderson’s most famous Cheltenham wins

Having trained 75 Cheltenham winners as of 2025, Henderson has had plenty of success and notable wins throughout his training career. Here is our list breaking down a few of the highlights.

See You Then – Champions Hurdle (1985)

As previously mentioned, Nicky Henderson’s victories date back to the eighties, getting his first in 1985 with See You Then. Despite not being the favourite at 16/1, See You Then became a huge part of Henderson’s dominance of the mid-eighties, taking home three Champion Hurdles wins in a row. This victory in 1985 was especially impressive due to the horse pushing through well-documented tendon issues.

Bobs Worth – Gold Cup (2013)

Although not necessarily considered to be one of the more talented horses that Henderson trained, he was an extremely hard-working one. So much so that he pulled through from fifth position late in the race to achieve an impressive and memorable Gold Cup victory in 2013.

Shishkin – Arkle Challenge Trophy (2021)

One of his most dominant wins came in the form of Shishkin’s triumph at the Arkle Challenge Trophy in 2021. Winning by 12-lengths, jockey Nico De Boinville led him to a landslide victory in which no other horse came close.

Constitution Hill – Champion Hurdle (2023)

For multiple reasons, Constitution Hill’s Champion Hurdle triumph in 2023 makes it into this list. Not only did he win by 9-lengths, but he also notched Nicky Henderson’s wins in this race to a record nine. Constitution Hill is a huge name within National Hunt racing, and this race is just one demonstration of why he’s earned this reputation.

Where does Nicky Henderson rank among Cheltenham’s most successful trainers?

There have been many extraordinarily successful trainers that have produced some of the best horses known in the sport. And Nicky Henderson, with all the success he has enjoyed, has certainly put himself in the conversation among the best.

You may be thinking though, where exactly does he rank among Cheltenham’s most successful trainers?

If you are looking at purely number of wins, of course, Willie Mullins takes the biscuit with a record 113 Cheltenham winners. He equalled his own record of having ten winners in one year in 2025 after originally completing the feat in 2022.

Nicky Henderson, meanwhile, finds himself in second for number of wins at Cheltenham with his 75 (though, he did at one point have the highest number of wins, until 2018). This does however place him as the best British trainer in the Festival’s history!

Despite being the second-best trainer, here, as a whole, when it comes to the Gold Cup, Henderson does fall slightly shorter. Winning it twice is impressive, but unfortunately for the legendary trainer others have won it more. Tom Dreaper holds the current record having won it five times and Basil Briscoe comes in second place with four, tying with Willie Mullins, Paul Nicholls, Vincent O’Brien, and Fulke Walwyn.

Then Owen Anthony and Henrietta Knight have won it three times, placing Nicky Henderson a few positions off the top spot.

Will we see any Nicky Henderson Cheltenham winners in 2026?

With the National Hunt season underway, we can now start to look ahead and see if there’ll be any familiar names that crop up throughout Cheltenham Festival. But will we be seeing any more winners from Nicky Henderson?

Despite not yet being confirmed, we can expect to see some of Henderson’s horses featuring in 2026. Below are some of the more likely horses to star:

Jonbon

Although yet to win at Cheltenham Festival, Jonbon will almost certainly feature at the 2026 edition. After failing to win here for the past three years running, Jonbon will be wanting to set the record straight. Jonbon is expected to compete in the Champion Chase.

Jango Baie

A possible contender for the Cheltenham Gold Cup in 2026, Jango Baie is one to keep an eye on. Winning the Arkle Novices’ Chase in 2025 suggests he is a horse that, although still improving, will be well prepared for the challenges ahead.

Constitution Hill

Facing recent falls and setbacks has caused doubt for some as to whether Constitution Hill could feature. Henderson, however, appears to believe that he can still compete in the 2026 Champion Hurdle, meaning there is still a chance he makes an appearance.

Visit Betway’s Cheltenham betting page.