The most winning jockeys and horses of all time at Cheltenham festival

Cheltenham Festival (March 10-13) is upon us. While we get ready for the latest edition of the beloved competition, we can relive its rich history, remembering his most winning jockeys and horses ever and underlining who could realistically shatter their records.

The event will bring together the country’s best jockeys and horses, creating a spectacular competition of talent. Bookmakers are already publishing odds and opinions on the upcoming Festival. In this regard, you can take advantage of the bonuses for Cheltenham at oddschecker, an online comparison site, to minimise losses and place your bets on the most important British event of the horse racing season.

A historic rivalry

In Cheltenham a historic rivalry is renewed every year. Ireland and England compete in the coveted Prestbury Cup, a trophy that is awarded to the nation that wins more than 14 races. The number depends on the total number of challenges, which are 28 at the Festival. The country which wins more races than the other is allowed to lift the cup. Right now, Ireland is leading over England. A good number of historic records and memorable performances in Cheltenham are linked to this heated rivalry.

The most winning jockeys ever

Given the relevance of Cheltenham Festival, it is not surprising that a lot of bright performances happened on that racecourse, where brilliant jockeys challenge one another each and every March. Winning there brings a certain prestige and a huge esteem. It is not by chance that the most winning jockeys in Cheltenham are quite famous in horseracing.

WIth 59 wins in Cheltenham, Ruby Walsh is the greatest jockey to ever race in the Festival. In 2009 and 2016 he won 7 races in a single edition. It means that he alone won 25% of the meeting. In hurdles and fences his win average was through the roof, at about 29% in his prime. He is a legend in horse racing and Cheltenham has long been his favourite stage. 

Barry Geraghty, with 43 wins, was known as the man for the big races in his time. He was famous for giving his best on the biggest stages but never managed to insidiate Walsh in the Festival. A jockey that could hope to achieve the tremendous feat of overtaking Walsh is Paul Townend, with 38 wins in Cheltenham after the 2025 edition. His task won’t be easy but he’s still racing and usually runs like the wind, he is believed to be the only one who could actually beat Walsh’s record.

Horses who dominated in Cheltenham history

Next to the jockeys, we have the horses. It’s not always easy to say if the first or the latter are more relevant in winning a race but, obviously, they must be on the same page in order to meet success. 

Among the fastest racers ever in Cheltenham we find Golden Miller, who won 5 consecutive Gold Cups in the 30s. Of course, it wasn’t the same Festival we have today and a lot of things were different but it is a record and will probably be too difficult to beat with the modern ruleset and the augmented competitiveness of Cheltenham races. In the 60s, horseracing met Arkle, arguably the fastest racer ever, who obviously left his mark also in Cheltenham. The English thoroughbred won 3 Gold Cups, while amassing a lot of other trophies around Great Britain.

As far as legends go, Quevega is one of them. As the first and only horse to win the same race at Cheltenham Festival six years on the trot, Quevega made the Mares’ Hurdle her own prized possession, from 2009 to 2014. Willie Mullins’ mare often made her seasonal reappearance in this race and was a true friend to punters. She never went off shorter than 4/7 during her incredible run of dominance and contributed to creating Mullins’ legacy in Cheltenham. 

The biggest rival of Quevega has been Tiger Roll. He is famous for his back-to-back Aintree Grand National wins in 2018 and 2019, but he is also a five-time Cheltenham Festival winner and a true beacon of versatility. Tiger Roll won the Triumph Hurdle in 2014, and three years later, landed the National Hunt Cup when it was still a true four-miler. He then added three Cross Country wins to his heroics, becoming the darling of the racing public during his best years.

What will happen this year? We are ready to enjoy a new edition of the Festival and, who knows, maybe to add a jockey or a horse to our shortlist of legends. You can follow Cheltenham with us, before and during the event, simply by visiting our site and reading our sports section.