Top 5 Best Jockeys of all time - Eventmasters Hospitality (2024)

So many incredible jockeys have graced racecourses across the world over the years, and here are just some of the best in the history of horse racing.

The sport of horse racing has a tremendous history stretching back hundreds of years and many generations. The United Kingdom is home to some of the oldest racecourses in the world, including Ascot, Cheltenham, Aintree, Newmarket, Sandown and York.

Over the years, there have been a number of legendary horses, jockeys and trainers that have battled with their competitors for some of the most prestigious titles in the sport, including the likes of Royal Ascot, the Epsom Derby, the York Dante and Ebor Festivals, as well as the QIPCO British Champions Day at Ascot.

This post focuses on the many legendary jockeys that have graced the sport over the years, and there are too many icons of horse racing to name here. So, in light of this, we decided to look at five of the best jockeys of all time, starting with Bill Shoemaker at 5.

5 – Bill Shoemaker

The late, great Bill Shoemaker is the first legendary jockey that we will mention here, and he is, as of the time of writing, the fifth most successful jockey of all time. The American won no less than 8,883 races in what was an extraordinary 41 year career. His retirement finally came in 1989, and at this point, it is thought that Shoemaker had won approximately $120 million in prize money before earning $3.7 million as a trainer.

Just some of Shoemaker’s major wins have come in the Kentucky Derby (4 – 1955, 1959, 1965 & 1986), the Belmont Stakes (5 – 1957, 1959, 1962, 1967 & 1975), the Preakness Stakes (2 – 1963 & 1967) and the Breeders’ Cup Classic (1987).

4 – Frankie Dettori

Italian jockey Frankie Dettori is an icon of horse racing, and he took part in his final British Champions Day at Ascot in October 2023. Dettori has won the Prix de l’Arc de Triomphe – the most of any jockey. He also rode Godolphin for 20 years, and his other mounts include the legendary Stradivarius and Enable.

Out of 2,469 starts, Frankie Dettori has 533 wins, 382 second-place finishes and 294 third-place finishes.

3 – Ruby Walsh

It is safe to say that Ruby Walsh had a highly successful career spanning multiple decades in this sport. Not only did Walsh have no less than 2,500 career race wins, the Irishman is also the most successful jockey at the Cheltenham Festival of all time with 59. Walsh is 16 clear of Barry Geraghty with 43 and 28 ahead of Tony McCoy in third place with 31 to his name.

Walsh retired in 2019 after sealing his 213th win in a Group One race.

2 – Lester Piggott

Lester Piggott is synonymous with horse racing, and it is no surprise to see him in the top two of this list. He had no less than 30 Classic triumphs, with 5 2,000 Guineas wins, 2 1,000 Guineas wins, 9 Epsom Derby wins, 6 Epsom Oaks wins, and 8 St. Leger wins. The Englishman also has a Prix de l’Arc de Triomphe success and two wins in the Irish Derby.

By the time he retired as a jockey in 1995, Lester Piggott had more than 4,400 race wins.

1 – Sir Anthony McCoy

This list finishes with Sir Anthony McCoy, who is also widely seen as one of horse racing’s best-ever jockeys. To start with, McCoy is the only jockey to date to have been awarded the BBC’s Personality of the Year Award, which he received in 2010. He was also named as flat racing’s Champion Jockey for no less than 20 consecutive years (this was in every year in which he was a professional jockey!).

On top of this, he had more than 4,300 race wins in his career. This includes 31 wins at the Cheltenham Festival, where he won the Albert Bartlett Novices’ Hurdle 3 times (Black Jack Ketchum – 2006, Wichita Lineman – 2007 & Fishers Cross – 2013), the Champion Hurdle 3 times (Make A Stand – 1997, Brave Inca – 2006 & Binocular – 2010).

He also won the Cheltenham Gold Cup twice (Mr Mulligan – 1997 & Synchronised – 2012) and the Grand National once, onboard Don’t Push It in 2010.

In the next few years, it will be interesting to see who will be making history and if any jockey can seal their legendary status alongside the iconic names mentioned on this list.

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