Narrowing down the best jockeys in horse racing history is a challenge, but these five sportsmen are legends and have earned their spots on this list of high achievers. These five talented jockeys have raced in some of the most testing and famous competitions the world over. People using betting sites such as Timeform have made lots of money by gambling on these incredible jockeys.

Frankie Dettori

Dettori is one of the most famous jockeys in the world and has earned over 2,500 career wins. Born in Italy, Dettori is the son of a well-known jockey on the Italian circuit, so it stands to reason that coming from a horse racing background would have influenced him. Dettori had earned several awards, tournaments, and meetings throughout his racing career, most notably in 1996, when he won seven out of seven races in one day at the Royal Ascot.

Laffit A. Pincay Jr

Pincay won over 9,500 career wins and was inducted into the National Museum of Racing Hall of Fame in 1975. During his career, he won almost every primary race in the US racing calendar. He won the Hollywood Gold Cup nine times and three consecutive wins in the Belmont Stakes. As a jockey, he was always determined and dedicated and raced with integrity, earning him the title of one of the best jockeys in racing history.

Lester Piggott

Lester Piggott displayed outstanding dedication to the sport and didn’t retire until he was nearly 60. He was born into a long line of jockeys, so it was no surprise that he continued in this career – by ten, he’d started racing horses, and by 12, he’d won his first of many events. Piggott was the youngest jockey to ride more than 100 winners in a single season, and by 18, he’d recorded his first victory in the Epsom Derby. Over his career, he had just under 4,500 career wins, and he won the Ascot Gold Cup 11 times, the St Leger Stakes eight times and the July Cup ten times, among many others.

Cash Asmussen

With over 3000 career wins, Asmussen was a staple fixture in the French racing scene despite being born and growing up in America. He raced in many of the critical competitions in Europe, including the Prix de l’Arc de Triomphe and the Coronation Cup. Between 1982 and 2000, he was based primarily in Chantilly, France, and he was retained as a stable jockey for Stavros Niarchos, a wealthy, stable owner.

Bill Shoemaker

William Shoemaker started racing professionally at 18, winning his first race within a month of first appearing on the track. He raced predominantly on the US circuit and enjoyed over 8,800 wins throughout his career, including all three of the US Classic races on numerous occasions. In 1958, he was given a much-deserved spot in the National Museum and Racing Hall of Fame for his dedication and talents in horse racing.