The Chester Cup Fact Sheet: A Historic Race with Famous Winners and Jockeys
The Chester Cup is one of the most historic and prestigious horse racing events in the world, held annually at Chester Racecourse since 1824. The race has a long and storied history, with many famous horses, jockeys, and trainers having competed over the years. In this blog post, we’ll take a closer look at the Chester Cup, including its history, notable winners, and legendary jockeys.

History of the Chester Cup
The Chester Cup was first run in 1824 when it was won by Doge of Venice, making it one of the oldest horse races in the world. It was originally called the Tradesman’s Plate before changing to its current title in 1884. The race is run over two miles and two furlongs and is open to horses aged four years and older. Over the years, the race has undergone many changes and modifications, including changes to its distance and eligibility requirements. The most recent change was made in 1992, when it was extended to 2-miles, 2-furlongs and 117 yards to accommodate the starting stalls position. The race is now the feature event of the 3-day Chester May meeting that includes several key trials for the Derby and the Oaks.

Winners
There have been 9 multiple winners of this race, most notably Leamington (1857 and 1859) who went on to become one of the most influential stallions in the early American racing scene and Sea Pigeon (1977 and 1978) who went on to win an Ebor and 2 Champion hurdles at Cheltenham, a feat also matched by Brown Jack after he won in 1931. Anak Pekan was the last horse to land the double when he won the race in 2004 and 2005 under Philip Robinson. Perhaps the most significant winner in recent years came when Trip to Paris won this race in 2015 before he went on to win the Ascot Gold Cup a month later.
There have been many trainers who are synonymous with this race but none more so than Barry Hills, who won this race a record 4 times, with his wins coming in 1980, 1999, 2000 and for the final time in 2009 with Daraahem.
Lester Piggott: Widely regarded as one of the greatest jockeys of all time, Piggott won the Chester Cup an equal record of four times over the course of his career, with has last win coming in 1976 aboard the Jeremy Tree trained John Cherry. He was known for his exceptional skill and strategic racing tactics and was a favourite among fans and fellow jockeys alike. He shares the record with the lesser-known Sam Darling, who won this race four times between 1831 and 1839.
Frankie Dettori: Another legendary jockey, Dettori has won the Chester Cup twice, on Star Player in 1991 and then 28-years later aboard Falcon Eight in 2019. After a long and distinguished career, Dettori has announced that 2023 will be his final year in the saddle and he will be keen to land a third and final Chester Cup as he completes his farewell tour.
Ask any racing fan about the key to backing winners at Chester and they will tell you that it all depends on the draw. The continuous turning nature of the track can make it very difficult to come from off the pace and although it is possible to overcome a wide draw, as Dettori did when winning aboard Falcon Eight in 2019, but it generally pays to look for a horse drawn in the lower half of the stalls.


