Chester Cup – Preview

The Chester Cup is a handicap for four-year-olds and upwards over two and a quarter miles.

It is the feature race of the Chester May meeting and takes place on the closing Friday.

The Chester Cup takes place on the 10th of May 2024.

There have been nine dual winners of the race including Sea Pigeon, Top Cees, Rainbow High and Anak Pekan. Other notable winners in recent years include Overturn and Trip To Paris.

Find out more about the Chester Cup:

Race Overview – The Chester Cup

The Chester Cup is a flat handicap horse race for horses aged four and above.

It is run at Chester racecourse annually in May over a distance of 2 miles and 2 furlongs.

Chester Cup 2025 Odds

Here are the latest odds for the Chester Cup in May 2025:

[justodds event=”chester-cup”]

The betting odds are usually influenced when the draw is made as there is a large draw bias at Chester Races.

Chester Cup Tips

Here are some tips for Chester Cup in May 2025:

• 2 points to win for Novel Legend
• 1 point each way for Israr

Some of the horses participating in the Chester Cup will be spotted in other races throughout the year. Make sure to keep an eye on the horses to see how they perform or place your bets on ante-post betting.

Here is the list of tips for Chester Racecourse Races today from promising shrewd punters who examine key information like the Chester Draw Bias.

Our horse racing tipsters give free betting tips for today’s Chester races.

Chester Cup Previous Winners

Famous Chester Cup Winners

The Chester Cup was established in 1824 and was originally titled the Tradesmen’s Cup. There were three dual winners in the early years; Leamington (1857, 1859), Dalby (1865, 1866) and Pageant (1877, 1878). It did not officially become the Chester Cup until 1884.

Dare Devil (1892, 1893) and Chivalrous (1922, 1923) added their names to the list of dual winners.

The first two-time winner in modern times was Sea Pigeon (1977, 1978). He was an incredibly popular dual-purpose horse best known for his two Champion Hurdle victories in 1980 and 1981. Sea Pigeon also won the 1979 Ebor Handicap under a record top weight of 10 stone. He was eventually retired with 21 victories over jumps and 16 wins on the flat to his credit and is still widely regarded as one of the greatest hurdlers of all time.

Top Cees won the race for Trainer Lynda Ramsden in 1995 and 1997. The first of those victories was shrouded in controversy, leading to a libel case against The Sporting Life for insinuations that the horse had not run to his best in order to protect his handicap mark for the Chester Cup. The Ramsdens won the case and were awarded damages of £195,000.

Rainbow High won for course specialist Trainer Barry Hills in 1999 and 2001. He was well backed on both occasions, defying 9st 13lbs to secure his second victory.

The most recent dual winner was Anak Pekan in 2004 and 2005. He was the heavily-backed 2-1 favourite in 2004 but started at 16-1 when securing back-to-back victories for Trainer Michael Jarvis.

2011 winner Overturn was another popular winner, trained by Donald McCain. He was also a classy hurdler, winning the Galway Hurdle (2010), Ascot Hurdle (2011) and Fighting Fifth Hurdle (2011). He also won the Northumberland Plate on the flat and was runner-up in the 2012 Champion Hurdle at Cheltenham.

Trip To Paris (2015) advanced through the rankings so quickly that he won the Ascot Gold Cup in the same season. Trained by Ed Dunlop, he did not manage to win again after his Ascot triumph but finished a brave second in the Caulfield Cup along with some other good placed efforts.

Key Chester Cup Trials

The Chester Cup always features an intriguing field comprised of established stayers and less exposed four-year-olds.

Those towards the top of the handicap have usually featured in top-staying races such as the Cesarewitch Handicap or Ascot Stakes the previous season.

Previous course form is also a factor, as illustrated by the number of dual winners of this race. It is rare for a horse to improve as rapidly as Trip To Paris did to win the Ascot Gold Cup. However, a win here or a good run under a big weight can lead to entries for the Cup races at Ascot or Goodwood.

Chester Cup Betting Trends

The last eleven Chester Cup favourites have all been beaten. Mamlook won as the 7-1 favourite for David Pipe in 2010 and prior to that you have to go back to Anak Pekan in 2004. Admiral (2006) at 2801 and Bulwark (2008) at 33-1 were major surprises but the longest-priced winners since have been Montaly (2017) and Making Miracles (2019) at 16-1.

There have been three winning four-year-olds in the last seven renewals; Trip To Paris (2015), Making Miracles (2019) and Cleveland (2022).

The oldest winners in modern times have been Sea Pigeon (1978), Morgan’s Choice (1985) and No Heretic (2016) who were successful at the age of eight.

The handicap has become far more compressed in recent years and seven of the last nine winners carried 9 stone or higher. Admiral (2006) with 8st 1lb was the only winner to carry less than 8st 9lbs in the last seventeen renewals.

Chester Cup – Top Trainers and Jockeys

The leading trainer in the history of the Chester Cup is Barry Hills with four winners; Arapahos (1980), Rainbow High (1999, 2001) and Daraahem (2009).

Lynda Ramsden won it three times, twice with Top Cees and also with Travelling Light (1990).

Irish trainers had a poor record in this race prior to the recent victories of Dermot Weld with Falcon Eight (2021) and Aidan O’Brien’s Cleveland (2022).

Two jockeys share the record of four Chester Cup victories; Sam Darling (1831, 1832, 1833 and 1839) and Lester Piggott. The latter was successful aboard Sandiacre (1958), Aegean Blue (1966), Major Rose (1968) and John Cherry (1976).

Betting on the Chester Cup

The Chester Cup is one of the most competitive staying handicaps of the flat season.

Although the record of favourites is poor, most recent winners have featured among the more fancied horses.

There are great opportunities for each-way betting in this race, a thrilling climax to the Chester May meeting.

Summary of Chester Cup

Thank you for reading our Chester Cup guide.

We have looked at stats and facts, betting, tips and more, so you can enjoy the race whether placing a bet or simply watching it.

We highly suggest checking out our list of top Chester Festival Free Bets deals on offer to new customers in May 2025.

Check out our guides to all the other UK Premier Handicap horse races.

Cheshire May Festival Information Articles