The Chester Cup is one of the oldest handicaps in the racing calendar, first run in 1824 and staged every May over 2m2f on the tight turns of the Roodee. It is also one of the most competitive staying handicaps in Britain, drawing big fields and a record 86 entries in 2026. A Piece Of Heaven took that latest renewal for Joseph O’Brien, the newest name on a roll of honour that stretches back two centuries.
As the feature handicap of Chester’s May meeting, it draws interest well beyond the racecourse and ranks among the most popular contests for horse racing bets each spring. On Cup day it is often the focal point of any punt on this afternoon’s races at the Roodee.
In this article, we run through the last five winners and what each told us about the race.
2026: A Piece Of Heaven
Joseph O’Brien sent three runners to Chester in 2026, and it was A Piece Of Heaven, rather than the better-fancied Puturhandstogether, who came out on top. Dylan Browne McMonagle made the most of a low draw in stall one, sat handy off the pace, and took it up inside the final furlong to beat Maxi King by half a length. A dual-purpose son of Caravaggio, he fitted the profile of a race that increasingly rewards horses with form over both codes.
2025: East India Dock
East India Dock came to Chester in 2025 having just finished third in the Triumph Hurdle at the Cheltenham Festival, switching back to the Flat for the assignment. Trained by James Owen and ridden by Harry Davies, he was the favourite and travelled strongly throughout to win. Owen, in only his third season with a thoroughbred licence, had already become one of the busiest trainers in the country, and the result gave Davies a second straight Chester Cup.
2024: Zoffee
12 months earlier, Davies had won on Zoffee. The eight-year-old, trained locally by Hugo Palmer, had finished second in the 2023 running before going one better, beating Emiyn by three-quarters of a length. It made him one of the few horses to place and then win the Chester Cup in consecutive years.
2023: Metier
Metier’s win in 2023 came under Saffie Osborne for the jumps trainer Harry Fry, another hurdling type taking the prize. Osborne, by then one of the sport’s brightest young riders, judged the finish well to hold off the fast-finishing Zoffee. Metier had been a high-class novice hurdler before finding a new lease of life over staying trips on the Flat.
2022: Cleveland
The run of five begins with Cleveland in 2022, trained by Aidan O’Brien and ridden by Ryan Moore. It was a rare Chester Cup winner for the Ballydoyle stable, and a neat pointer to 2026, when Aidan’s son Joseph took the race himself. Cleveland held off the Andrew Balding-trained Coltrane to give Moore a second win in the race after Suegioo in 2014.
A clear thread runs through these five years. Horses with hurdling form, from Metier to East India Dock, have taken well to the Chester Cup, and the O’Brien family now has its name on the race twice in five runnings.
