2025 Chester May Festival: Preview

The annual Chester May Festival is one of the standout horse racing meetings of the year, and there is plenty of anticipation ahead of the 2025 edition of this highly prestigious event at Chester Racecourse.

Opening back in 1539, Chester Racecourse is the oldest racecourse that is still in operation anywhere in the world, which is extraordinary, as is the annual Chester May Festival hosted at this historic venue this week.

The 2025 Chester May Festival will be taking place over three days, taking place from Wednesday 7th May to Friday 9th May 2025.

A total of 21 high quality races are taking place across all days at this year’s event, and it is set to be a spectacular spectacle for all horse racing fans in attendance. The race that probably stands out the most is the Chester Cup, which will, of course, be taking place on Friday 9th May, which will be the third and final day of this year’s Festival at Chester.

This year’s race will be taking place at 15:00 on Friday. The most recent winner of this race is Zoffee, with the Hugo Palmer trained horse being ridden to victory by jockey Harry Davies after fending off some stern competition from the likes of Zak Wheatley’s Emiyn and Richard Kingscote’s Zanndabad, who had to settle for a second and third place finish overall in the end.

Here, we are going to be taking a look at all of the action to come in this year’s edition of the famous Chester May Festival that is to be held by the even more historic and iconic Chester Racecourse this week.

Boodles May Festival City Day – Wednesday 7^th May 2025

Starting with the first day on Wednesday 7^th May 2025, this has seven races taking place, as will the other two days of this horse racing event at Chester.

The first race of the day will be the 13:30 CAA Stellar Lily Agnes EBF Conditions Stakes, won last year by Seraphim Angel, ridden by Jockey Pierre-Louis Jamin, followed by the runner-up, which was the pre-race favourite Flicka’s Girl.

Next up will be the Ladbrokes Best Odds Guaranteed On Racing Handicap, with the pre-race favourite being Redorange, trained by Clive Cox. It will be taking place at 14:05 on Wednesday afternoon.

Following this race will be the 14:35 Weatherbys ePassport Chesire Oaks, and then the Boodles Chester Vase Stakes will be taking place at 15:05, which were won last year in 2024 by William Buick on board Hidden Law.

Then comes the 15:40 Love Federal Capital Handicap, which is followed by the 16:10 Heineken Maiden Stakes, which is also the penultimate race of the opening day of the 2025 Chester May Festival.

The seventh and final race taking place on day one of this fantastic festival is the 16:45 Horseradish Catering & Events Handicap, which was won most recently back in 2024 by Divine Libra, who managed to fend off some stern competition from the likes of runner-up He’s A Gentleman as well as from Evocative Spark, who came down in third place to round off the top three.

Boodles May Festival Ladies Day – Thursday 8^th May 2025

Next up is the second and penultimate day of the 2025 Chester May Festival – Ladies Day – which is going to be taking place in the form of seven races that are held throughout the afternoon of Thursday 8th May 2025.

The 2025 edition of the CAA Stellar Handicap is set to get proceedings underway for day two, with 12 horses, jockeys, and trainers eager to come out on top as the latest winner of this race. The winner back in 2024 was the pre-race favourite Democracy Dilemma, ridden by Tom Marquand, followed by runners-up Copper Knight and Vintage Clarets, who came down in third place to round off the top three in the race.

Then comes the 14:05 British Stallion Studs EBF Maiden Stakes as the second race of Ladies Day at Chester Racecourse on Thursday afternoon. After that is the 14:35 Boodles Raindance Dee Stakes, followed by the 15:05 Ladbrokes Big Value You Can Bet On Ormonde Stakes.

The Louise Keegan Handicap, taking place at 15:40, is set to be the third to last race of the day, where 9 runners will be vying for glory.

There will then be a bumper race involving no less than 14 runners, who will all be looking to become the latest winners of the Halliwell Jones Handicap race, won last year by the pre-race favourite Never So Brave, ridden by jockey Ryan Moore. Daniel Tudhope’s Witness Stand came in second place, whilst James Doyle’s Dashing Darcey came in third place.

The seventh and final race of the day is going to be the 2025 version of the Oxford Natural Handicap, which will be taking place from 16:45 on Thursday afternoon. Last year’s race was won by pre-race favourite Fouroneohfever, ridden to victory by Jockey William Buick.

Boodles May Festival Ladbrokes Chester Cup Day – Friday 9^th May 2025

We are now moving on to the third and final day of the 2025 Chester May Festival, which is going to be the much anticipated Chester Cup Day, taking place on the afternoon of Friday 9th May 2025, with the final seven races being run at Chester Racecourse.

Action on day three is getting underway with the 2025 CAA Stellar Earl Grosvenor Handicap, taking place at 13:30 on Friday afternoon. Last year’s winner in this particular race was Percy’s Lad, who was ridden by Jockey Richard Kingscote, with him able to beat some fierce competition from the likes of the pre-race favourite Dancing Magic in second place, whilst it was Silvestre De Sousa who came home in third place on board Documenting, who came in third overall.

The 14:05 Boodles Darley EBF Maiden Stakes then comes next, which is then followed by the third race of the day, which will be the Ire-Incentive, It Pays To Buy Irish Huxley Stakes that is a race that is going to be run at 14:35 on Thursday afternoon.

Then comes one of the standout races of the entire meeting, which will be the 2025 edition of the highly prestigious Ladbrokes Chester Cup at 15:05 on Thursday. The honour of being the jockey with the most wins belongs to both Sam Darling and the legendary Lester Piggott.

Darling won with Independence (1831), Colwick (1832), Pickpocket (1833, and Cardinal Puff (1839), whilst Piggott’s Chester Cup wins came with the likes of Sandiacre (1958), Aegean Blue (1966), Major Rose (1968), and John Cherry (1976).

Fast forward to 2024, and the most recent winner of the Chester Cup was Zoffee, ridden by Harry Davies and trained by Hugo Palmer.

After more history is made in the Chester Cup with the 2025 winner being crowned, the fifth race of the day, the 15:40 Precision Facades Handicap will be taking place, followed by the sixth and penultimate race of the day, which is going to be the Xenon Workplace Apprentice Handicap, which will be run at 16:10 on Thursday afternoon.

Then came the seventh and final race of the day, the Ladbrokes Get Rewarded With Ladbucks Chester Plate Handicap, which is also going to be the last race of the 2025 Chester May Festival as a whole at the legendary Chester Racecourse, with no less than 11 Runners vying for glory in this race.

Excitement is building rapidly ahead of the action that is set to get underway at the legendary Chester Racecourse when the 2025 edition of the highly prestigious Chester May Festival gets underway on Wednesday 7th May 2025.

All eyes will be on the action out on track as we get to see some enthralling racing at one of the most historic horse racing venues in the country. The 2025 Chester May Festival will be taking place over the course of three days, from Wednesday 7th May 2025 to Friday May 2025, which of course features the iconic and highly coveted Chester Cup.

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