2025 Chester May Festival: Review

This year’s Chester May Festival, held at the legendary and historic Chester Racecourse, was enthralling and here we are taking a look back at the action across all three days.

The Chester May Festival is a race meeting that attracts horse racing fans in their thousands. The racing is enthralling each year, and the atmosphere and action at the historic and iconic Chester Racecourse was sensational once more this year. The 2025 Festival was most certainly no different, with fans witnessing some enthralling racing action out on the track on each of the three days.

This year’s Chester May Festival took place from Wednesday 7th May to Friday 9th May 2025, where there was a grand total of 21 races took place across a race meeting that is highly anticipated each and every year.

Some of the key races throughout the event included the likes of the Boodles Chester Vase Stakes on day one, followed by the Ladbrokes Big-Value You Can Bet On Ormonde Stakes on Day Two. The standout race on the third and final day of action on Friday 9th May 2025 was, of course, the much anticipated Ladbrokes Chester Cup, which got underway at 15:05 that afternoon.

Here we are going to be taking a look back at all of the enthralling action from all three days of the 2025 Chester May Festival that was held at the legendary and historic Chester Racecourse.

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

We will, of course, start with the opening day of action at this year’s Chester May Festival, which took place back on Wednesday 7th May 2025. The opening race of the day and of the race meeting itself was the CAA Stellar Lily Agnes EBF Conditions Stakes, which was won by the pre-race favourite Ali Shuffle, who was ridden to victory by Jockey Sam Jones.

This race saw Ali Shuffle and Jones fend off some stern competition from the likes of Ray Dawson’s Exclamation and Richard Kingscote’s Italica, who both had to settle for what were second and third place in this race in the end, respectively.

Then came the second of the seven races on the opening day, which was the 2025 edition of the Ladbrokes Best Odds Guaranteed On Racing Handicap at 14:05 that afternoon. The winning jockey on this occasion was Rossa Ryan, who successfully rode the Clive Cox trained Redorange to victory ahead of the runner-up Ruby’s Profit, as well as Cam Hardie’s Blinky, who came in third place to round off the top three.

Race Three of day one at the Chester May Festival for 2025 was the Weatherbys ePassport Cheshire Oaks. The likes of Secret Love and Caspi Star, ridden by David Probert and Silvestre De Sousa’s Caspi Star, were the closest to the winner Minnie Hulk,  ridden by Jockey Ryan Moore, coming in second and third place respectively behind the Aidan O’Brien trained winner overall in the end.

The 2025 edition of the famous Boodles Chester Vase came next, and it was a pre-race favourite who was able to successfully come out on top as the winner, which was Lambourn after being ridden to this victory by Jockey Ryan Moore. This was a second win of the day for both Moore and trainer Aidan O’Brien.

The Love Federal Capital Handicap was the third to last race of the opening day, where the pre-race favourite, Bob Mali, had to settle for what was a 4th place finish and just outside of the top three in the end. The winner was Tom Eaves on board Hammer The Hammer, followed by Saffie Osborne’s Diligently and Hollie Doyle’s Cyclonite in second and third place, respectively.

Race six was the latest running of the Heineken Maiden Stakes at Chester Racecourse. The pre-race favourite failed to win the race again, with Mariner coming home down in 4th with Jockey Robert Havlin.

The winner was Tom Marquand on board the Alan King trained horse Daiquiri Bay, who secured the victory ahead of the runner-up Mister Winston, ridden by David Probert, as well as William Buick on board Criminal, who came in third overall.

Race seven, the final one on the day, was the 2025 Horseradish Catering & Events Handicap at 16:45 on that Wednesday evening. The winner was a Jennie Candlish trained Probe, who, whilst being ridden for jockey Kieran O’Neill, emerged victorious with second place being secured by Rossa Ryan onboard Supreme King, whilst Oliver Stammers and The Turpinator had to settle for what was a third place finish in the end.

We will now move on to the action that took place on day two of the 2025 Chester May Festival – Ladies Day, which took place this year on the afternoon of Thursday 8th May 2025.

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

The race that opened Ladies Day at this year’s Chester May Festival was the latest running of the CAA Stellar Handicap, which was won by Oisin Murphy and Roman Dragon, whilst Warren Fentiman’s Rosenpur came home in second place overall in the end. Tom Marquand and Balmoral Lady rounded off the top three in third place.

This was then followed by the 2025 British Stallion Studs EBF Maiden Stakes, which got underway at 14:05 on this Thursday afternoon. This race saw the pre-race favourite win for the first time on Day Two, with Oisin Murphy riding Tricky Tel home to victory ahead of the likes of Call Me By My Name and Senorita Vega in second and third place respectively, with these horses being ridden by Jockeys Billy Loughnane and Richard Kingscote.

The third race to take place on Ladies Day was the Boodles Raindance Dee Stakes, where it was another victory for the pre-race favourite. This time it was Mount Kilimanjaro who was the winner with the Aidan O’Brien trained horse finishing ahead of runner-up High Stock in second place, whilst it was Tom Marquand and Great David who came in third place overall, in the end.

Race four of Ladies Day at Chester for 2025 was to be the latest running of the Ladbrokes Big-Value You Can Bet On Ormonde Stakes, which was one of the standout races of the day itself and of the race meeting as a whole. Pre-race favourite was Ryan Moore on board Illinois, whilst it was Al Qareem and Absurde who came home in third.

Then came the fifth race of Thursday afternoon, which was the Louise Keegan Handicap. Jim Crowley’s El Burhan, the pre-race favourite, came out on top as the winner, followed by runner-up God Of War, whilst Sweet Fantastic (ridden by Jockey James Sullivan) came home to round off the top three in this race in third place.

The penultimate race of Ladies Day was the Halliwell Jones Handicap, where the pre-race favourite Box To Box ended up finishing down in seventh place. Instead, it was a superb performance from Andrew Mullen and Paddy The Squire, winning the race after successfully fending off some stern competition from the likes of David Allan’s Austrian Theory in second place and Billy Loughnane’s Fouroneohfever in third place.

The final race of the day was the 2025 Oxford Natural Handicap, which was won by the pre-race favourite Lady Vivian, trained by Ralph Beckett and with Jockey Hector Crouch on board in what was a superb performance. Way Of Stars came in second place, whilst it was Patagonia Girl who settled for a third place finish in the end.

We are now going to take a look ahead at the third and final day of the 2025 Chester May Festival, which took place back on Friday 9th May 2025, where seven races took place throughout that afternoon at the historic Chester Racecourse.

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

The final day of the 2025 Chester May Festival features arguably the most famous race of the entire meeting – the highly coveted Ladbrokes Chester Cup, which is the race that day three is named after. Chester Cup Day at Chester Racecourse took place back on the afternoon of Friday 9th May 2025, with seven races taking place.

The action on this day opened with the CAA Stellar Earl Grosvenor Handicap. The pre-race favourite, Two Tempting, was the horse that came out on top thanks to a superb performance from Jockey Rob Hornby in what was also a victory for trainer Jonathan Portman. Warren Fentiman’s Partisan Hero and Richard Kingscote’s Kindest Nation came in second and third place, respectively, to fill what were the final two spots in the race’s top three.

It was to be the 2025 Boodles Darley EBF Maiden Stakes which came next, and this time it was not the pre-race favourite who won, with Ryan Moore’s The Pouncing Lion having to settle for what was a 6th place finish in the end. Instead, it was David Probert and Al Wasl Storm who came out on top as the winner, with the Owen Burrows trained horse coming home ahead of the likes of Tom Marquand’s Orionis and Harry Davies’ Ammes in second and third place.

Race Three of Chester Cup Day was indeed the latest running of the Ire-Incentive, It Pays To Buy Irish Huxley Stakes came next, and it was the pre-race favourite The Foxes who won thanks to a superb ride from Jockey Oisin Murphy, followed by Cairo in second place, whilst it was Ryan Moore’s Liberty Lane who came in third place in the end.

Then came the main event of the day and the most famous race of the entire race meeting – the 2025 Ladbrokes Chester Cup. The Jockey to add his name to the history books was Harry Davies, who rode a James Owen trained East India Dock to victory in the end, ahead of the likes of Callum Shepherd’s Caballo De Mar in second and Joe Leavy’s Zoffee in third place.

The third to last race of the day, the fifth to take place overall, was the latest running of the Precision Facades Handicap. With the pre-race favourite Warda Jamila, ridden by Oisin Murphy, coming down in seventh place, with it being Warren Fentiman and Let’s Dream coming out on top as the winners ahead of runners-up Auld Toon Loon in second place and Rathgar in third.

Race number six of the 2025 Chester Cup Day was the Xenon Workplace Apprentice Handicap, with it being the pre-race favourite in the form of Ashley Lewis’ Small Fry being the winner of this race, just ahead of the runner-up Sportingsilvermine and ahead of Giselles Defence in third place overall.

The seventh race on the afternoon of the last day, the Ladbrokes Get Rewarded With Ladbucks Chester Plate Handicap, was won by Darren Fentiman on board Gibside, who was trained by Tim Easterby. It was the pre-race favourite, Surrey Bell, who came home in second place, with Callum Shepherd’s Artisan Dancer coming in third.

Excitement is already building ahead of the action to come in the 2026 Chester May Festival next year that is set to get underway at the legendary Chester Racecourse over the course of three days, taking place from Wednesday 6^th May to Friday 8^th May 2026 – these dates are yet to be confirmed.

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