May begins with a bang on the racing front. Hot on the heels of the Guineas Festival at Newmarket, fans can look forward to a midweek treat from Chester as the distinctive venue hosts the Boodles May Festival.
Going under starters orders on Wednesday, 7th of May, and concluding on Friday, 9th of May, the track's signature fixture of the year is home to five contests rated at Listed level or above and a clutch of quality handicapping action.
The pick of the handicap contests – and the biggest betting heat of the meeting – comes on the final day, as the historic Chester Cup rolls into action on the Roodee track.
First run over 200 years ago in 1824, this £170,000 event takes place over the 2m2½f trip. Stamina and the ability to race effectively around the extensive turning sections of the course are the order of the day in this event.
The marathon trip appears to partially negate the famous low bias at the track. Over the past ten editions, six winners emerged from stall six or below, but four sprung from box 10 or higher. Nevertheless, we would always suggest taking the draw into consideration. But what else does it take to prevail?
Here, we look at the ten editions of the race between 2014 and 2024 (no race in 2020), highlight the stand-out stats and trends, and pick out our best bets for the 2025 edition.
Fate of the Favourite
The Chester Cup was a graveyard for favourite backers over the ten editions in our sample, with not a single market leader coming home in front. Five winners returned a single-figure SP, with the remaining five priced between 10/1 and 16/1. Montaly (2017) and Making Miracles (2019) were the two runners to score at 16/1.
Breeding Pointers: The Sadler’s Wells Factor
Year | Winner | Sadler's Wells Influence |
2024 | Zoffee | Grandsire to Dam |
2023 | Metier | Great Grandsire to Dam |
2022 | Cleveland | Great Grandsire |
2021 | Falcon Eight | Grandsire |
2019 | Making Miracles | Grandsire to Dam |
2018 | Magic Circle | Dam Sire |
2017 | Montaly | Grandsire |
2016 | No Heretic | Grandsire |
2015 | Trip To Paris | No close relation |
2014 | Suegioo | Grandsire to Dam |
In many handicaps, the most obvious trends appear to jump off the page. In others, locating a pattern amongst the numbers is a little trickier. The Chester Cup falls into that latter category.
However, an interesting pattern did emerge when looking at the pedigrees of the recent winners. As the sire of Galileo, Sadler’s Wells has had a monumental impact on the breed. That influence appears to shine through in this event, with all bar 2015 winner Trip To Paris boasting the name of Sadler’s Wells on their breeding page.
Focusing on those with a healthy dose of Sadler’s Wells blood in their veins in 2025 reduces our list of contenders from 44 to 26.
Up to Winning at this Level
Recent results suggest that if a horse has not previously managed to score at Class 2 level or above, they are unlikely to do so for the first time in this ultra-competitive event.
Focusing on those with a flat win at Class 2 level or above brings our list down to 8.
Age of Winner
The Chester Cup is open to runners aged four and above, and the youngest age bracket boasts a solid record in recent times. At the other end of the spectrum, no horse older than eight has landed the prize in living memory.
The age stat counts against defending champion Zoffee as our list shrinks to seven.
Rating of Winner
Winning off a mark of 90, the 2024 champ Zoffee was the lowest-rated winner in our sample. Dermot Weld’s Falcon Eight topped our ratings list when scoring off 104 in 2021. The average rating of the winner over this period was 97.10, whilst nine of the ten winners ran off a mark of 93 or higher.
Using 93 as our cut-off point sees another four runners bite the dust, leaving only three.
Top Five Finish A Plus
Recent results suggest that those runners who performed at least reasonably well on their most recent racecourse appearance are at an advantage. Whilst only two winners scored last time, five finished in the top three, and eight finished in the top five.
Applying this trend to our remaining runners sees Chemistry and Dawn Rising fall by the wayside, leaving only one.
Other Factors
- Seven of the ten winners had run within the current season.
- Six of ten were at or below their career-high rating.
- Six of the ten winners had nine or fewer starts in turf flat handicaps.
Betting Recommendations: Taipan to Strike for Ireland
Following our analysis, the last horse standing is the Jessica Harrington-trained Taipan. As a son of Frankel, this seven-year-old boasts Sadler’s Wells as his Great Grandsire, has won the equivalent of a Class 2 event in Ireland, gets in off a mark of 98, and finished third behind the 2021 winner of this, Falcon Eight, last time out at Gowran Park.
Encouragingly, the selection also hits all three additional factors. His most recent outing came in April; he was rated 105 in his pomp, and he has eight previous outings in handicaps to his name. With so much in his favour from a trends perspective, he looks worth an early each-way investment.
- Recommended Win Bet: Taipan @ 33/1 with Betfred
Our Top UK Betting Sites for the 2025 Chester Cup:
 (1).webp "10Bet")
Paul Harrison
Falling in love with racing at a young age, Paul’s passion for sports and betting took him to Salford University, where he obtained a Bachelor’s degree in Business Economics with Gambling Studies. Having spent ten years in the employment of a leading bookmaker, Paul opted to go it alone and pursue his dream job as a freelance writer.
