Cheshire Oaks Preview, Tips, Runners & Trends (May Meeting)

Explore the history of the Cheshire Oaks, a race staged over 1m3½f at Chester during the May Meeting. We detail trainer and jockey achievements from previous renewals while highlighting statistical patterns that have emerged to influence the race's likely outcome.
Cheshire Oaks Preview, Tips, Runners & Trends (May Meeting)
Andy Powell
Andy Powell Expert Guide

You know how punters get lost in too much data or bet blindly? I break down the stats and trends so you can feel confident you’re betting with more than just gut instinct.

2026 Cheshire Oaks Preview

Scheduled to take place at Chester during the May Meeting is the Listed Cheshire Oaks, the race is open to three-year-old fillies only and is run over a trip of one mile, three furlongs and seventy-five yards. Established in 1950, the race can serve as a trial for the Epsom Oaks. Enable (2017) is a runner who won both races.

For sponsorship purposes, the 2026 renewal of the Cheshire Oaks will hold the title of 'Weatherbys Cheshire Oaks'.

Cheshire Oaks Information:

Why not use the trends shortlist below to help you narrow down the field and then head over to the dedicated Chester tips page to see which runners are being supported by the OLBG expert racing tipsters to find yourself a bet? You may also be interested in other preview blogs that we have packed full of information. Head down to the Other Principal races during the Chester May Meeting section for links to these.

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How competitive is the Cheshire Oaks market? When looking at the over-rounds for the last 20 renewals, the most competitive market was in 2005, when the race had an over-round of 110%. The race in 2016 was a race that was most in the bookie's favour with an over-round of 123%, whilst on average over the last 20 renewals of the Cheshire Oaks, the over-round has been 115%, which means the bookie expects to pay out ÂŁ100 for every ÂŁ115 which is bet.

Below you will find the 2026 Cheshire Oaks Trends. See which patterns have occurred over the recent renewals that you may be able to use for the next renewal. We also have a section that looks at the Cheshire Oaks Trend Analysis. With the field now finalised, we have the Cheshire Oaks Trend Shortlist, which is created using the listed trends.

These are the top three quickest-run Cheshire Oaks races over the last 20 renewals:

  1. Perfect Truth (2:22.17) in 2009
  2. Light Shift (2:22.99) in 2007
  3. BanoffeeI (2:23.77) in 2013

Looking at the future form, is the winner worth following next time out? Over the past 20 renewals, if you had followed the winner of the Cheshire Oaks next time out, then you would have backed a total of 3 winners. Backing all 20 runners who have been out since their win at SP next time out would have returned an LSP of +0.00. Whilst we wait for the 2026 Cheshire Oaks, remember you can get daily racing predictions from the expert tipsters on the racing predictions page.

When looking over the past 20 renewals, a time of 2:22.17 was set by Perfect Truth in 2009, trained by A P O'Brien and ridden by Johnny Murtagh, which is the quickest time over that period. The slowest winning time was set in 2023 when Savethelastdance won in a time of 2:36.64 for trainer A P O'Brien, who booked Ryan Moore in the saddle.

What the expert says...
Between 2006 and 2024, every winner bar Good Morning Star (2012) went on to run in the Epsom Oaks next time out, Light Shift (2007) and Enable (2017) went on to win the Oaks, but it has been limited success.

Andy Powell - Horse Racing Betting Expert - OLBG.com

Cheshire Oaks Past Winners

Here are the Cheshire Oaks past winners for the last 10 renewals. Each row details the race year, the winning horse, and the horse's age & weight. Also detailed is the stall from which the horse came and the total number of runners in the race. The horse's trainer and the jockey at the time of winning the Cheshire Oaks are also displayed, along with the starting price at which the horse was sent off.

YearHorse (Drawn)Info
2025
2:29.15
Minnie Hauk (IRE)
3yo 9-2 (6 of 7) 13/8F
Ryan Moore
A P O'Brien (IRE)
2024
2:28.27
Forest Fairy (IRE)
3yo 9-2 (1 of 6) 11/4
Rossa Ryan
Ralph Beckett (GB)
2023
2:36.64
Savethelastdance (IRE)
3yo 9-2 (5 of 8) 8/11F
Ryan Moore
A P O'Brien (IRE)
2022
2:31.64
Thoughts Of June (IRE)
3yo 9-2 (8 of 9) 7/1
Ryan Moore
A P O'Brien (IRE)
2021
2:32.72
Dubai Fountain (IRE)
3yo 9-0 (3 of 7) 13/8F
Franny Norton
Mark Johnston (GB)
2019
2:31.51
Mehdaayih (GB)
3yo 9-0 (6 of 11) 3/1F
Robert Havlin
John Gosden (GB)
2018
2:28.61
Magic Wand (IRE)
3yo 9-0 (1 of 10) 3/1F
Ryan Moore
A P O'Brien (IRE)
2017
2:23.80
Enable (GB)
3yo 9-0 (3 of 7) 2/1
Frankie Dettori
John Gosden (GB)
2016
2:29.05
Somehow (IRE)
3yo 9-0 (6 of 8) 8/15F
Ryan Moore
A P O'Brien (IRE)
2015
2:30.34
Diamondsandrubies (IRE)
3yo 9-0 (2 of 10) 5/4F
Ryan Moore
A P O'Brien (IRE)

Where have the winning runners come from?

Here are the countries where the winning trainers of the Cheshire Oaks have been based:

  • GB: 11 winners with an additional 26 placings from 141 runners
  • IRE: 9 winners with an additional 7 placings from 29 runners
  • FR: 0 winners with an additional 0 placings from 2 runners

2025 Cheshire Oaks Replay


Cheshire Oaks Trainer Statistics

The leading trainer in the Cheshire Oaks over the last 20 renewals is A P O'Brien, who has won the race nine times, with those nine winners coming from Sail (2008), Perfect Truth (2009), Wonder Of Wonders (2011), Diamondsandrubies (2015), Somehow (2016), Magic Wand (2018), Thoughts Of June (2022), Savethelastdance (2023) and Minnie Hauk (2025).

Here are the Cheshire Oaks trainer statistics over the last 20 renewals for trainers who have entries in the 2026 renewal; those not listed have not had a runner. (R = Runners, W = Winners, P = Places including winners, Win LSP is based on 1pt Win and EW LSP is based on 0.5pt Win & 0.5pt Place):

TrainerR-W-PWinEW
A P O'Brien19-9-14+16.59+10.70
Ralph Beckett11-1-4-7.25-5.58
Andrew Balding8-0-2-8.00-5.22
John & Thady Gosden4-0-0-4.00-4.00

Cheshire Oaks Jockey Statistics

The leading jockey in the Cheshire Oaks over the last 20 renewals is Ryan Moore, who has won the race seven times, with those seven winners coming from Wonder Of Wonders (2011), Diamondsandrubies (2015), Somehow (2016), Magic Wand (2018), Thoughts Of June (2022), Savethelastdance (2023) and Minnie Hauk (2025).

Here are the Cheshire Oaks jockey statistics over the last 20 renewals for jockeys who have rides in the 2026 renewal; those not listed have not had a runner. (R = Runners, W = Winners, P = Places including winners, Win LSP is based on 1pt Win and EW LSP is based on 0.5pt Win & 0.5pt Place):

JockeyR-W-PWinEW
Ryan Moore
(Amelia Earhart)
17-7-10+5.34+2.31
William Buick
(Im The One)
7-1-3-3.50-1.99
Oisin Murphy
(Winged One)
8-0-2-8.00-4.80
James Doyle
(A La Prochaine)
7-0-1-7.00-4.50

Cheshire Oaks Trend Shortlist

Chester will host the 2026 renewal of the Cheshire Oaks, which will be run at 2:35 pm on Wednesday, 6th May 2026, and these are the runners who perform best based on the trends, along with the trainer, jockey and their record in the race (Runs-Wins-Places Win LSP / EW LSP):

  • 15/15 Im The One (8/11)
    • John & Thady Gosden (4-0-0 -4.00 / -4.00)
    • William Buick (7-1-3 -3.50 / -1.99)

Others: A La Prochaine (14/15), Amelia Earhart (14/15), Winged One (13/15) and Sugar Island (13/15).

*Trainer & Jockey numbers are Runs-Wins-Places Win LSP / EW LSP, Runners, Odds and Trends Passed/Failed correct at the time of posting (11:53 am Monday 4th May 2026), if no odds were available at the time of posting, then forecasted odds are used.

Cheshire Oaks Trend Analysis

✅ The trend factor, which has produced 10+ winners and shows the best LSP, an LSP of +58.34, is when runners ran in a race restricted to 3yo when last winning.

❌ The worst performing factor that has failed to produce a single winner is when runners had 0 career places in Non-Handicap, when backing these, the trend shows a record of 0-19.

Here are the most recent winning draws, along with the further placings in brackets:

  • 2025: Winner in 6 (1) [7 Runners]
  • 2024: Winner in 1 (9) [6 Runners]
  • 2023: Winner in 5 (2,3) [8 Runners]
  • 2022: Winner in 8 (7,4) [9 Runners]
  • 2021: Winner in 3 (7) [7 Runners]

The course which has produced the most winners of the Cheshire Oaks is Leopardstown; there have been a total of 6 winners of this race who ran at Leopardstown last time out. The next best course, which has produced the second most winners, is Newbury; there have been a total of 5 winners of this race who ran at Newbury last time out.

Looking over the past renewals, these are the stallions whose offspring have produced multiple winners of the Cheshire Oaks:

  • Galileo (4 Wins)
  • Fastnet Rock (2 Wins)
  • Frankel (2 Wins)
  • Kingmambo (2 Wins)
  • Sadlers Wells (2 Wins)

Looking over the past renewals, there is only one stallion whose offspring have been disappointed with multiple attempts but no wins in the Cheshire Oaks; that stallion is Singspiel, who has failed to produce a winner from 6 runners.

Looking at the winning odds over the last 20 renewals, the biggest-priced winner was Good Morning Star in 2012, winning for Mark Johnston at odds of 50/1 under the guidance of Franny Norton. Looking at the runners at the head of the market over the last 20 renewals, there have been 13 winning favourites in the race. Whilst we wait for the 2026 Cheshire Oaks, remember you can get daily racing predictions from the top racing tipsters on the best racing tipsters page.

Route to the Cheshire Oaks

Many trainers target races as preparation for the Cheshire Oaks. These are the races which the recent winners ran in before coming here:

InfoLast Race
2025 - Minnie Hauk
Leopardstown - 1st of 9 (2/5)
Irish Stallion Farms EBF Fillies Maiden
2024 - Forest Fairy
Wolverhampton (AW) - 1st of 7 (10/3)
Stay Golden With BetMGM Safer Gambling Novice Stakes
2023 - Savethelastdance
Leopardstown - 1st of 10 (20/1)
Irish Stallion Farms EBF Fillies Maiden
2022 - Thoughts Of June
Leopardstown - 2nd of 12 (5/1)
Irish Stallion Farms EBF Fillies Maiden
2021 - Dubai Fountain
Newmarket (Rowley) - 4th of 10 (16/1)
Fillies Mile
2019 - Mehdaayih
Chelmsford (AW) - 1st of 2 (1/4)
Buy Tickets At chelmsfordcityracecourse.com Fillies Handicap
2018 - Magic Wand
Leopardstown - 3rd of 8 (7/2)
Irish Stallion Farms EBF Fillies Maiden
2017 - Enable
Newbury - 3rd of 6 (5/1)
Dubai Duty Free Golf World Cup EBF Stallions Conditions Stakes
2016 - Somehow
Leopardstown - 1st of 12 (15/8)
Irish Stallion Farms European Breeders Fund Fillies Maiden
2015 - Diamondsandrubies
Navan - 3rd of 9 (5/2)
Irish Stallion Farms European Breeders Fund Salsabil Stakes

Other Principal races during the Chester May Meeting

Remember to head over to the Chester predictions page to see which runner the racing tipsters are supporting in the Cheshire Oaks. Below are the other principal races that we cover during the May Meeting, with links to each race blog as well as information for last year's winners.

RaceLast WinnerInfo
Cheshire Oaks
Wednesday
Minnie Hauk (IRE)
3yo - 13/8
A P O'Brien
Ryan Moore
Chester Vase
Wednesday
Lambourn (IRE)
3yo - 11/8
A P O'Brien
Ryan Moore
Dee Stakes
Thursday
Mount Kilimanjaro (FR)
3yo - 1/1
A P O'Brien
Ryan Moore
Ormonde Stakes
Thursday
Illinois (IRE)
4yo - 6/5
A P O'Brien
Ryan Moore
Huxley Stakes
Friday
The Foxes (IRE)
5yo - 13/8
Andrew Balding
Oisin Murphy
Chester Cup
Friday
East India Dock (GB)
4yo - 9/4
James Owen
Harry Davies

Article Contributor Information

We are fortunate to have an excellent team of specialists and experts at OLBG. Contributing to the creation and maintenance of this Cheshire Oaks Preview are Andy and James. They both work on the Horse Racing Tips team, overseeing the tipsters and managing the tip settlement, while also creating and managing all the horse racing event previews for Flat racing.

James Banting

James Banting

Expert Guide

James Banting, a passionate horse racing enthusiast and aficionado, brings a wealth of experience to OLBG, having attended numerous race meetings over the years. His background working with the Jockey Association provides him with a unique insider's perspective on the industry.
Andy Powell

Andy Powell

Expert Guide

Andy, a seasoned horse racing expert with over 15 years of experience, possesses a comprehensive understanding of the sport, from delving into complex statistical data for flat racing in the UK and Ireland to crafting insightful flat racing blogs for OLBG.

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