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.
2027 Chesterfield Cup Handicap Preview
Run during the Glorious Goodwood festival in July of each year at the Goodwood Racecourse is the Chesterfield Cup Handicap. This is a Class 2 handicap that is run over a trip of one mile and two furlongs and is open to runners who are aged four or older.
Chesterfield Cup Handicap Information:
- Chesterfield Cup Handicap Past Winners
- Chesterfield Cup Handicap Trainer Statistics
- Chesterfield Cup Handicap Jockey Statistics
Our dedicated Goodwood tips page will not only bring you predictions from the OLBG racing tipsters for the upcoming card that includes the Chesterfield Cup Handicap, but will also have predictions for each meeting at Goodwood throughout the season, so be sure to head over there. You may also be interested in other preview blogs that we have packed full of information. Head down to the Races Covered at Glorious Goodwood section for links to these.
Best Horse Racing Betting Sites 2026
How competitive is the Chesterfield Cup Handicap market? When looking at the over-rounds for the last 20 renewals, the most competitive market was in 2021, when the race had an over-round of 114%. The race in 2026 was a race that was most in the bookie's favour with an over-round of 134%, whilst on average over the last 20 renewals of the Chesterfield Cup Handicap, the over-round has been 125%, which means the bookie expects to pay out £100 for every £125 which is bet.
Below you will find the 2027 Chesterfield Cup Handicap 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 Chesterfield Cup Handicap Trend Analysis.
These are the top three quickest-run Chesterfield Cup Handicap races over the last 20 renewals:
- Sennockian Star (2:02.84) in 2014
- Fire Fighting (2:03.60) in 2016
- Mount Logan (2:04.94) in 2015
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 Chesterfield Cup Handicap next time out, then you would have backed a total of 5 winners. Backing all 19 runners who have been out since their win at SP next time out would have returned an LSP of +13.85. Remember to use the racing predictions along with the information on this page to find a bet on the 2027 Chesterfield Cup Handicap.
The runner that holds the record over the past 20 renewals for the slowest time in the race was set in the 2021 renewal when Migration from David Menuisier under the guidance of William Buick, won in a time of 2:13.30, whilst at the other end of the spectrum, Sennockian Star, trained by Mark Johnston and ridden by Joe Fanning set the quickest time of 2:02.84 in the 2014 renewal.
What the expert says...
Andy Powell - Horse Racing Betting Expert - OLBG.com
Chesterfield Cup Handicap Past Winners
Here are the Chesterfield Cup Handicap 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 Chesterfield Cup Handicap are also displayed, along with the starting price at which the horse was sent off.
| Year | Horse (Drawn) | Info |
|---|---|---|
| 2026 2:06.20 | Al Aali (FR) 4yo 8-10 (3 of 17) 11/2F | William Buick George Scott (GB) |
| 2025 2:05.12 | Westridge (FR) 4yo 8-8 (8 of 18) 6/1 | Billy Loughnane John & Thady Gosden (GB) |
| 2024 2:06.23 | Take Heart (IRE) 4yo 9-2 (18 of 17) 7/1 | Ben Coen J P Murtagh (IRE) |
| 2023 2:09.90 | Ancient Rome (USA) 4yo 9-7 (16 of 15) 33/1 | Jamie Spencer Charles Hills (GB) |
| 2022 2:05.31 | Forest Falcon (IRE) 4yo 9-1 (16 of 18) 14/1 | Frankie Dettori Charlie & Mark Johnston (GB) |
| 2021 2:13.30 | Migration (IRE) 5yo 8-10 (14 of 11) 2/1F | William Buick David Menuisier (GB) |
| 2020 2:06.97 | Maydanny (IRE) 4yo 8-6 (1 of 18) 5/1F | Silvestre De Sousa Mark Johnston (GB) |
| 2019 2:09.26 | Fayez (IRE) 5yo 8-12 (11 of 16) 25/1 | Daniel Tudhope David O'Meara (GB) |
| 2018 2:08.50 | Alfarris (FR) 4yo 9-0 (3 of 15) 13/2F | Jim Crowley William Haggas (GB) |
| 2017 2:07.79 | Fabricate (GB) 5yo 9-4 (6 of 16) 20/1 | Adam Kirby Michael Bell (GB) |
Where have the winning runners come from?
Here are the countries where the winning trainers of the Chesterfield Cup Handicap have been based:
- GB: 19 winners with an additional 55 placings from 320 runners
- IRE: 1 winner with an additional 0 placings from 5 runners
- HK: 0 winners with an additional 0 placings from 1 runner
2026 Chesterfield Cup Handicap Replay
Chesterfield Cup Handicap Trainer Statistics
Multiple trainers have not had the best of times over the last 20 renewals in the Chesterfield Cup Handicap. Saeed bin Suroor (0-13), Richard Fahey (0-11) and William Knight (0-10) have all failed to produce a single winner despite sending multiple runners to the race.
Here are some of the top Chesterfield Cup Handicap trainer statistics over the last 20 renewals (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):
| Trainer | R-W-P | Win | EW |
|---|---|---|---|
| Sir Michael Stoute | 13-1-5 | -2.00 | -0.07 |
| William Haggas | 9-1-2 | -1.50 | -2.31 |
| Charles Hills | 6-1-2 | +28.00 | +18.63 |
| Michael Bell | 6-1-2 | +15.00 | +9.06 |
| David Menuisier | 4-1-1 | -1.00 | -1.80 |
| David O'Meara | 3-1-1 | +23.00 | +13.63 |
| John & Thady Gosden | 3-1-1 | +4.00 | +1.75 |
| Charlie & Mark Johnston | 2-1-1 | +13.00 | +7.75 |
| George Scott | 2-1-1 | +4.50 | +2.44 |
| J P Murtagh | 1-1-1 | +7.00 | +4.38 |
Chesterfield Cup Handicap Jockey Statistics
The leading jockey in the Chesterfield Cup Handicap over the last 20 renewals is William Buick, who has won the race twice, with those two winners coming from Migration (2021) and Al Aali (2026).
Here are some of the top Chesterfield Cup Handicap jockey statistics over the last 20 renewals (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):
| Jockey | R-W-P | Win | EW |
|---|---|---|---|
| William Buick | 12-2-4 | -2.50 | -2.36 |
| Ryan Moore | 14-1-5 | -3.00 | +0.05 |
| Silvestre De Sousa | 11-1-6 | -5.00 | +4.07 |
| Jamie Spencer | 10-1-2 | +24.00 | +13.13 |
| Jim Crowley | 9-1-3 | -1.50 | -1.69 |
| Daniel Tudhope | 6-1-4 | +20.00 | +15.27 |
| Dale Swift | 1-1-1 | +12.00 | +7.50 |
| Ben Coen | 1-1-1 | +7.00 | +4.38 |
| Billy Loughnane | 1-1-1 | +6.00 | +3.75 |
| James Doyle | 9-0-3 | -9.00 | -4.62 |
2027 Chesterfield Cup Handicap Trends
Favourites finishing positions (oldest to latest): 5, 7, 2, 5, 2, 9, (8, 10), 9, (1, 7), (1, 3, 4, 9, 14), 7, 1, (3, 9), 1, 1, 11, 7, 2, 6, (1, 5)
The percentage shown is the proportion of runners who fell under that factor. High percentages are less appealing than lower ones, as you would expect them to do well.
- 20 / 20 (77%) - No older than a 5yo
- 20 / 20 (79%) - Achieved a TS of 52+ (LTO)
- 20 / 20 (81%) - Within the first 13 of the market
- 20 / 20 (85%) - Not on HY/SFT/FM/STD-SLW/STD (LTO)
- 20 / 20 (86%) - Beaten no more -14½l (LTO)
- 20 / 20 (86%) - Achieved an RPR of 95+ (Last 3)
- 20 / 20 (86%) - Achieved a TS of 67+ (Season)
- 20 / 20 (87%) - In a field of 5 - 15 (Last Win)
- 20 / 20 (88%) - Carried 123 - 140lbs (LTO)
- 20 / 20 (88%) - Furthest Placed 1m½f - 1m5½f
- 19 / 20 (88%) - No bigger than 25/1 (LTO)
- 18 / 20 (74%) - No bigger than 20/1
- 18 / 20 (82%) - Achieved an RPR of 98+ (Last 5)
- 18 / 20 (84%) - Placed within last 4 starts
- 18 / 20 (87%) - Achieved an RPR of 94+ (Last Win)
Remember to use the trends listed above, along with the Goodwood racing predictions, to see if you can find the winner of the Chesterfield Cup Handicap. Did you know that we have an OLBG Betting School section on OLBG? It is a place to help you improve your betting experience with articles covering numerous topics.
Are you already a member? If not, then why not? With over £6,000 given away each month in the tipster competition, why not get involved? Remember, it is completely FREE! So, head over to the registration page to sign up today! If you are already a member, then share your thoughts on the Chesterfield Cup Handicap by adding a tip on the race here.
101 Ways to find Winners in Horse Racing
2027 Chesterfield Cup Handicap Runners & Shortlist
The runners and the final trends shortlist for the 2027 renewal of the Chesterfield Cup Handicap will be added once the final declarations are confirmed, which are usually 48 hours before the race.
Chesterfield Cup Handicap Trend Analysis
✅ The trend factor, which has produced 10+ winners and shows the best LSP, an LSP of +49.50, is when runners had 1 career win in the class.
❌ The worst-performing factor that has failed to produce a single winner is when runners ran in a race worth £3k on debut; when backing these, the trend shows a record of 0-74.
Here are the most recent winning draws, along with the further placings in brackets:
- 2026: Winner in 3 (8,11,18) [17 Runners]
- 2025: Winner in 8 (11,17,7) [18 Runners]
- 2024: Winner in 18 (13,12,11) [17 Runners]
- 2023: Winner in 16 (1,14) [15 Runners]
- 2022: Winner in 16 (2,9,6) [18 Runners]
The course which has produced the most winners of the Chesterfield Cup Handicap is York; there have been a total of 6 winners of this race who ran at York last time out. The next best course, which has produced the second most winners, is Newmarket (July); there have been a total of 3 winners of this race who ran at Newmarket (July) last time out.
The race is open to both sexes, with male runners having produced a total of 20 winners from a total of 319 runners, while female runners have produced 0 winners from a total of 7 runners.
Looking over the past renewals, there is only one stallion whose offspring have produced multiple winners of the Chesterfield Cup Handicap; that stallion, Rock Of Gibraltar, has produced 2 winners (2014,2011).
These are the stallions whose offspring have not produced a winner of the Chesterfield Cup Handicap despite multiple attempts:
- Dansili (0 Wins from 11 runners)
- Kingman (0 Wins from 9 runners)
- Galileo (0 Wins from 8 runners)
- Mastercraftsman (0 Wins from 8 runners)
- Sea The Stars (0 Wins from 7 runners)
Looking at the winning odds over the last 20 renewals, the biggest-priced winner was Ancient Rome in 2023, winning for Charles Hills at odds of 33/1 under the guidance of Jamie Spencer. Looking at the runners at the head of the market over the last 20 renewals, there have been 6 winning favourites in the race. Remember to use the best racing tipsters along with the information on this page to find a bet on the 2027 Chesterfield Cup Handicap.
Route to the Chesterfield Cup Handicap
Many trainers target races as preparation for the Chesterfield Cup Handicap. These are the races which the recent winners ran in before coming here:
| Info | Last Race |
|---|---|
| 2026 - Al Aali Newmarket (July) - 1st of 6 (3/1) | National Stud Handicap |
| 2025 - Westridge Windsor - 2nd of 9 (5/4) | Michael Foster Memorial Handicap |
| 2024 - Take Heart York - 8th of 20 (16/1) | John Smith's Cup |
| 2023 - Ancient Rome Chantilly - 3rd of 4 (4/1) | Prix Messidor |
| 2022 - Forest Falcon York - 14th of 22 (29/1) | John Smith's Cup |
| 2021 - Migration Salisbury - 4th of 12 (4/1) | Showcasing Standing At Whitsbury Manor Handicap |
| 2020 - Maydanny Newmarket (July) - 5th of 6 (4/6) | Each Way Extra At bet365 Handicap |
| 2019 - Fayez Ripon - 3rd of 9 (3/1) | Ripon Bell-Ringer Handicap |
| 2018 - Alfarris Sandown - 2nd of 8 (7/2) | Besso Handicap |
| 2017 - Fabricate Haydock - 6th of 16 (16/1) | Old Newton Cup |
Races Covered at Glorious Goodwood
Here is the schedule for the five-day Glorious Goodwood festival for races which we cover with blogs. Each race will be linked to the race blog, and details of last year's winner are in the table below.
Tuesday at Glorious Goodwood
Part of the British Champion Series, the Goodwood Cup is the highlight on the opening day, a marathon over two miles where stamina is key.
| Race | Last Winner | Info |
|---|---|---|
| Chesterfield Cup Handicap | Al Aali (FR) 4yo - 11/2 | George Scott William Buick |
| Vintage Stakes | Dr Rascal (GB) 2yo - 13/2 | Oliver Cole Kaiya Fraser |
| Lennox Stakes | Lake Forest (GB) 5yo - 10/11 | William Haggas Cieren Fallon |
| Goodwood Cup | Scandinavia (USA) 4yo - 6/5 | A P O'Brien Ryan Moore |
Wednesday at Glorious Goodwood
Run over a mile, the Sussex Stakes is the main race on the second day; this Group 1 is also part of the British Champion Series.
| Race | Last Winner | Info |
|---|---|---|
| Glorious Goodwood 1m4f Handicap | Infraad (IRE) 3yo - 2/1 | William Haggas Tom Marquand |
| Alice Keppel Fillies Conditions Stakes | Wild Blossom (IRE) 2yo - 5/4 | K R Burke James Doyle |
| Oak Tree Stakes | Flora Of Bermuda (IRE) 5yo - 5/2 | Andrew Balding James Doyle |
| Molecomb Stakes | Pershaada (IRE) 2yo - 11/4 | Richard Hannon Sean Levey |
| Sussex Stakes | Bow Echo (IRE) 3yo - 10/11 | George Boughey Billy Loughnane |
Thursday at Glorious Goodwood
The Group 1 Nassau Stakes is the highlight on Thursday, contested over 1m2f and restricted to only fillies and mares, the race is part of the British Champion Series.
| Race | Last Winner | Info |
|---|---|---|
| Kincsem Handicap | Ciarrai Abu (IRE) 3yo - 100/30 | Harry Eustace George Wood |
| Richmond Stakes | Mans Best Friend (IRE) 2yo - 11/2 | A P O'Brien Ryan Moore |
| Gordon Stakes | Enceladus (IRE) 3yo - 6/4 | Joseph Patrick O'Brien Dylan Browne McMonagle |
| Nassau Stakes | Diamond Necklace (IRE) 3yo - 4/6 | A P O'Brien Ryan Moore |
Friday at Glorious Goodwood
Friday features a couple of decent handicaps, with the Goodwood Handicap a stamina-testing race and the Golden Mile, which is a heritage handicap. The highlight of the day is the King George Stakes, a sprint run over five furlongs.
| Race | Last Winner | Info |
|---|---|---|
| Goodwood Handicap | Defiantly (FR) 4yo - 11/4 | Joseph Patrick O'Brien Dylan Browne McMonagle |
| Thoroughbred Stakes | Shayem (IRE) 3yo - 17/2 | K R Burke Clifford Lee |
| Golden Mile Handicap | Archivist (GB) 4yo - 16/1 | Hamad Al Jehani Callum Rodriguez |
| King George Stakes | American Affair (GB) 6yo - 12/1 | Jim Goldie Paul Mulrennan |
Saturday at Glorious Goodwood
Saturday is the day of one of the biggest handicaps on the flat, the Stewards Cup, 20+ runners over six furlongs compete in this heritage handicap.
| Race | Last Winner | Info |
|---|---|---|
| Summer Handicap | Hopewell Rock (IRE) 4yo - 5/1 | George Boughey Ryan Moore |
| Glorious Stakes | Enfjaar (IRE) 6yo - 8/1 | Roger Varian Ray Dawson |
| Lillie Langtry Stakes | Goodie Two Shoes (IRE) 7yo - 8/1 | Joseph Patrick O'Brien Dylan Browne McMonagle |
| Stewards Cup | Evening Saigon (IRE) 4yo - 16/1 | Hamad Al Jehani James Doyle |
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 Chesterfield Cup Handicap 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
Expert Guide
Andy Powell
Expert Guide
Other Principal Races at Goodwood Racecourse
Here are some other notable races at the Goodwood racecourse throughout the racing season that you may be interested in.
