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Cheltenham Hosts Legends Event to Celebrate 100 Years of Gold Cup Winners

Among the attendees was Simon Sherwood, known for his partnership with the legendary grey horse, Desert Orchid, clinching a memorable victory on March 16th, 1989.

Cheltenham Hosts Legends Event to Celebrate 100 Years of Cheltenham Gold Cup Winners
Cheltenham Hosts Legends Event to Celebrate 100 Years of Cheltenham Gold Cup Winners

Cheltenham Racecourse hosted illustrious figures from the world of Jump racing to mark the 100th anniversary of the Boodles Cheltenham Gold Cup, celebrating the achievements of its 100 winners.

The modern incarnation of the Cheltenham Gold Cup, initially a three-mile Flat race in the 1800s, owes its prestige to Frederick Cathcart, who served as the Clerk of the Course and Chairman of Cheltenham Racecourse from 1908 to 1934.

The first Cheltenham Gold Cup in 1924 was won by Red Splash, who received a splendid trophy made from 644 grams of nine-carat gold, coated with 18-carat gold for a lustrous finish.

In honour of the Gold Cup's centennial, a special Legends Lunch was held for all the living Gold Cup-winning trainers and jockeys at Cheltenham Racecourse on the day before the 2024 Festival (Monday, 11th March).

Among the attendees was Simon Sherwood, known for his partnership with the legendary grey horse, Desert Orchid, clinching a memorable victory on March 16th, 1989.

Sherwood reminisced, โ€œCheltenham holds a unique charm. The moment the gates to the winnerโ€™s enclosure open, it's unforgettable. The crowd parting as you return is always a highlight. The year Desert Orchid won was extraordinary, especially with the unexpected rain, making it a day to remember.

"Cheltenham is the pinnacle, the ultimate goal at the season's start. By December, you have a sense of which horses are contenders.

"Desert Orchid had already secured a Whitbread Gold Cup victory by the time of the Gold Cup, ensuring his stamina. The challenge was Cheltenham's left-handed track.

"I was confident that if we were close to the lead at the last jump, Desert Orchid would have the determination to ascend the hill.

"Crossing the last hurdle, I gave it my all, aware such an opportunity might never come again. The crowd's energy and the victory were unparalleled, made even more special by the presence of the Queen Mother. It was an extraordinary day filled with cherished memories."

Despite the high of such achievements, Sherwood chose to retire at the close of the 1988-89 season, a decision he had contemplated beforehand.

He elaborated, โ€œI had experienced considerable success and felt I had accomplished my goals.

"Being in good health and at 31, I decided it was time to retire. The realization that I wouldn't ride Dessie again was hard, but changing my mind seemed riskier, often leading to injuries.

"The only moment of regret was missing Desert Orchid's win at the Irish Grand National in 1990. Participating in that would have been incredible.โ€

All Cheltenham Gold Cup Winners

DateWinnerStarting PriceJockeyOwner
1924, 12 MarchRed Splash5/1Dick ReesMaj. Humphrey Wyndham
1925, 11 MarchBallinode3/1Ted LeaderChristopher Bentley
1926, 9 MarchKoko10/1Tim HameyFrank Barbour
1927, 8 MarchThrown In10/1Mr Hugh Grosvenor2nd Lord Stalbridge
1928, 13 MarchPatron Saint7/2Dick ReesF. W. Keen
1929, 12 MarchEaster Hero7/4FDick ReesJohn Hay Whitney
1930, 11 MarchEaster Hero8/11FTommy CullinanJohn Hay Whitney
No race 1931 
1932, 1 MarchGolden Miller13/2Ted LeaderDorothy Paget
1933, 7 MarchGolden Miller4/7FBilly StottDorothy Paget
1934, 6 MarchGolden Miller6/5FGerry WilsonDorothy Paget
1935, 14 MarchGolden Miller1/2FGerry WilsonDorothy Paget
1936, 12 MarchGolden Miller21/20FEvan WilliamsDorothy Paget
No race 1937 
1938, 10 MarchMorse Code13/2Danny MorganDealtry C. Part
1939, 9 MarchBrendan's Cottage8/1George OwenJean Smith-Bingham
1940, 20 MarchRoman HackleEvensFEvan WilliamsDorothy Paget
1941, 20 MarchPoet Prince7/2Roger BurfordDavid Sherbrooke
1942, 21 MarchMedoc II9/2Frenchie Nicholson7th Earl of Sefton
Races not held in 1943โ€“44 due to World War II 
1945, 17 MarchRed Rower11/4FDavy Jones2nd Lord Stalbridge
1946, 14 MarchPrince Regent4/7FTim HydeJimmy Rank
1947, 12 AprilFortina8/1Mr Richard Black3rd Baron Grimthorpe
1948, 4 MarchCottage Rake10/1Aubrey BrabazonFrank Vickerman
1949, 11 AprilCottage Rake4/6FAubrey BrabazonFrank Vickerman
1950, 9 MarchCottage Rake5/6FAubrey BrabazonFrank L. Vickerman
1951, 25 AprilSilver Fame6/4FMartin Molony1st Baron Bicester
1952, 6 MarchMont Tremblant8/1Dave DickDorothy Paget
1953, 5 MarchKnock Hard11/2Tim MolonyMoya Keogh
1954Four Ten100/6Tommy CusackAlan Strange
1955Gay Donald33/1Tony GranthamPhilip Burt
1956Limber Hill11/8FJimmy PowerJames Davey
1957Linwell100/9Michael ScudamoreDavid Brown
1958Kerstin7/1Stan HayhurstGeorge H. Moore
1959Roddy Owen5/1Bobby Beasley12th Earl of Fingall
1960Pas Seul6/1Bill ReesJohn Rogerson
1961Saffron Tartan2/1Fred WinterGuy Westmacott
1962Mandarin7/2Fred WinterPeggy Hennessy
1963Mill House7/2Willie RobinsonBill Gollings
1964Arkle7/4Pat TaaffeDuchess of Westminster
1965Arkle30/100FPat TaaffeDuchess of Westminster
1966Arkle1/10FPat TaaffeDuchess of Westminster
1967Woodland Venture100/8Terry BiddlecombeHarry Collins
1968Fort Leney11/2Pat TaaffeJohn Thomson
1969What A Myth8/1Paul KellewayLady Lucy Weir
1970L'Escargot33/1Tommy CarberryRaymond R. Guest
1971L'Escargot7/2Tommy CarberryRaymond R. Guest
1972Glencaraig Lady6/1Frank BerryPatrick Doyle
1973The Dikler9/1Ron BarryPeggy August
1974Captain Christy7/1Bobby BeasleyJane Samuel
1975Ten Up2/1Tommy CarberryDuchess of Westminster
1976Royal Frolic14/1John BurkeSir Edward Hanmer
1977Davy Lad14/1Dessie HughesAnne-Marie McGowan
1978Midnight Court5/2John FrancomeOlive Jackson
1979Alverton5/1Jonjo O'NeillSnailwell Stud Co.
1980Master Smudge 14/1Richard HoareArthur Barrow
1981Little Owl6/1Mr Jim WilsonRobin & Jim Wilson
1982Silver Buck8/1Robert EarnshawChristine Feather
1983Bregawn100/30Graham BradleyJames Kennelly
1984Burrough Hill Lad7/2Phil TuckStan Riley
1985Forgive 'n Forget7/1Mark DwyerTim Kilroe & Sons Ltd
1986Dawn Run15/8fJonjo O'NeillCharmian Hill
1987The Thinker13/2Ridley LambTom McDonagh
1988Charter Party10/1Richard DunwoodySmith / Mould
1989Desert Orchid5/2Simon SherwoodRichard Burridge
1990Norton's Coin100/1Graham McCourtSirrel Griffiths
1991Garrison Savannah16/1Mark PitmanAutofour Engineering
1992Cool Ground25/1Adrian MaguireWhitcombe Manor Racing
1993Jodami8/1Mark DwyerJohn Yeadon
1994The Fellow7/1Adam KondratMarquesa de Moratalla
1995Master Oats100/30Norman WilliamsonPaul Matthews
1996Imperial Call9/2Conor O'DwyerLisselan Farms Ltd
1997Mr Mulligan20/1Tony McCoyM. & G. Worcester
1998Cool Dawn25/1Andrew ThorntonDido Harding
1999See More Business16/1Mick FitzgeraldPaul Barber / Keighley
2000Looks Like Trouble9/2Richard JohnsonTim Collins
No race 2001 
2002Best Mate7/1Jim CullotyJim Lewis
2003Best Mate13/8FJim CullotyJim Lewis
2004Best Mate8/11FJim CullotyJim Lewis
2005Kicking King4/1FBarry GeraghtyConor Clarkson
2006War of Attrition15/2Conor O'DwyerGigginstown House Stud
2007Kauto Star5/4FRuby WalshClive D. Smith
2008Denman9/4Sam ThomasPaul Barber / Findlay
2009Kauto Star7/4FRuby WalshClive D. Smith
2010Imperial Commander7/1Paddy BrennanOur Friends in the North
2011Long Run7/2FMr Sam Waley-CohenRobert Waley-Cohen
2012Synchronised8/1Tony McCoyJ. P. McManus
2013Bobs Worth11/4FBarry GeraghtyThe Not Afraid Partnership
2014Lord Windermere20/1Davy RussellDr. Ronan Lambe
2015Coneygree7/1Nico de BoinvilleThe Max Partnership
2016Don Cossack9/4FBryan CooperGigginstown House Stud
2017Sizing John7/1Robbie PowerAnn & Alan Potts
2018Native River5/1Richard JohnsonBrocade Racing
2019Al Boum Photo12/1Paul TownendMrs J Donnelly
2020Al Boum Photo100/30FPaul TownendMrs J Donnelly
2021Minella Indo9/1Jack KennedyBarry Maloney
2022A Plus Tard3/1FRachael BlackmoreCheveley Park Stud
2023Galopin Des Champs7/5FPaul TownendMrs Audrey Turley

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