6 minutes 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 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, “Cheltenham holds a unique charm. The moment the gates to the winner’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, “I 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.”
All Cheltenham Gold Cup Winners
| Date | Winner | Starting Price | Jockey | Owner |
|---|---|---|---|---|
| 1924, 12 March | Red Splash | 5/1 | Dick Rees | Maj. Humphrey Wyndham |
| 1925, 11 March | Ballinode | 3/1 | Ted Leader | Christopher Bentley |
| 1926, 9 March | Koko | 10/1 | Tim Hamey | Frank Barbour |
| 1927, 8 March | Thrown In | 10/1 | Mr Hugh Grosvenor | 2nd Lord Stalbridge |
| 1928, 13 March | Patron Saint | 7/2 | Dick Rees | F. W. Keen |
| 1929, 12 March | Easter Hero | 7/4F | Dick Rees | John Hay Whitney |
| 1930, 11 March | Easter Hero | 8/11F | Tommy Cullinan | John Hay Whitney |
| No race 1931 | ||||
| 1932, 1 March | Golden Miller | 13/2 | Ted Leader | Dorothy Paget |
| 1933, 7 March | Golden Miller | 4/7F | Billy Stott | Dorothy Paget |
| 1934, 6 March | Golden Miller | 6/5F | Gerry Wilson | Dorothy Paget |
| 1935, 14 March | Golden Miller | 1/2F | Gerry Wilson | Dorothy Paget |
| 1936, 12 March | Golden Miller | 21/20F | Evan Williams | Dorothy Paget |
| No race 1937 | ||||
| 1938, 10 March | Morse Code | 13/2 | Danny Morgan | Dealtry C. Part |
| 1939, 9 March | Brendan's Cottage | 8/1 | George Owen | Jean Smith-Bingham |
| 1940, 20 March | Roman Hackle | EvensF | Evan Williams | Dorothy Paget |
| 1941, 20 March | Poet Prince | 7/2 | Roger Burford | David Sherbrooke |
| 1942, 21 March | Medoc II | 9/2 | Frenchie Nicholson | 7th Earl of Sefton |
| Races not held in 1943–44 due to World War II | ||||
| 1945, 17 March | Red Rower | 11/4F | Davy Jones | 2nd Lord Stalbridge |
| 1946, 14 March | Prince Regent | 4/7F | Tim Hyde | Jimmy Rank |
| 1947, 12 April | Fortina | 8/1 | Mr Richard Black | 3rd Baron Grimthorpe |
| 1948, 4 March | Cottage Rake | 10/1 | Aubrey Brabazon | Frank Vickerman |
| 1949, 11 April | Cottage Rake | 4/6F | Aubrey Brabazon | Frank Vickerman |
| 1950, 9 March | Cottage Rake | 5/6F | Aubrey Brabazon | Frank L. Vickerman |
| 1951, 25 April | Silver Fame | 6/4F | Martin Molony | 1st Baron Bicester |
| 1952, 6 March | Mont Tremblant | 8/1 | Dave Dick | Dorothy Paget |
| 1953, 5 March | Knock Hard | 11/2 | Tim Molony | Moya Keogh |
| 1954 | Four Ten | 100/6 | Tommy Cusack | Alan Strange |
| 1955 | Gay Donald | 33/1 | Tony Grantham | Philip Burt |
| 1956 | Limber Hill | 11/8F | Jimmy Power | James Davey |
| 1957 | Linwell | 100/9 | Michael Scudamore | David Brown |
| 1958 | Kerstin | 7/1 | Stan Hayhurst | George H. Moore |
| 1959 | Roddy Owen | 5/1 | Bobby Beasley | 12th Earl of Fingall |
| 1960 | Pas Seul | 6/1 | Bill Rees | John Rogerson |
| 1961 | Saffron Tartan | 2/1 | Fred Winter | Guy Westmacott |
| 1962 | Mandarin | 7/2 | Fred Winter | Peggy Hennessy |
| 1963 | Mill House | 7/2 | Willie Robinson | Bill Gollings |
| 1964 | Arkle | 7/4 | Pat Taaffe | Duchess of Westminster |
| 1965 | Arkle | 30/100F | Pat Taaffe | Duchess of Westminster |
| 1966 | Arkle | 1/10F | Pat Taaffe | Duchess of Westminster |
| 1967 | Woodland Venture | 100/8 | Terry Biddlecombe | Harry Collins |
| 1968 | Fort Leney | 11/2 | Pat Taaffe | John Thomson |
| 1969 | What A Myth | 8/1 | Paul Kelleway | Lady Lucy Weir |
| 1970 | L'Escargot | 33/1 | Tommy Carberry | Raymond R. Guest |
| 1971 | L'Escargot | 7/2 | Tommy Carberry | Raymond R. Guest |
| 1972 | Glencaraig Lady | 6/1 | Frank Berry | Patrick Doyle |
| 1973 | The Dikler | 9/1 | Ron Barry | Peggy August |
| 1974 | Captain Christy | 7/1 | Bobby Beasley | Jane Samuel |
| 1975 | Ten Up | 2/1 | Tommy Carberry | Duchess of Westminster |
| 1976 | Royal Frolic | 14/1 | John Burke | Sir Edward Hanmer |
| 1977 | Davy Lad | 14/1 | Dessie Hughes | Anne-Marie McGowan |
| 1978 | Midnight Court | 5/2 | John Francome | Olive Jackson |
| 1979 | Alverton | 5/1 | Jonjo O'Neill | Snailwell Stud Co. |
| 1980 | Master Smudge | 14/1 | Richard Hoare | Arthur Barrow |
| 1981 | Little Owl | 6/1 | Mr Jim Wilson | Robin & Jim Wilson |
| 1982 | Silver Buck | 8/1 | Robert Earnshaw | Christine Feather |
| 1983 | Bregawn | 100/30 | Graham Bradley | James Kennelly |
| 1984 | Burrough Hill Lad | 7/2 | Phil Tuck | Stan Riley |
| 1985 | Forgive 'n Forget | 7/1 | Mark Dwyer | Tim Kilroe & Sons Ltd |
| 1986 | Dawn Run | 15/8f | Jonjo O'Neill | Charmian Hill |
| 1987 | The Thinker | 13/2 | Ridley Lamb | Tom McDonagh |
| 1988 | Charter Party | 10/1 | Richard Dunwoody | Smith / Mould |
| 1989 | Desert Orchid | 5/2 | Simon Sherwood | Richard Burridge |
| 1990 | Norton's Coin | 100/1 | Graham McCourt | Sirrel Griffiths |
| 1991 | Garrison Savannah | 16/1 | Mark Pitman | Autofour Engineering |
| 1992 | Cool Ground | 25/1 | Adrian Maguire | Whitcombe Manor Racing |
| 1993 | Jodami | 8/1 | Mark Dwyer | John Yeadon |
| 1994 | The Fellow | 7/1 | Adam Kondrat | Marquesa de Moratalla |
| 1995 | Master Oats | 100/30 | Norman Williamson | Paul Matthews |
| 1996 | Imperial Call | 9/2 | Conor O'Dwyer | Lisselan Farms Ltd |
| 1997 | Mr Mulligan | 20/1 | Tony McCoy | M. & G. Worcester |
| 1998 | Cool Dawn | 25/1 | Andrew Thornton | Dido Harding |
| 1999 | See More Business | 16/1 | Mick Fitzgerald | Paul Barber / Keighley |
| 2000 | Looks Like Trouble | 9/2 | Richard Johnson | Tim Collins |
| No race 2001 | ||||
| 2002 | Best Mate | 7/1 | Jim Culloty | Jim Lewis |
| 2003 | Best Mate | 13/8F | Jim Culloty | Jim Lewis |
| 2004 | Best Mate | 8/11F | Jim Culloty | Jim Lewis |
| 2005 | Kicking King | 4/1F | Barry Geraghty | Conor Clarkson |
| 2006 | War of Attrition | 15/2 | Conor O'Dwyer | Gigginstown House Stud |
| 2007 | Kauto Star | 5/4F | Ruby Walsh | Clive D. Smith |
| 2008 | Denman | 9/4 | Sam Thomas | Paul Barber / Findlay |
| 2009 | Kauto Star | 7/4F | Ruby Walsh | Clive D. Smith |
| 2010 | Imperial Commander | 7/1 | Paddy Brennan | Our Friends in the North |
| 2011 | Long Run | 7/2F | Mr Sam Waley-Cohen | Robert Waley-Cohen |
| 2012 | Synchronised | 8/1 | Tony McCoy | J. P. McManus |
| 2013 | Bobs Worth | 11/4F | Barry Geraghty | The Not Afraid Partnership |
| 2014 | Lord Windermere | 20/1 | Davy Russell | Dr. Ronan Lambe |
| 2015 | Coneygree | 7/1 | Nico de Boinville | The Max Partnership |
| 2016 | Don Cossack | 9/4F | Bryan Cooper | Gigginstown House Stud |
| 2017 | Sizing John | 7/1 | Robbie Power | Ann & Alan Potts |
| 2018 | Native River | 5/1 | Richard Johnson | Brocade Racing |
| 2019 | Al Boum Photo | 12/1 | Paul Townend | Mrs J Donnelly |
| 2020 | Al Boum Photo | 100/30F | Paul Townend | Mrs J Donnelly |
| 2021 | Minella Indo | 9/1 | Jack Kennedy | Barry Maloney |
| 2022 | A Plus Tard | 3/1F | Rachael Blackmore | Cheveley Park Stud |
| 2023 | Galopin Des Champs | 7/5F | Paul Townend | Mrs Audrey Turley |
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