Simon Sherwood notched up seven Cheltenham Festival Winners between 1985 and 1989 recording a rare Champion Chase/Gold Cup Double in 1989 winning the latter race on the magnificent Desert Orchid.
The race was later voted best horse race ever by readers of the Racing Post. We have Simon and Dessie here:
In all Simon won nine of the ten races he rode on Desert Orchid. His Cheltenham Festival winners were :
| Race | Year | Horse | Trainer |
| Kim Muir | 1985 | Glyde Court | Fred Winter |
| Cathcart | 1986 | Half Free | Fred Winter |
| Neptune | 1987 | The West Awake | Oliver Sherwood |
| Neptune | 1988 | Rebel Song | Oliver Sherwood |
| RSA Chase | 1988 | The West Awake | Oliver Sherwood |
| Champion Chase | 1989 | Barnbrook Again | David Elsworth |
| Gold Cup | 1989 | Desert Orchid | David Elsworth |
