Steeplechase:
Colonial Cup Steeplechase
(1975, 1977, 1979, 1983, 1984, 1985, 1986, 1988, 1989, 1991, 1992, 1999, 2000)
New York Turf Writers Cup Handicap
(1979, 1983, 1984, 1989, 1990, 1991, 1992, 1994,1997, 2000, 2001, 2006)
Royal Chase for the Sport of Kings Hurdle
(2002, 2007, 2008)
Flat racing:
Flower Bowl Invitational Stakes (1982, 1983)
Diana Handicap (1993, 2008, 2009)
Man o' War Stakes (2001, 2002)
Sword Dancer Invitational Handicap (2001, 2002)
United Nations Handicap (2002)
First Lady Stakes (2008)
Humana Distaff Handicap (2009)
Vinery Madison Stakes (2009)
Jenny Wiley Stakes (2009)
Chicago Handicap (2009)
Arlington Handicap (2009)
Northern Dancer Turf Stakes (2009)
Kentucky Cup Turf Stakes (2009)
Valedictory Stakes (2009)
Dixie Stakes (2014)
Jonathan E. Sheppard (born December 2, 1940 in Ashwell, Hertfordshire, England) is a Hall of Fame trainer in American Thoroughbred horse racing.
Sheppard came to the United States in 1961 and in 1966 won his first race with Haffaday in a steeplechase event at My Lady's Manor, Maryland. In 1973 he won his first earnings championship in steeplechase racing. He went on to win the earnings title another twenty-three times. He has trained the winner of four Breeders' Cup Grand National Steeplechase and holds the record for most wins in the Colonial Cup Steeplechase with eleven. Sheppard is the only trainer to win the American steeplechase Triple Crown, doing it with Flatterer, the only horse to win the Eclipse Award for Outstanding Steeplechase horse four years in a row.