[1] Born in Enfield, Middlesex in South East England, Bailie grew up on a farm where she learned to ride horses.
In 1970, she went out on her own and in 1977 became the first woman trainer in American racing history to win a $100,000 when her horse Tequillo Boogie captured the New York Breeders' Futurity at Finger Lakes Race Track in Farmington, New York.
In 1982, she became the first woman trainer to win a $200,000 race when she conditioned the winner of the Pegasus Handicap at Meadowlands Racetrack in East Rutherford, New Jersey.
[2] At a 1982 Fasig-Tipton dispersal auction in Saratoga, Sally Bailie paid $8,000 for a two-year-old grandson of Northern Dancer named Win.
Sally Bailie died of cancer, aged 58, at Winthrop-University Hospital in Mineola, New York, on Long Island.