Ussery's best finish in the Belmont Stakes was in 1959 aboard the colt, Bagdad. In 1960 he won the Hopeful Stakes aboard that year's Eclipse Award 2-year-old champion, Hail To Reason. That same year he rode Bally Ache to victory in the Florida Derby and the Flamingo Stakes en route to a second place finish in the Kentucky Derby and then a win in the Preakness Stakes. In 1967 Ussery won the Kentucky Derby on Proud Clarion and won it again in 1968 aboard Dancer's Image. However, after phenylbutazone, a substance banned in Kentucky at that time but later sanctioned after it was proven not to affect a horse's performance, was found in Dancer's Image's post-race urine test, Dancer's Image was listed as having finished last.
Bobby Ussery retired in 1974 having won 3,611 races. In 1980, he was inducted into the National Museum of Racing and Hall of Fame.