Private purchase Tobys Heart made her first start for Gary Barber a winning one, taking the Limestone Turf Sprint at Keeneland. In her 3yo season, Tobys Heart would go on to take the Music City Stakes at Kentucky Downs after finishing 3rd in the G3 Lake George.
At 4, Tobys Heart ran 3rd in the G2 Monrovia at Santa Anita before taking the Unbridled Sidney Stakes at Churchill Downs during Kentucky Derby week. She was sold for $450,000 at the 2022 Keeneland November Sale.