Purchased for $170,000 from the Fasig-Tipton October Yearling Sale in 2019, Goodnight Olive made her stakes debut a winning one, scoring in the G1 Ballerina, beating Champion Female Sprinter as well as fellow G1 winner Bella Sofia. Goodnight Olive capped a perfect 2022 season with a comprehensive win in the G1 Breeders’ Cup Filly & Mare Sprint, wrapping up divisional honors along the way.

Goodnight Olive continued her winning streak in her first start of 2023, taking the G1 Madison at Keeneland, marking her 3rd consecutive G1 win. After an unlucky 3rd place finish in the G1 Derby City Distaff, Goodnight Olive got back to her winning ways in the G2 Bed o’ Roses at Belmont Park in the spring of her 5yo season. After a 2nd place finish in the G1 Ballerina which saw her earn a 108 Beyer Speed Figure, she would cap off her 5yo season by taking the G1 Breeders’ Cup Filly & Mare Sprint for the second consecutive year. Three days later, she sold for $6,000,000 at Fast-Tipton’s November Night of the Stars to John Stewart.