As a two-year-old, she won the Miss Grillo Stakes and finished second in the Breeders' Cup Juvenile Fillies Turf.

Winter Memories has been ridden by Jose Lezcano until she lost in the Lake Placid Stakes when he was replaced with Javier Castellano.

On October 3, 2010, Winter Memories won the 1 1/16 miles Miss Grillo Stakes by 5 lengths at Belmont Park.

On November 5, 2010, Winter Memories finished 2nd in Breeders' Cup Juvenile Fillies Turf as a favorite to More Than Real.

[citation needed] Winter Memories won her first grade 1 in the Garden City Stakes at Belmont Park.

On July 28, 2012 Winter Memories took her second grade I in the Diana Stakes accelerating at the final bend for a length and half victory.

[1] In October 2023, Darby Dan Farm owner John Phillips confirmed that Winter Memories was euthanized earlier that year–on May 16–due to issues with her hind suspensory ligaments that made it difficult for her to stand.