On September 3, 2010, Winter Memories won her first start and defeated nine other opponents. She broke her maiden in a Maiden Special Weight going 1 1/16 miles at Saratoga. She was ridden by Jose Lezcano, carried 119 lbs and won by 1 1/2 lengths.
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.
Winter Memories went on to win the Grade 2 Lake George Stakes on the July 27, 2011. She broke slow and was last in the six horse field. She had been stopped, but than she went to the outside and won by 4 1/2 lengths.[citation needed]
Winter Memories won her first grade 1 in the Garden City Stakes at Belmont Park. Like her other races, she made a late charge, but she had to overcome major traffic issues to win in a time of 1:51.06. Her late charge was so strong that racetrack announcer Tom Durkin called her a "grey bullet".
2012 season
Winter Memories began her four-year-old campaign with a win in the Beaugay Stakes at Belmont Park in May but then disappointed in the Just A Game Stakes behind Tapitsfly. 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. The win saw her emulate her dam Memories of Silver, who won the race in 1998. After the race, her owner John Phillips described her as "a very, very good horse". During the home stretch of the Diana Stakes, however, Winter Memories jolted to the right and appeared to be injured. This spurred on extensive veterinary examinations in the days after the race. It was discovered that Winter Memories had been suffering form a degenerative bone disease for quite some time. On August 9, 2012, owner Phillips Racing Partnership and trainer James J. Toner announced her retirement from racing.[5]
Broodmare career
As a dam Winter Memories produced Winter Sunset, a filly who won black-type and listed stakes races at Fair Grounds Race Track and Horseshoe Indianapolis and placed in three Grade III races as a three-year-old,[6] and Seasons, who placed in four stakes races in his career.[7] Both horses were sired by three-time leading sireTapit.[1] Her last foal is a filly by Mendelssohn born in 2022.[1]
Death
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.[1]