Swiss Skydiver

Swiss Skydiver's first race was on November 16, 2019, at Churchill Downs, where she came in first. She returned less than two weeks later on November 20, 2019, coming in second place in an Allowance Optional Claiming race.

Swiss Skydiver started off the 2020 season on January 18 with a 5th-place finish at the Gasparilla Stakes.[9] She then came in 3rd at the Rachel Alexandra Stakes on February 15.[10] She got her first graded stakes win on March 28, when she won the Gulfstream Oaks. She came in at 9:1 odds and led the race before beating Lucrezia by ​3 ¹⁄₂ lengths.[11] She then earned her second graded stakes win on May 1, when she won the Fantasy Stakes. She came in as the underdog at 16:1 odds and defeated Venetian Harbor by ​2 ¹⁄₂ lengths.[12]

Swiss Skydiver captured her third graded stakes win when she won the Santa Anita Oaks on June 6.[13] She defeated Meneith by four lengths as the 3:5 favorite. On July 11, she competed in her first race against male horses at the Blue Grass Stakes. She came in as the 2:1 favorite but was defeated by Art Collector by ​3 ¹⁄₂ lengths.[14]

She came back to win the 2020 Alabama Stakes, the third leg of the New York Triple Tiara, by 3 1/2 lengths, establishing her as the top three-year-old filly of 2020.

In the 2020 Kentucky Oaks, Swiss Skydiver ran in third place for most of the race, before passing the tiring favorite Gamine and just falling short of the eventual winner Shedaresthedevil.

Her next start and biggest win of her career was the 2020 Preakness Stakes, where she was the first filly to enter the Preakness since Ria Antonia in 2014. Swiss Skydiver took the lead on the final turn and battled 2020 Kentucky Derby winner Authentic down the stretch, both well ahead of the rest of the field. She won by a neck, the first filly to win the Preakness since Rachel Alexandra in 2009.[15] The third-place finisher, Jesus’ Team, was ​9 ³⁄₄ behind Authentic.[16]

Swiss Skydiver moved up to second in the NTRA Top Three-Year-Old Poll, and ninth in the NTRA Top Thoroughbred Poll.

Her next start could have been either the 2 million Breeders' Cup Distaff against her own gender and the champion mare Monomoy Girl, or the 6 million Breeders' Cup Classic against older males, where she would have a shot at Horse of the Year if she won. She had qualified for both races, the Alabama Stakes for the Distaff and the Preakness Stakes for the Classic. Her owner Peter Callahan was strongly leaning towards the Distaff, but trainer Kenny McPeek was keen to take a shot at the Classic.

Swiss Skydiver's connections chose the Breeders' Cup Distaff. But she stumbled badly coming out of the gate and her race was over before it even began. She moved into contention at the top of the homestretch before tiring to seventh place. Her stumble out of the gate left her no chance to win, but her connections hoped for a possible rematch with the winner Monomoy Girl in 2021.

For her thrilling Preakness Stakes win and coast to coast victories at nine different tracks, Swiss Skydiver was a nominee for the 2020 Secretariat Vox Populi Award.

In the 2020 World's Best Racehorse Rankings, Swiss Skydiver was rated on 122, making her the equal twenty-first best racehorse in the world and the best three-year-old filly alongside Love and Gamine.[17]

Swiss Skydiver is expected to continue racing in 2021 as a four-year-old.