Swiss Skydiver

Swiss Skydiver's first race was on November 16 at Churchill Downs, which she won. She returned less than two weeks later on November 20 to finish second in an Allowance Optional Claiming race.

Swiss Skydiver started off the 2020 season on January 18 with a 5th-place finish in the Gasparilla Stakes.[9] She then came in 3rd in 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 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 so far.

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.

Swiss Skydiver's biggest win of her career was the 2020 Preakness Stakes, the second leg of the Triple Crown, where she was the first filly win the race since Rachel Alexandra in 2009. 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, in one of the most thrilling stretch duels in the history of the Triple Crown. Swiss Skydiver refused to let Authentic past her and she won by a neck.[15] The third-place finisher, Jesus' Team, was 9+3⁄4 behind Authentic.[16] Swiss Skydiver's time of 1:53.28 was the second-fastest in Preakness history, behind only Secretariat's 1:53.00 in 1973.[17] She is only the ninth horse to ever break 1:54 in the 99 years that the Preakness has been run at 1+3⁄16 miles.

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.[18]

In January, the Eclipse Awards named Swiss Skydiver American Champion Three-Year-Old Filly of 2020. Bloodhorse.com later said she "soar[ed] to Champion 3-Year-Old Filly Title."

Swiss Skydiver ran her first race as a four-year-old in the Beholder Mile Stakes at Santa Anita Park. She broke fourth, and the leader Golden Principal who ran fractions of 23:14, 46.80 and 1:11.19. In the stretch, Swiss Skydiver took the lead and easily won with 2+3⁄4 lengths in a time of 1:36.18. The win was even more impressive because Swiss Skydiver had to ship out to California to face a strong field at 1/4 of a mile less than her ideal distance.

After that easy win, she was shipped to Oaklawn Park for a re-match with Monomoy Girl in the Apple Blossom Handicap at 1 1/16 miles. Everyone was firmly convinced that this would be a match race between Monomoy Girl and Swiss Skydiver. The third favorite, Letruska, immediately took the lead, while Swiss Skydiver ran on the railing and Monomoy Girl ran three wide. Letruska set fractions of 23.43, 47.96 and 1: 12.26. Robby Albarado let Swiss Skydiver run on the inside, just like she did in the Preakness Stakes. Next to her was Letruska and on the outside was Monomoy Girl. Monomoy Girl took the lead while Swiss Skydiver didn't fire. In the end, Letruska would come back and defeat Monomoy Girl with a short nose while Swiss Skydiver would finish 6+1⁄2 lengths behind Letruska and Monomoy Girl.

Swiss Skydiver was going to make her next start in the Shuvee Stakes at Saratoga Racecourse on July 25, but a two-year-old filly in her barn tested positive for Equine Herpesvirus-1 and the barn was quarantined and none of the horses allowed to race until August 1.

Swiss Skydiver's next race was the Grade 1 Whitney Stakes against older males at Saratoga Racecourse on August 7. About the Whitney, trainer Kenny McPeek said "fillies have won this race before. It's not my first choice, but I don't have any control over the fact that they're not going to let me run in the Shuvee. My preference would be to have an easier race first time back, but the powers that be said that's not going to, timing-wise, going to work. But she's capable of beating some of these horses. Is it ambitious? Yes. But so was the Preakness, so..." Swiss Skydiver also hasn't lost two races in a row for nearly eighteen months. Swiss Skydiver struggled to keep up with the front running Knicks Go and finished fourth beaten by over 10 lengths.[19]