With trainer Kenny McPeek declaring to send multiple Grade 1 winner Swiss Skydiver (by Daredevil) to the Preakness Stakes on Oct. 3, our memory turned to the last filly to win the classic against the colts: Horse of the Year Rachel Alexandra (Medaglia d’Oro) in 2009.

The striking dark bay wasn’t the only filly to win that classic, however. Although Rachel Alexandra is the only filly to win a classic in the 21st century, four other fillies had won the Preakness in the preceding century. Flocarline had been the first filly to win a Preakness in 1903, then Whimsical won the race in 1906, Rhine Maiden won in 1915 (the same year that Regret won the Kentucky Derby), and Nellie Morse won in 1924.

Whimsical — winner of the 1906 Preakness Stakes — was a daughter of the British stallion Orlando (by Orme) out of the Hindoo mare Kismet. Painting by Henry Stull.

Although it was 85 years after Nellie Morse until another filly won the Preakness, 10 more had tried the classic during the interim. The most famous of these had been the champions and Kentucky Derby winners Genuine Risk (Exclusive Native) in 1980 and Winning Colors (Caro) in 1988.

In 1980, the fetching chestnut Genuine Risk had become the second Kentucky Derby winner in three years for the Raise a Native stallion Exclusive Native. Neither Exclusive Native nor his sire had made any waves in the classics during their racing careers, but both had proven notably more capable of getting classic stock as sires.

Raise a Native sired 1969 Kentucky Derby and Preakness winner Majestic Prince, as well as Alydar, who finished second in each of the Triple Crown races behind Affirmed, the first classic winner by Exclusive Native.

Both Affirmed and Genuine Risk were scopy chestnuts with quality; their good looks made them noticeable on the racetrack and helped win thousands of fans for racing. Following her historic Derby success 65 years after Regret, Genuine Risk then finished second in a controversial Preakness when she was carried wide coming into the stretch by subsequent winner Codex (Arts and Letters). An objection lodged against the winner was not allowed.

Genuine Risk went to the Belmont Stakes, even without the Triple Crown as the historic attraction, but this time the beloved filly finished second to the mud-loving Temperence Hill (Stop the Music), who later was voted the champion 3-year-old colt.

No other filly previously had raced in each of the races of the Triple Crown, and Genuine Risk showed her high class and athletic ability as she finished in the money in each race. As a result, Genuine Risk ranks as one of the great race fillies of the past 50 years.

But just eight years later, another filly ran in each of the Triple Crown races.

A thrashing big filly, Winning Colors had brought $575,000 as a Keeneland July yearling, and the leggy daughter of the gray stallion Caro took some time to strengthen and fill out her big frame. After winning a pair of races at two, she advanced rapidly to top-class form in winning the Santa Anita Derby and then the Kentucky Derby. In the latter race, Winning Colors defeated the previous season’s top juvenile colt, Forty Niner (Mr. Prospector) by a neck, with Risen Star (Secretariat) in third.

Brought back by trainer D. Wayne Lukas for the Preakness and a possible tilt for the Triple Crown, Winning Colors was challenged early and aggressively by Forty Niner, and at the finish, Risen Star was the fast-closing winner, with Winning Colors in third.

Both classic winners came back for the Belmont Stakes, and Risen Star prevailed by 15 lengths in the fast time of 2:26 2/5, which at the time was the second-fastest Belmont ever run behind only his great sire’s 2:24. Since 1988, Easy Goer and A.P. Indy each have won the Belmont in 2:26.

Winning Colors had made the early pace, tried to stay with Risen Star when he was winding up his convincing impression of Secretariat, and finished unplaced in sixth. Winning Colors never won another top-level race, but the lovely gray did finish second in both the G1 Maskette and Breeders’ Cup Distaff to the unbeaten Personal Ensign (Private Account).

In the latter race, run under cold and wet conditions at Churchill Downs later in 1989, Winning Colors had taken the lead and controlled the race to such an extent that Personal Ensign appeared to have little chance of even hitting the board as the field came into the stretch. The imperturbable bay filly refused to give up, gained with every stride through the stretch, and won her 13th and final start in one of the most exciting and heroic efforts imaginable.

These fillies secured the status of supreme champions by overcoming adversity and capturing victory when the probability or circumstances didn’t favor them. If Swiss Skydiver can live up to these supreme examples of the race filly, she will make the Preakness one more great race to remember.