The Preakness Stakes has long been a proving ground for the toughest and most talented 3-year-olds each year. Run two weeks after the Kentucky Derby, colts have traditionally dominated this middle jewel of the Triple Crown, but its 150-year history has seen a few fillies rise to the challenge and etch their names into history.

Wearing the blanket of Black-Eyed Susans requires speed, stamina, and heart  —qualities these exceptional fillies displayed in abundance. From Flocarline in 1903 to Swiss Skydiver in 2020, here is a look at the six remarkable fillies who have triumphed in the Preakness Stakes.

1903 – Flocarline (St. Florian – Carline, by King Ban)

1903 Preakness winner Flocarline (Keeneland Library Collection)

Bred in Kentucky by Charles McMeekin of Oakwood Farm, this leggy chestnut filly was by the stakes winner St. Florian out of the mare Carline, a daughter of a minor stakes winner in England. Named Flocarline, she was purchased at a New York yearling sale for $150 by Frank Farrell, and even though she looked like “a wornout feather duster,” M.H. Tichenor bought the promising filly from Farrell for $500. She won her debut and Tichenor sent her previous owner another $500 in appreciation.

She raced in the Midwest and California, winning the Preliminary Derby in New Orleans and another at Ingleside in San Francisco. Her record was such that Tichenor fielded offers of $10,000 and $12,000 for Flocarline at age 2, but he turned them down to continue racing this excellent filly.

After a juvenile season with nine wins, including two stakes, the filly went east to New York and was part of the Preakness Stakes field at Gravesend. Facing a field of five others, she went to the front from the break, fell behind Rightful after a half-mile, but stayed close enough to fight for the lead in late stretch and win by a half-length over the favored Mackey Dwyer. Her time of 1:44 4/5 clipped a full second off the stakes record for the one-mile and 70-yard Preakness.

Six weeks after her win, Flocarline was part of Tichenor’s dispersal sale at Washington Park in Chicago. She sold for $6,100 to Samuel S. Brown of Senorita Farm and then sold again in 1908 to T. F. Kelly for $3,100. As a broodmare, the first filly to win the Preakness produced 13 foals, including stakes winner Master Robert.

1906 – Whimsical (Orlando – Kismet, by Hindoo)

Catesby Woodford’s Raceland Farm collaborated with his friend Col. Ezekial Clay’s Runnymede Farm to produce a number of great horses in the latter years of the 19^th century. Names like Hanover, Miss Woodford, Ben Brush, and others all came from this partnership, their joint efforts producing another classic winner, the filly Whimsical.

Woodford purchased her sire, Orlando, from owner Lord Beresford after the bay stallion’s stakes-winning career in England, where he won the Dewhurst Plate at age 2 and the Eclipse Stakes at 3 and 4, and then bred him to his mare Kismet to produce a chestnut filly who would add her name to a historic list in her 3-year-old season.

As a yearling, she was sold to Timothy Gaynor for $500, who trained his “slashing big chestnut” himself through her 2-year-old season. She won the Golden Rod and Belles Stakes that year and was second behind the colt Perverse in the Champagne Stakes. She ended 1905 as the leading 2-year-old filly that season, leaving Gaynor’s hopes high that 1906 would yield more of the same.

She was one of 10 who faced the barrier in late May for the Preakness Stakes at Gravesend. Just the month before, she had battled Roseben and other older horses in the seven-furlong Carter Handicap at Aqueduct, finishing third behind the Hall of Famer. With jockey Walter Miller in the saddle, she took the lead from the drop of the flag and held the field at bay throughout. At the wire, she was six lengths in front, this daughter of Orlando the second filly to win the Preakness Stakes.

Whimsical raced for another season before retiring to broodmare life at Harry Payne Whitney’s Brookdale Farm, producing several foals before passing away in 1915.

1915 – Rhine Maiden (Watercress – Gold, by Golden Garter)

Bred by James Ben Ali Haggin’s Elmendorf Farm in Kentucky, the bay daughter of Watercress, an English stakes winner, was purchased by banker Edward F. Whitney at a Sheepshead Bay yearling auction for $700. As a 2-year-old, she won the Heyday Purse, a stakes race at Piping Rock Country Club on Long Island, which held brief meets in 1913, 1914, and 1915.

At 3, her signature win came in the Preakness Stakes, which was listed as the Preakness Handicap in 1915. The race had returned to Pimlico in 1909 and was still a few years away from gaining the importance that it enjoys today. A little more than a week after Regret became the first filly to win the Kentucky Derby, Rhine Maiden faced a field of just five others over a muddy Pimlico strip. The daughter of the Haggin broodmare Gold took the lead early and sailed to a 1 ½-length win. Her victory made 1915 the only year where fillies won two of the three Triple Crown classics. She also won the Glen Cove Plate at Piping Rock that season.

Rhine Maiden raced for two more seasons, winning the Ladies Handicap and then meeting Regret in the 1917 Gazelle Handicap. She finished fourth behind the Derby winner and then retired to broodmare life at the end of the season. Rhine Maiden produced one foal, Rhinegold, before passing away in 1923 at the age of 11.

1924 – Nellie Morse (Luke McLuke – La Venganza, by Abercorn)

Nellie Morse under jockey Earl Sande (Keeneland Library Cook Collection)

The first filly to win the Preakness Stakes after Sir Barton’s pioneering 1919 Triple Crown was Nellie Morse. A daughter of Belmont Stakes winner Luke McLuke, the bay filly had a unique start to her life: her breeder Jack Keene sent her dam La Venganza to a local tobacco farmer while she was in foal. The mare had not produced a good horse in some time and the breeder was looking to rehome her after she had her foal. After she bore a filly, Keene asked the farmer to keep the foal confined to her barn rather than run around on a farm lined with barbed wire and strewn with equipment.

As a yearling, Keene sent the Luke McLuke filly to the 1922 Saratoga yearling sale, where she sold for $2,000 to cartoonist Harry Conway “Bud” Fisher, creator of the “Mutt and Jeff” comics. Named Nellie Morse after Fisher’s mother, she went to the barn of Alex Gordon for her racing career, this tough, hard-trying filly starting 22 times in her 2-year-old season. That year, she won or placed in several stakes, including a win in the Fashion Stakes and a second in the Spinaway Stakes.

At 3, Nellie Morse had a trio of big-name performances in a short span of time. In early May at Pimlico, she took over the lead at the six-furlong mark in the Pimlico Oaks, now known as the Black-Eyed Susan, and outlasted a relentless run from a filly named Relentless to win the race by a head. Four days later, she was back at the Pimlico starting line for the 28^th Preakness Stakes. Facing a large field that included stakes winners like Bracadale and Mad Play, the filly took advantage of a sloppy track to grab an early lead and hold off Transmute late to win this classic by 1½ lengths. Not done, Fisher sent the filly to Churchill Downs for the Kentucky Oaks on May 31. Interference from the eventual winner Glide impeded Nellie Morse’s hold on the lead in the stretch; Glide’s disqualification elevated her from third to second behind Princess Doreen.

Nellie Morse went on to race at age 4 but was unable to recapture the form that saw her become the fourth filly to win the Preakness Stakes. As a broodmare, she produced two foals by Sporting Blood for Fisher, who then paired her with American Flag, a son of Man o’ War. When Fisher decided to disperse all of his bloodstock, Nellie Morse hammered down for $6,100 to Calumet Farm’s Warren Wright. The following year, 1932, Nellie Morse foaled a bay filly that Wright would name Nellie Flag. She would become Calumet’s first Kentucky Derby starter in 1935.

2009 – Rachel Alexandra (Medaglia d’Oro – Lotta Kim, by Roar)

Her sire, Medaglia d’Oro, was a Grade 1 winner who finished second in the 2002 Belmont Stakes and her dam, Lotta Kim, was a listed stakes winner, but Rachel Alexandra eclipsed even her Travers-winning father.

Rachel Alexandra winning the 2009 Preakness Stakes. (Eclipse Sportswire)

At 2, she won three of her six starts, including the Grade 2 Golden Rod Stakes at Churchill Downs, for breeder-owner Dolphus Morrison, who had named the bay filly for his granddaughter. At 3, Rachel Alexandra was on the Kentucky Oaks trail, Morrison preferring to keep his filly in her division rather than race her against the boys. She won three stakes in her preparation for the first Friday in May, but her performance in the Kentucky Oaks nearly overshadowed Mine That Bird’s upset in the Derby the next day. Rachel Alexandra won by an eye-opening 20 ¼ lengths, leaving fans wondering what she could have done had she run for roses rather than lilies.

Right after the Oaks, Jess Jackson and Harold McCormick bought the filly for a reported $10 million, switching her from the barn of Hal Wiggins to Hall of Famer Steve Asmussen. Her new owners supplemented their filly to the Preakness Stakes, where she would face Mine That Bird and Derby runner-up Pioneerof the Nile, among others. She took the lead from the start, showing her heels to the boys early and then holding off Mine That Bird’s late bid to win the 134^th Preakness Stakes.

The rest of her 2009 campaign was nothing short of extraordinary: Rachel Alexandra won the Mother Goose by 19 ¼ lengths and the Haskell over 3-year-old males before trying older horses in the Grade 1 Woodward Stakes at Saratoga. After assuming control early, she went into the far turn with a length advantage, but in the straightaway, Bullsbay and Macho Again challenged, both inching closer as the finish line loomed. Jockey Calvin Borel worked hard to get his filly to hold on to her shrinking lead, crossing the finish line a head in front of Macho Again, that stretch run raising the rafters at the Spa. Her blockbuster season earned her not only an Eclipse as champion 3-year-old filly, but also Horse of the Year.

At 4, Rachel Alexandra won two of her five starts and then retired to broodmare life at Stonestreet Farm in Kentucky. She produced two foals, Jess’s Dream and Rachel’s Valentina, before health issues forced her retirement from breeding. She still resides at Stonestreet, drawing a legion of admirers to see ‘Alexandra the Great’ each year.

2020 – Swiss Skydiver (Daredevil – Expo Gold, by Johannesburg)

The COVID-19 pandemic of 2020 meant a temporary shift in the racing calendar, moving the Preakness Stakes from mid-May to early October. This presented a unique opportunity for this daughter of a Daredevil.

Swiss Skydiver, right, holds off Derby winner Authentic in Preakness. (Eclipse Sportswire)

Purchased for $35,000 at the 2018 Keeneland September yearling sale, trainer Kenny McPeek saw potential in the chestnut daughter of Grade 1 winner Daredevil out of Expo Gold, by 2001 Breeders’ Cup Juvenile winner Johannesburg. She won her debut at Churchill Downs and then finished second in her other 2-year-old start in 2019. The following year, Swiss Skydiver, named for owner Peter Callahan’s granddaughter Callie, won the Grade 2 Gulfstream Oaks in late March and then McPeek shifted her calendar as the Kentucky Oaks was rescheduled from early May to the first weekend of September. The filly won the Santa Anita Oaks in June, finished second to Art Collector in the Blue Grass Stakes in July, and then won the Grade 1 Alabama Stakes at Saratoga.

Swiss Skydiver came up short against Shedaresthedevil, also sired by Daredevil, in the Grade 1 Kentucky Oaks, and McPeek, who knew his filly had already beaten most of the horses in her division, opted to send her to Pimlico for the Preakness rather than the Black-Eyed Susan Stakes. On Oct. 3, the filly faced Kentucky Derby winner Authentic, Art Collector, Max Player, and Thousand Words among others in the Grade 1 Preakness. She broke cleanly, stuck her head in front briefly, and then settled in behind Authentic and Thousand Words. On the backstretch, she took advantage of the slow pace to go from fifth to first as they headed into the far turn.

She and Authentic hooked up as they rounded the bend and hit the top of the stretch together, dueling down the Pimlico stretch. Each time she put any space between them, he would battle back, the two crossing the finish line together. Swiss Skydiver got the win by a neck, defeating the Derby winner and sealing her name in the history books as one of six fillies to win the middle jewel of the Triple Crown. Her stellar season earned her the Eclipse Award as champion 3-year-old filly.

She won the Grade 1 Beholder Mile at age 4 to open the season but did not win again in three subsequent starts in 2021, going through the auction ring at th eKeeneland November breeding stock sale and selling for $4.7 million to Katsumi Yoshida. She is now part of the broodmare band at Yoshida’s Northern Farm in Japan.