The Fabulous Fillies of the Kentucky Derby Quiz

Answer: 1870s & 1910s

The first Kentucky Derby was in 1875, and in the first five Derbys there were no less than 7 fillies starting. Another seven started in the 1910s. The 1920s and 1930s each boasted six fillies starting in the Derby. There were 3 starting fillies apiece in the 1980s and 1990s.

There was only one filly in the 1880s, Pike's Pride (1883); in the 1940s, Misweet (1945); in the 1950s, Silver Spoon (1959); and in the 2000s, Eight Belles (2008). No fillies entered the Kentucky Derby in the 1890s or the 1960s.

Answer: Lady Navarre

Lady Navarre finished second to Sir Huon in the 32nd Kentucky Derby in 1906 in a field of six horses. She was the first filly even to start in the Derby since 1883 (a 23-year gap). The 32nd Derby was the first one timed to fifths of a second rather than fourths. Lady Navarre was also the first filly to run in both the Kentucky Oaks (the Derby's fillies-only sister race) and the Kentucky Derby. Lady Navarre finished second again to Sir Huon in the Latonia Derby.

Ascension and Gold Mine were the first fillies ever to start in the Kentucky Derby. They raced in 1875 at the very first Derby and finished 10th and 15th to Aristides. Lizzie Stone finished sixth in the second Kentucky Derby ever held (1876), losing to Vagrant, who carried only 97 pounds (in modern Kentucky Derbys the weight is 126 pounds for all horses).

Answer: Regret

Regret was a chestnut filly foaled in New Jersey. She broke her maiden at first asking in the 1914 Saratoga Special. An exceptionally large filly, Regret raced only against colts, never other fillies.

Regret's win came at time when some unusual things happened at the Kentucky Derby to make it hit the front pages of the newspapers. In 1913, the long-shot Donerail won at 91-1, paying $184.90 on a $2 bet and setting a record for the longest odds that stood well into the 21st century. The following year, Old Rosebud set a speed record for the Derby at 2:03, and kept that record for sixteen years. Then in 1915, the muscular filly Regret won. Matt J. Winn, owner of Churchill Downs and the "Kentucky Derby" name in the 1910s, once remarked: "The race needed only a victory by Regret to create some more coast-to-coast publicity to really put it over. She did not fail us. Regret made the Kentucky Derby an American institution."

Regret was inducted into the National Museum of Racing and Hall of Fame in 1957.

Answer: Silver Spoon

Silver Spoon's sire was Citation and her dam was Silver Fog, who carried the blood of Man o' War, Peter Pan, Blenheim II, and many other impressive ancestors. A large chestnut filly with four stockings, Silver Spoon stood over 16 hands tall. An injury as a foal left her with a hitch in her gate, but she nevertheless dominated in races on the West Coast of the USA, and took the Santa Anita Derby against colts. Only Winning Colors and Silver Spoon have won both the Santa Anita Derby and the Santa Anita Oaks (formerly the Santa Susana Stakes).

The press hailed her as the best filly since World War II. No filly had attempted the Derby since Misweet finished 12th in 1945.

Answer: Genuine Risk

Genuine Risk won the 1980 Kentucky Derby against a field of twelve colts. She broke well and held back behind Plugged Nickle and inside Withholding around the first turn and the backstretch. Then she moved to the outside at the half-mile pole, and took the lead entering the home stretch. Ridden by Jacinto Vasquez, this chestnut mare took the Kentucky Derby a full 65 years after Regret won the garland of roses in 1915. She was mated to Secretariat, and the foal would have been the first ever offspring of two Kentucky Derby winners; hopes were dashed, however, when Genuine Risk delivered a stillborn colt. Genuine Risk was inducted into the National Museum of Racing and Hall of Fame in 1986.

Regret was the first filly to win the Kentucky Derby (1915).

Answer: Winning Colors

Winning Colors was gray with a white blaze (though she was registered as a roan) and trained by D. Wayne Lukas. Ridden by Gary Stevens in the 114th Kentucky Derby, she faced a stellar field of horses including Forty Niner, Regal Classic, and Private Terms. She broke alertly and went straight for the lead. Although Forty Niner gave Winning Colors a chase at the home stretch, she beat him by a neck. At age four she developed breathing difficulties and retired after seven races that year. Winning Colors received the 1988 Eclipse Award for Outstanding 3-Year-Old Filly, and she was inducted into the National Museum of Racing and Hall of Fame in the year 2000.

Regret was the first filly to win the Kentucky Derby (1915), and Genuine Risk was the second (1980).

Answer: 1870s

Two fillies starting in a race was actually a frequent phenomenon in those first five years of the Kentucky Derby. In 1875, two fillies, Ascension (19th place) and Gold Mine (15th place) started at the first Run for the Roses, losing to Aristides. The very next year, Marie Michon (7th) and Lizzie Stone (6th) ran. In 1879, there were Ada Glenn (7th) and Wissahickon (9th).

It happened twice in the 1920s. In 1920, Cleopatra and Regalo tied for 15th place, and in 1921 Prudery (the favorite) and Careful finished third and fifth. Other decades saw double fillies only once. In 1934, Mata Hari and Bazaar finished 4th and 9th, respectively. In 1984, Life's Magic and Althea, part of the same entry, were both favorites, but they finished 8th and 19th. Lastly, in 1999, Excellent Meeting and Three Ring finished 5th and 19th.

Given the change in 2013 to the new points system to qualify for the Derby, it is not likely that this phenomenon will be repeated, as there are no fillies-only races on the official Road to the Kentucky Derby.

Answer: Flamma

Before the end of World War II, the Kentucky Oaks was normally run after the Kentucky Derby. In the twentieth century, five fillies parlayed their Derby efforts into a Kentucky Oaks championship. The first was Flamma, who came in third of seven starters in the 38th Kentucky Derby.

She had been restless at post and broke badly out of the gate, but closed a big gap to finish five lengths in the mud behind the winner Worth. She conquered the Oaks, however, just seventeen days later, over another muddy track. Likewise Bronzewing in 1914 finished a distant third to Old Rosebud, but 13 days later she rebounded to sweep the Kentucky Oaks. Viva America (1918, 3rd in the Derby), Startle (1922, 8th), and the great broodmare Alcibiades (1930, 10th) similarly turned defeat into victory by taking the Oaks.

Answer: Prudery

Although she was the favorite, Prudery finished third to Behave Yourself in the 47th Kentucky Derby in 1921. A week later Prudery lost by barely a head to Nancy Lee in the Kentucky Oaks. Later that summer Prudery won the Alabama before finishing second in the Travers Stakes at Saratoga to the Belmont runner-up, Sporting Blood.

Nellie Flag was the favorite in 1935, finishing 4th to Omaha. Co-favorites Life's Magic and Althea (part of the same entry) finished 8th and 19th behind Swale in 1984. Life's Magic had earlier won the Mother Goose stakes, and in 1985 she defeated Lady's Secret to win the Breeder's Cup Distaff. Life's Magic won an Eclipse Award twice, at age 3 and age 4.

Smaller than average Serena's Song was the favorite in 1995, but finished 16th behind Thunder Gulch; however, that same year she won the Mother Goose Stakes, the Santa Anita Derby, and the Haskell Invitational Handicap. At age 10, Serena's Song was inducted into the Hall of Fame in 2002.

Answer: Eight Belles

Prior to the Kentucky Derby, Eight Belles became the first filly to win the Martha Washington Stakes, the Honeybee Stakes, and the Fantasy Stakes at Oaklawn Park in Arkansas in 2008. At the Derby, she pulled up in distress about a furlong (220 yards or 200 m) after crossing the wire.

As she was suffering greatly from fractures of the cannon and sesamoid bones in both front legs, the on-call veterinarian euthanized her on the track. These injuries were the same sort of break that 2006 winner Barbaro endured in one leg, before he was also put down.

In her honor, Churchill Downs renamed the La Troienne Stakes the Eight Bells Stakes in 2009, which was run on the undercard of Derby Day and then moved to Oaks Day in 2013.