Historically, the majority of leading participants in preliminary contests for the Kentucky Derby, sponsored by Woodford Reserve, have comprised male horses or castrated males. While female horses are permitted to enter any Derby preparatory event and accrue points to qualify for the initial leg of the Triple Crown, very few choose to compete against their male counterparts during the Derby lead-up or in the main race itself.
Owners and trainers of outstanding female horses have traditionally opted for them to contend solely against other fillies throughout the winter and spring seasons, with their primary aim being the Kentucky Oaks, held the day preceding the Kentucky Derby.
Over the last two decades, merely a pair of fillies have participated in the Kentucky Derby: Eight Belles, securing the runner-up position in 2008, and Devil May Care, who placed tenth in 2010.
A revised eligibility framework for the Derby was introduced in 2013, where thoroughbreds accumulated points through finishing among the top four in stakes competitions. Consequently, this structure dictated that any filly aspiring to enter the Derby lineup would be required to compete against colts prior to the main event. Prior to this change, earnings from graded stakes races exclusively for fillies contributed to their qualification.
We will now revisit several distinguished fillies who ventured into prominent Kentucky Derby trial races over the last three and a half decades.
WINNING COLORS, 1988 SANTA ANITA DERBY
By the year 1988, D. Wayne Lukas had cemented his reputation as one of the nation’s premier horse trainers. However, the Kentucky Derby title continued to evade him; he had not claimed victory in the race, despite having fielded twelve contenders in the preceding seven years.
Winning the Santa Anita Oaks solidified Winning Colors’ status as a potential Derby runner. Competing against three fillies under the guidance of Charlie Whittingham, she decisively overpowered them with a commanding wire-to-wire run, finishing eight lengths ahead. Following that triumph, she was installed as the 2.60-1 betting favorite for the Santa Anita Derby, held four weeks subsequent.
The result of the race was utterly conclusive. Gary Stevens positioned Winning Colors at the forefront from the outset, and she swiftly accelerated to a distinct lead, maintaining rapid sectional times. None of her eight competitors stood any chance of overtaking her, and she thoroughly defeated the lineup by a margin of 7 ½ lengths, clocking 1:47 ⅘. Just a month earlier, there was uncertainty as to whether Winning Colors was the top three-year-old filly nationwide. Presently, she appeared to be among the elite three-year-olds regardless of gender in the United States.
During the Kentucky Derby, Winning Colors shared the favoritism at odds of 3.40-1. Mirroring her Santa Anita Derby performance, she maintained the lead from beginning to end, thereby becoming the third filly to claim the Kentucky Derby title and D. Wayne Lukas’s inaugural Derby triumph. In recognition of this significant achievement, she was enshrined in the Racing Hall of Fame in the year 2000.
MEADOW STAR, 1991 WOOD MEMORIAL
In 1990, hardly any two-year-old fillies exhibited the sheer superiority displayed by Meadow Star. She achieved an unblemished record of seven wins from seven starts in her initial racing year, securing four Grade 1 victories, among them the Breeders’ Cup Juvenile Fillies, with an average winning margin of 5 1/4 lengths. Her three-year-old campaign commenced in a comparable fashion, as she captured the Queen of the Stage Stakes and the Grade 2 Comely Stakes by substantial distances.
Having nothing further to demonstrate against female competition, trainer Leroy Jolley opted to pit her against male horses, entering her in the Grade 1 Wood Memorial Stakes at Aqueduct. This marked not only her inaugural race against colts but also her first attempt at a two-turn distance. She was priced as a co-favorite at 2-1 alongside Cahill Road. Although rain had been predicted, it did not occur, and the race proceeded on a fast track. This circumstance was widely perceived to benefit Meadow Star.
Chris Antley positioned Meadow Star slightly further from the leading pace than was customary, as Kyle’s Our Man, victor of the Gotham Stakes, established a distinct early lead. As that competitor started to tire and rejoin the main group, Cahill Road, a full sibling to Unbridled, the 1990 Kentucky Derby champion, initiated his run. Antley responded by guiding Meadow Star three-wide in pursuit of the front-runners; however, the filly failed to quicken and faded, settling for a fourth-place finish in what was her first defeat.
She subsequently rebounded in her following two engagements, triumphing in the Acorn Stakes at Belmont Park by six lengths, and then securing victory in a memorable final-stretch contest against Lite Light in the Mother Goose Stakes.
SERENA’S SONG, 1995 JIM BEAM STAKES
Prior to the 1995 Jim Beam Stakes at Turfway Park, Serena’s Song had virtually nothing remaining to establish herself against her female peers. She had achieved widespread recognition after a courageous second-place finish behind her stable companion, Flanders, in the 1994 Breeders’ Cup Juvenile Fillies. With Flanders subsequently sidelined, Serena’s Song emerged as the leading filly within D. Wayne Lukas’s training operation. She swiftly accumulated four consecutive victories competing against fillies in Southern California, which led Lukas to dispatch her east for the Jim Beam Stakes.
Her performance appeared effortless. Corey Nakatani positioned the filly at the head of the field, with her as the 9-10 favorite, and she encountered early challenges. This did not unsettle Serena’s Song, and she entered the final stretch with a distinct advantage. She crossed the wire 3 ½ lengths ahead, thereby guaranteeing her entry into the Kentucky Derby starting field, marking her as the first filly to attempt the ‘Run for the Roses’ since Winning Colors in 1988.
As a combined betting entry with Timber Country, Serena’s Song held favoritism at 3.40-1 odds and established the early tempo, but she faltered considerably in the homestretch, concluding the race in 16th place. Nevertheless, that particular race did not hinder her subsequent career; she proceeded to claim victory in ten additional graded stakes events, notably the Haskell Invitational when competing against male horses. She received induction into the Racing Hall of Fame in 2002.
SHARP CAT, 1997 SANTA ANITA DERBY
Sharp Cat had demonstrated remarkable prowess throughout the winter and spring segments of her three-year-old campaign. She dominated Santa Anita’s stakes races designated for three-year-old fillies, culminating in a decisive 5 ½-length triumph in the Santa Anita Oaks. Observers started likening her to Winning Colors, the filly who won the Kentucky Derby and was also trained by D. Wayne Lukas, nearly ten years earlier.
For the Santa Anita Derby, Sharp Cat was the narrow 2-1 favorite among the eleven contenders, just edging out the Bob Baffert-trained Silver Charm. She assumed the lead from her inside starting position but was immediately challenged for pace by Silver Charm. The pair charged through incredibly fast early splits, recording the first quarter-mile in :22.19 and the half-mile in :45.15. By the time they rounded the final bend, they had covered three-quarters of a mile in a demanding 1:09.15, at which point late-runners began their surge. Silver Charm persevered to claim second, defeated by a head by Free House. Sharp Cat contended fiercely until the final furlong before weakening to sixth place, 5 ¾ lengths adrift.
Given that the Kentucky Derby that year did not attract its maximum complement of 20 starters, Lukas had the option to advance Sharp Cat to the prestigious ‘Run for the Roses’ had he desired. Instead, he nominated her to compete against other fillies in the Kentucky Oaks, where she was offered at 3-1 odds. She established the early tempo and passed the wire in third position, but Sharp Cat was subsequently demoted to eighth due to causing interference during the stretch drive. For the remainder of her racing career, Sharp Cat achieved nothing less than a second-place finish in her subsequent ten outings. In December of her three-year-old season, she achieved a unique distinction by winning the Bayakoa Handicap at Hollywood Park unchallenged in a walkover.
HONEST LADY, 1999 SANTA ANITA DERBY
The Santa Anita Derby in 1999 marked Honest Lady’s second appearance against male horses during that season’s Derby preparatory series. Following a flawless 2-for-2 beginning to her career solely against fillies, trainer Bobby Frankel elected to enter her in the Grade 2 San Rafael Stakes. As the 7-5 favorite, she dictated a rapid pace and fought resolutely in the final stages. In a determined finish, she ended up fifth, trailing by merely one length.
Frankel and Juddmonte Farms, the owners, deemed her performance sufficient to maintain her on the Derby path, leading to her entry in the Santa Anita Derby. She was the fourth betting option at 6.30-1 in the eight-horse lineup, which featured Charismatic, who would later win the Kentucky Derby. Differing from her strategy in the San Rafael, Kent Desormeaux chose to position Honest Lady away from the early speed, maintaining her along the rail behind measured splits. As they navigated the final bend, Desormeaux urged her on, but Honest Lady offered no acceleration. She gradually dropped back to finish seventh, trailing by 12 ¼ lengths.
Following her attempt in the Santa Anita Derby, Honest Lady was withdrawn from racing until September. Subsequently in her career, she secured victories in three additional graded stakes and attained second place in both the 2000 Metropolitan Handicap and the 2000 Breeders’ Cup Sprint.
While Honest Lady did not contend in the Triple Crown series that particular year, a notable number of fillies did feature in the Triple Crown events of that season. In the Kentucky Derby, Excellent Meeting achieved a fifth-place finish, whereas Three Ring came in 19th. During the Preakness Stakes, Excellent Meeting was pulled up and failed to complete the race, while Silverbulletday placed seventh in the Belmont Stakes.
SURFSIDE, 2000 SANTA ANITA DERBY
In the year 2000, legendary trainer D. Wayne Lukas possessed an abundant roster of three-year-old thoroughbreds. He presented three horses in the Kentucky Derby that season and triumphed in the Belmont Stakes with Commendable. Among his female contingent, he had Cash Run, the then-current Breeders’ Cup Juvenile Fillies champion, but she was not even considered Lukas’s premier filly. That honor belonged to Surfside, a horse bred by Overbrook Farm. Surfside boasted an exceptional pedigree, sired by the 1977 Triple Crown winner Seattle Slew, and her dam, Flanders, was the recognized champion two-year-old filly of 1994.
During her two-year-old campaign, Surfside secured victories in two Grade 1 events and finished third, behind her barn mate, in the Juvenile Fillies. Her three-year-old season commenced with three stakes victories, each achieved at short odds of 2-5 or lower. Notwithstanding his already formidable collection of Derby contenders, Lukas determined that the filly merited an opportunity to compete against male horses and subsequently entered her in the Santa Anita Derby.
Starting from the innermost position within the six-horse field, jockey Pat Day placed Surfside in the early lead, dictating a reasonable pace. As they navigated the final bend, War Chant, who would later win the Breeders’ Cup Mile, drew even with Surfside, presenting a rigorous test for the filly. Surfside proved unable to respond and gradually fell back through the field. She ultimately concluded the race in fifth place, trailing by 8 ½ lengths.
Surfside achieved her vindication near the conclusion of the year. Following a summer hiatus, she reappeared to secure second place in the Breeders’ Cup Distaff, just behind her stablemate Spain. Subsequently, she overcame older male competitors in the Clark Handicap by a four-length margin. Bolstered by that performance, she was honored as the champion three-year-old filly at the close of the year.
SWEET CATOMINE, 2005 SANTA ANITA DERBY
Under the tutelage of Julio Canani, Sweet Catomine earned the title of champion two-year-old filly for 2004, following three graded stakes victories. During the Breeders’ Cup Juvenile Fillies at Lone Star Park, she faced congestion around the turn but managed to rally and win decisively. In her initial two outings as a three-year-old, she triumphed in the Santa Ysabel Stakes and the Santa Anita Oaks, with a cumulative winning margin of 5 ½ lengths, being the overwhelming favorite on both occasions. Betting activity for her extended beyond the Kentucky Oaks future wager to include the Derby Future book. In the conclusive future pool for the Derby, Sweet Catomine’s odds settled at 13-1.
Her owners, Martin and Pam Wygod, nominated her for the Santa Anita Derby, but she experienced a bleeding incident during a workout six days before the event, prompting an evaluation at an equine medical facility. Content with her health status, her team decided to proceed. Sweet Catomine was sent off as the even-money favorite among the eleven contenders. Corey Nakatani positioned her directly behind the front-runners, but found himself needing to urge her to maintain her position as they navigated the far turn. Upon entering the homestretch, an opening appeared just off the rail, yet Sweet Catomine failed to accelerate and steadily lost ground, ultimately finishing fifth.
Subsequent to the race, Sweet Catomine was moved to John Sherriffs’ stable before being retired from competition two weeks thereafter.
SWISS SKYDIVER, 2020 TOYOTA BLUE GRASS STAKES
The global COVID-19 health crisis significantly disrupted the Kentucky Derby qualification process in 2020. The marquee race itself was postponed until September, which necessitated a widespread reorganization of numerous Derby preparatory events. The traditional Keeneland spring meeting was called off, leading to the relocation of several major stakes races from that schedule to a dedicated week of competition in mid-July, among them the Toyota Blue Grass Stakes.
Among the thirteen participants in last year’s Blue Grass Stakes was Swiss Skydiver. She arrived at the race on the strength of a three-race consecutive winning run, highlighted by a facile four-length victory in the Santa Anita Oaks in her preceding start. That series of wins had garnered her sufficient points to secure a place in the Longines Kentucky Oaks later that year, prompting trainer Ken McPeek to allow her to compete against male rivals in the Blue Grass. She thus became the first female horse to contest the Blue Grass since 1944, when Harriet Sue secured fifth place.
Swiss Skydiver was dispatched as the narrow 2.20-1 betting favorite. She contended for the early lead with Shivaree, subsequently asserting dominance as they approached the halfway mark. Upon navigating the final bend, Art Collector, who had been positioned just behind the leaders, advanced to challenge the filly. The pair engaged in a fierce struggle through the homestretch, and in the ultimate sixteenth of a mile, Art Collector gained the advantage, winning by 3 ½ lengths. Swiss Skydiver ultimately secured second place, a clear 4 ½ lengths ahead of Rushie, who finished third.
Despite her second-place finish in the Longines Kentucky Oaks later that season, Swiss Skydiver earned her victory against male competitors in the Preakness Stakes. Following a monumental duel with Authentic, who would later be named Horse of the Year, along the Pimlico straight, Swiss Skydiver triumphed by a neck, becoming only the second filly to win the Preakness in the preceding nine decades.
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