Throughout the years, most top contenders in Kentucky Derby prep races have been colts or geldings. Although fillies are eligible for all Derby preps and can earn points toward securing a spot in the starting gate for the first jewel of the Triple Crown, not many of them take on males along the Derby trail or in the classic.

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The connections of elite fillies historically prefer instead to race against their own sex in the winter and spring while targeting the Kentucky Oaks the day before the Kentucky Derby.

In the past 20 years, only two fillies have competed in the Kentucky Derby: Eight Belles, who finished second in 2008, and Devil May Care, who was 10th in 2010.

In 2013, the Derby unveiled a new qualifying system, in which horses earned points with top-four performances in stakes races. This system also meant that a filly who wanted to get into the Derby had to race against males before the race. Previously, graded stakes earnings in races restricted to fillies counted towards eligibility.

Let's take a look back at some notable fillies who tried their luck in major Kentucky Derby prep races during the past 35 years.

WINNING COLORS, 1988 SANTA ANITA DERBY

By 1988, D. Wayne Lukas had established himself as one of the country’s top trainers. The Kentucky Derby remained an elusive prize for him; he had not yet won it despite entering 12 starters in the seven years prior.

In winning the Santa Anita Oaks, Winning Colors established herself as a Derby prospect. Facing off against three Charlie Whittingham-trained fillies, she crushed them in a dominant gate-to-wire performance by eight lengths. Off that victory, she was the 2.60-1 favorite in the Santa Anita Derby four weeks later.

The outcome was never in doubt. Gary Stevens put Winning Colors on the early lead and she zoomed to a clear advantage through fast fractions. None of her eight rivals had a prayer of catching her, and she crushed the field by 7 ½ lengths in 1:47 ⅘. A month prior, it wasn’t clear if Winning Colors was the best 3-year-old filly in the country. Now, she looked like one of the best 3-year-olds of either sex in the U.S.

In the Kentucky Derby, Winning Colors was one of the co-favorites at 3.40-1 odds. Just like in the Santa Anita Derby, she led from start to finish to become the third filly to win the Kentucky Derby and the first Derby winner for Lukas. On the strength of that accomplishment, she was inducted into the Racing Hall of Fame in 2000.

MEADOW STAR, 1991 WOOD MEMORIAL

Meadow Star (BloodHorse Library)

Few 2-year-old fillies have looked as dominant as Meadow Star did in 1990. She was a perfect 7-for-7 in her freshman campaign, winning four Grade 1 races, including the Breeders’ Cup Juvenile Fillies, by an average margin of 5 1/4 lengths. Her 3-year-old season started off in similar style as she won the Queen of the Stage Stakes and the Grade 2 Comely Stakes by open lengths.

With nothing left to prove against the fillies, trainer Leroy Jolley decided to test her against the boys and entered her in the Grade 1 Wood Memorial Stakes at Aqueduct. It was not only her first start against males, it was her first try around two turns. She was the co-favorite at 2-1 with Cahill Road. A rainy forecast never materialized, and the race was run on a fast track. In the eyes of many, that gave an advantage to Meadow Star.

Chris Antley rated Meadow Star a bit farther off the pace than usual as Gotham Stakes winner Kyle’s Our Man set a clear early lead. That rival began to come back to the field, while Cahill Road, a full brother to 1990 Kentucky Derby winner Unbridled, made his move. Antley followed suit, moving Meadow Star three wide after the leaders, however, the filly had no response for and flattened out to finish fourth in her first loss.

She bounced back in her next two races, winning the Acorn Stakes at Belmont Park by six lengths then prevailing in an epic stretch duel with Lite Light in the Mother Goose Stakes.

SERENA’S SONG, 1995 JIM BEAM STAKES

Heading into the 1995 Jim Beam Stakes at Turfway Park, Serena’s Song had little left to prove against fillies. She had risen to national prominence following a gutsy runner-up performance to stablemate Flanders in the 1994 Breeders’ Cup Juvenile Fillies. After Flanders was sidelined, Serena’s Song became the top filly in D. Wayne Lukas’s barn. She promptly rattled off four wins in a row against fillies in Southern California, prompting Lukas to send her eastward for the Jim Beam Stakes.

She made it look easy. Corey Nakatani put the filly on the lead as the 9-10 favorite and faced pressure in the early stages. It didn’t bother Serena’s Song, and she turned for home with a clear lead. She crossed the finish line 3 ½ lengths in front, ensuring herself a spot in the Kentucky Derby starting gate as the first filly to try the run for the roses since Winning Colors in 1988.

Coupled in the betting with Timber Country, Serena’s Song was the 3.40-1 favorite and set the pace, but she tired badly in the stretch and finished 16th. That race didn’t slow her down, however, as she went on to win 10 more graded stakes in her career, including the Haskell Invitational against males. She was inducted into the Racing Hall of Fame in 2002.

SHARP CAT, 1997 SANTA ANITA DERBY

Sharp Cat had been sharp, indeed, in the winter and spring of her 3-year-old season. She swept through Santa Anita’s stakes races for 3-year-old fillies, capping it off with a 5 ½-length win in the Santa Anita Oaks. She began drawing comparisons to Winning Colors, the Kentucky Derby-winning filly also trained by D. Wayne Lukas almost a decade prior.

In the Santa Anita Derby, Sharp Cat was the slight 2-1 favorite in the 11-horse field, narrowly getting the nod over the Bob Baffert-trained Silver Charm. She went to the lead from the inside post but received pace pressure from Silver Charm. The two zoomed through blazing fractions, setting the opening quarter-mile in :22.19 and the half-mile in :45.15. As they rounded the final turn, they had gone through three-quarters of a mile in a grueling 1:09.15, and the closers began to move in. Silver Charm hung in there and finished second, beaten by a head by Free House. Sharp Cat battled until the last eighth before fading to sixth, beaten by 5 ¾ lengths.

Because the Kentucky Derby did not draw a full field of 20 that year, Lukas could have pressed on to the run for the roses with Sharp Cat if he so wished. However, he entered her against fillies in the Kentucky Oaks, where she was 3-1 odds. She set the early pace and crossed the finish line third, but Sharp Cat was disqualified and placed eighth for causing interference in the stretch. For the rest of her career, Sharp Cat was never worse than second in 10 starts. In December of her 3-year-old year, she made history by winning the Bayakoa Handicap at Hollywood Park in a walkover.

HONEST LADY, 1999 SANTA ANITA DERBY

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The 1999 Santa Anita Derby was Honest Lady’s second start against males on that year’s Derby trail. After starting her career 2-for-2 against fillies, trainer Bobby Frankel decided to try her in the Grade 2 San Rafael Stakes. As the 7-5 favorite, she set a fast pace and battled gamely in the stretch. In a driving finish she finished fifth, beaten by just a length.

Frankel and owner Juddmonte Farms decided the effort was good enough to keep her on the Derby trail, and she was entered in the Santa Anita Derby. She was the 6.30-1 fourth choice in the field of eight, which included eventual Kentucky Derby winner Charismatic. Unlike in the San Rafael, Kent Desormeaux decided to rate Honest Lady off the pace, keeping her on the rail behind moderate fractions. Rounding the final turn, Desormeaux pushed the button but Honest Lady had no response. She faded to finish seventh, beaten by 12 ¼ lengths.

After her Santa Anita Derby try, Honest Lady went to the sidelines until September. Later in her career, she won three more graded stakes races and was second in the 2000 Metropolitan Handicap and 2000 Breeders’ Cup Sprint.

Although Honest Lady did not participate in that year’s Triple Crown, there was no shortage of fillies in the Triple Crown races that season. In the Kentucky Derby, Excellent Meeting finished fifth, while Three Ring was 19th. In the Preakness Stakes, Excellent Meeting was eased and did not finish, while Silverbulletday ran seventh in the Belmont Stakes.

SURFSIDE, 2000 SANTA ANITA DERBY

Hall of Fame trainer D. Wayne Lukas (Eclipse Sportswire)

Hall of Fame trainer D. Wayne Lukas was overstocked with 3-year-olds in 2000. He saddled three horses in that year’s Kentucky Derby, and won the Belmont Stakes with Commendable. On the fillies’ side, he had reigning Breeders’ Cup Juvenile Fillies winner Cash Run in his barn, but she wasn’t even Lukas’s best filly. That distinction belonged to Surfside, a homebred from Overbrook Farm. Surfside was regally bred. Her sire was 1977 Triple Crown winner Seattle Slew. Her dam, Flanders, was the 1994 champion 2-year-old filly.

As a 2-year-old, Surfside won two Grade 1 races and ran third behind her stablemate in the Juvenile Fillies. She started her 3-year-old season with three stakes wins, all of them at odds of 2-5 or less. Despite his already loaded Derby stable, Lukas decided the filly had earned a shot against males and entered her in the Santa Anita Derby.

Breaking from the inside post in the field of six, jockey Pat Day put Surfside on the lead early and set honest fractions. As they rounded the final turn, eventual Breeders’ Cup Mile winner War Chant moved alongside Surfside, giving the filly a stiff challenge. Surfside had no response and she dropped through the pack. She ended up finishing fifth, beaten by 8 ½ lengths.

Surfside got her redemption toward the end of the year. After a summer break, she returned to finish second in the Breeders’ Cup Distaff behind stablemate Spain. She then beat older males in the Clark Handicap by four lengths. On the strength of that effort, she was voted the champion 3-year-old filly at year’s end.

SWEET CATOMINE, 2005 SANTA ANITA DERBY

Trained by Julio Canani, Sweet Catomine was voted the champion 2-year-old filly of 2004 after three graded stakes wins. In the Breeders’ Cup Juvenile Fillies at Lone Star Park, she encountered traffic trouble on the turn but recovered to win going away. In her first two starts as a 3-year-old, she won the Santa Ysabel Stakes and the Santa Anita Oaks by a combined 5 ½ lengths, going off as the prohibitive favorite both times. She was receiving action not only in the Kentucky Oaks future wager but in the Derby Future book as well. In the final future pool for the Derby, Sweet Catomine closed at 13-1.

Her owners, Martin and Pam Wygod, entered her in the Santa Anita Derby, but she bled in a workout six days before the race, spurring a visit to an equine health center. Satisfied with her condition, her connections pressed on. Sweet Catomine went off as the even-money favorite in the field of 11. Corey Nakatani rated her right off the leaders, but had to encourage her to keep up as they rounded the far turn. As they entered the stretch, a hole opened up just off the rail but Sweet Catomine had no response and flattened to finish fifth.

After the race, Sweet Catomine was transferred to the barn of John Sherriffs and then was retired two weeks later.

SWISS SKYDIVER, 2020 TOYOTA BLUE GRASS STAKES

Multiple Grade 1 winner Swiss Skydiver, winner of the Grade 1 Preakness Stakes against males Oct. 3 at Pimlico Race Course. (Eclipse Sportswire)

The COVID-19 pandemic turned the Derby trail on its head in 2020. The big race was moved to September, resulting in the re-shuffling of many Derby preps. The Keeneland spring meet was canceled, and many of the big stakes of the meet were moved to a special week of racing in mid-July, including the Toyota Blue Grass Stakes.

One of the 13 entrants in last year’s Blue Grass Stakes was Swiss Skydiver. She went into the race riding a three-race winning streak, including an easy four-length win in the Santa Anita Oaks the race prior. That winning streak had given her enough points to ensure a spot in the Longines Kentucky Oaks later in the year, so trainer Ken McPeek decided to give her a shot against males in the Blue Grass. She became the first filly to run in the Blue Grass since 1944, when Harriet Sue finished fifth.

Swiss Skydiver went off as the slight 2.20-1 favorite. She engaged for the lead early with Shivaree, then established control as they moved toward the half-mile point. As they rounded the final turn, Art Collector, who had rated just off the leaders, moved to engage the filly in battle. The two dueled down the stretch and, in the last sixteenth, Art Collector got the upper hand and prevailed by 3 ½ lengths. Swiss Skydiver wound up second, 4 ½ lengths clear of third-place Rushie.

Although she was second in the Longines Kentucky Oaks later that year, Swiss Skydiver got her win against the males in the Preakness Stakes. After an epic battle with eventual Horse of the Year Authentic down the Pimlico stretch, Swiss Skydiver prevailed by a neck to become the second filly to win the Preakness in the past 90 years.