The Longines Kentucky Oaks is the marquee race for 3-year-old fillies and the sister race to the Kentucky Derby Presented by Woodford Reserve, taking place on the Friday before the run for the roses each year. Although it may not have the name recognition of the Derby, winning the Oaks is a very nice feather in any trainer’s, jockey’s or owner’s cap, and the race often plays a big part in deciding champion 3-year-old filly honors at the end of the year. Read on to reminisce about six editions of the race made memorable for unique reasons.

In 2009, Rachel Alexandra rolled into the month of May on an impressive four-race win streak, leading some to suggest she should take on males in the Kentucky Derby rather than drub another field of overmatched fillies in the Oaks. Her owners were adamant about keeping her competing against her own gender, though, and she put on a show in the Oaks, galloping to a record 20 ¼-length win over six other fillies. Rachel Alexandra was sold after that race and later defeated males on three separate occasions, but her record-breaking Kentucky Oaks win was a defining victory in her legendary season.

Hall of Fame trainer Woody Stephens considered running champion 2-year-old filly Heavenly Cause against the boys in the 1981 Kentucky Derby, but instead he opted for the Oaks and gave fans one of the more exciting editions of the race. Heavenly Cause outdueled her stablemate De La Rose to win by a nose, with Wayward Lass finishing third. Race favorite Truly Bound finished fourth in her quest to stretch her unbeaten streak to seven. De La Rose was named champion turf female that year, and Wayward Lass dominated the second half of the season to be named champion 3-year-old filly. The top three finishers in the 1981 Kentucky Oaks were not only all named champion at one point or another, they also all had stakes races named after them.

The 2006 edition of the Kentucky Oaks featured a full field of 14 horses, including Ashland Stakes winner Bushfire, who would later win both the Acorn and Mother Goose Stakes, and eventual champion Wait a While. Lemons Forever had only a third-place finish in the Bourbonette Oaks to her credit and was dismissed at 47.10-1, the longest shot in the field. Early in the race she ran to her odds, but heading into the turn for home something remarkable happened. Lemons Forever began picking off horses one by one, rolling into 10^th place then fifth, and finally, first, winning the Kentucky Oaks by 1 ½ lengths and paying a record $96.20 for every $2 bet. She never won another stakes but has proven valuable in the breeding shed with two Grade 1 winners to her credit.

Davona Dale (Keeneland Library)

Hall of Famer Davona Dale was one of the most spectacular fillies to win the Kentucky Oaks. She splashed to an impressive 4 ½-length win in the 1979 race, but looking back the Oaks was but one jewel in her crown. Davona Dale’s Kentucky Oaks score was her fourth victory in an eight-race win streak. She swept the Oaks, the Black-Eyed Susan Stakes at Pimlico Race Course and the Acorn Stakes at Belmont. She then completed the New York Triple Tiara by adding wins in the Mother Goose Stakes and the Coaching Club American Oaks to her Acorn victory. Davona Dale was named champion 3-year-old filly and has a Kentucky Oaks prep race named after her at Gulfstream Park.

Just one year after Rachel Alexandra’s dominant Oaks win, Blind Luck took the 2010 edition in another thriller. Sold for just $11,000 as a yearling, Blind Luck blossomed into one of the most determined racemares of recent years. She entered the Kentucky Oaks off a win in the Fantasy Stakes with a trio of Grade 1 (highest level) wins already to her credit, justifying her 1.30-1 favoritism. After starting the race in her customary last position, Blind Luck began to inhale her competition on the turn for home but was still in third near midstretch, digging deep and catching Evening Jewel just before the finish line in a head-bobbing finish. She was named that year’s champion 3-year-old filly.

The 2002 edition of the Kentucky Oaks gives the 1981 race a run for its money in terms of star power. Heavy favorite Take Charge Lady was run down late by 20-1 longshot Farda Amiga, with Habibti closing for third and You holding on for fourth. Imperial Gesture finished a disappointing eighth of nine after being slammed at the start. Now for the credentials: Farda Amiga was named champion that year after she won the historic Alabama Stakes and finished second to future Hall of Famer Azeri in the 2002 Breeders’ Cup Distaff. Take Charge Lady finished first or second in 18 of her 22 career races, including three Grade 1 wins at Keeneland, and later produced (became the mother of) champion Will Take Charge and Grade 1 winner Take Charge Indy, plus she is the grandam (maternal grandmother) of champion Take Charge Brandi. You was first, second or third in 19 of her 23 career races, including five Grade 1 wins. Habibti was a multiple Grade 1 winner at age 2, and Imperial Gesture later won a pair of Grade 1 races and finished third, just behind Farda Amiga, in the Breeders’ Cup Distaff. The 2002 Oaks gives “field of dreams” a whole new meaning!