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Keeneland’s Fall Stars Weekend packed with Breeders’ Cup prep races


The upcoming weekend of racing holds the final opportunities for horses aiming for an automatic berth in the Breeders’ Cup World Championships at Santa Anita Park on Nov. 1-2, as Keeneland, Belmont Park, and Santa Anita Park offer a total of 15 Challenge Series “Win and You’re In” qualifying races that provide a spot in the Breeders’ Cup starting gate for each winner.

Picturesque Keeneland in Lexington, Ky., hosts nine “Win and You’re In” races over its Fall Stars weekend, starting with the Grade 1 Darley Alcibiades Stakes and Grade 2 Stoll Keenon Ogden Phoenix Stakes on Friday. Those races offer automatic berths for the Breeders’ Cup Juvenile Fillies and the Breeders’ Cup Sprint, respectively. On Saturday, Keeneland runs the Grade 1 Shadwell Turf Mile Stakes (a prep for the TVG Breeders’ Cup Mile); the Grade 1 Claiborne Breeders’ Futurity (TVG Breeders’ Cup Juvenile); the Grade 1 First Lady Stakes (Maker’s Mark Breeders’ Cup Filly and Mare Turf); and the Grade 2 Thoroughbred Club of America Stakes (Breeders’ Cup Filly and Mare Sprint). And then on Sunday, Oct. 6, Keeneland features the Grade 1 Juddmonte Spinster Stakes (Longines Breeders’ Cup Distaff) the Grade 2 Dixiana Bourbon Stakes (Breeders’ Cup Juvenile Turf), and the Indian Summer Stakes (a qualifier for the Breeders’ Cup Juvenile Turf Sprint).

Four other Challenge Series races will be held at Belmont Park on Saturday and Sunday – Saturday’s Grade 1 Champagne Stakes (TVG Juvenile) and Sunday’s Grade 1 Frizette Stakes (Juvenile Fillies), Flower Bowl Stakes (Maker’s Mark Filly and Mare Turf), and Futurity Stakes (Breeders’ Cup Juvenile Turf Sprint). And Santa Anita Park holds both the Grade 1 Santa Anita Sprint Championship, a qualifier for the Sprint, and the Speakeasy Stakes, a qualifier for the Juvenile Turf Sprint, on Saturday. Those New York and California preps, as well as five “Win and You’re In” races held at Longchamp Racecourse in France on Sunday, are discussed in a separate article accessible here.

Television coverage of Saturday’s Claiborne Breeders’ Futurity and Shadwell Turf Mile will be featured on an NBC Sports broadcast on NBCSN from 5:30-6:30 p.m. ET. The Juddmonte Spinster Stakes and the Dixiana Bourbon Stakes, both on Sunday, will be broadcast on NBC from 4:30-6 p.m. All of Belmont Park’s “Win and You’re In” races will be broadcast on NYRA’s “America’s Day at the Races” show presented by Runhappy, Claiborne Farm, and America’s Best Racing, airing on FS2. All of the above preps as well as Santa Anita’s Challenge Series races and five Breeders’ Cup preps from Longchamp on Sunday will be broadcast by TVG as part of its comprehensive coverage. For more information, click here.

The 14 Breeders’ Cup races attract the best Thoroughbreds in the world to compete for $30 million in purse money and awards, and the selection of starters in each race is determined in part by a points system for graded stakes and the selection criteria of a panel of experts. However, there is one way for an owner to bypass the secondary criteria and secure a spot for their horse in a Breeders’ Cup race, and that is by winning a stakes race in the Breeders’ Cup Challenge Series.

Here’s some background on this weekend’s “Win and You’re In” qualifying races from Keeneland:

Shadwell Turf Mile Stakes

The Shadwell Turf Mile, sponsored by Sheikh Hamdan bin Rashid al Maktoum’s breeding and racing operation, was first held in 1986 and has had several name changes. It’s been a key prep for the Breeders’ Cup Mile — in recent years especially — and usually gives one last opportunity for top turf milers in North America to tune up for the World Championships. In 1989, English-bred Stenlein, owned by the late Daniel Wildenstein and trained by D. Wayne Lukas, became the first horse to win both races in the same year, and two years later, Allen Paulson’s Opening Verse ran second in the then-named Keeneland Breeders’ Cup Stakes before winning the Breeders’ Cup Mile as a 26.70-1 longshot. The horse that defeated Opening Verse at Keeneland, Itsallgreektome, finished second in that year’s Breeders’ Cup Turf after finishing second in the Mile the year before.

After Opening Verse’s 1991 win, there was a long gap where no Shadwell Turf Mile runner made any significant impression on the Breeders’ Cup Mile, although Quiet Resolve, third in the 2000 Shadwell Turf Mile, did finish a close second at long odds in that fall’s Breeders’ Cup Turf to Kalanisi. (Of note: Favorite Trick, discussed below, won the 1998 Turf Mile one year after his Horse of the Year campaign as he made his final two career starts on grass.) Finally, in 2003, Shadwell Turf Mile third-place finisher Touch of the Blues ran a very good second to Six Perfections in the Breeders’ Cup Mile. Three years later, Live Oak Plantation’s Miesque’s Approval followed up a fourth-place effort in the Shadwell Mile with a rousing four-length win in the Breeders’ Cup Mile at Churchill Downs at odds of 24.30-1.

Since Miesque’s Approval’s win, there’s been consistent crossover between the Shadwell Turf Mile and the Breeders’ Cup Mile. 2007 Shadwell runner-up Cosmonaut finished third in that year’s Mile, and 2009 Shadwell Turf Mile winner Court Vision ran in three consecutive editions of the Breeders’ Cup Mile starting in that same year. The hard-knocking Gulch horse checked in fourth and fifth before winning at gargantuan odds of 64.80-1 in 2011, defeating Turallure and Hall of Famer Goldikova.

Over the next several years, two superstars of the turf dominated at Keeneland and were constant presences at the Breeders’ Cup as well. Multiple champion Gio Ponti won back-to-back Shadwell Turf Miles in 2010 and 2011, and finished second and fourth, respectively, in the corresponding Breeders’ Cup Miles (he also finished second to Zenyatta in the 2009 Breeders’ Cup Classic). Wise Dan was beginning to emerge as a top-class turf horse by the second half of 2011, and in 2012 and 2013 he embarked on two consecutive Horse of the Year campaigns for owner Mort Fink and trainer Charles LoPresti. The Wiseman’s Ferry gelding won the 2012 Shadwell Turf Mile prior to defeating 2011 Kentucky Derby winner Animal Kingdom in the Breeders’ Cup Mile at Santa Anita. A year later, Wise Dan ran second to Silver Max in the Shadwell Mile, which was rained off of the turf and held on what was at the time Keeneland’s synthetic main track. He followed that effort up with a three-quarter-length score in the Breeders’ Cup Mile, again held at Santa Anita.

Wise Dan appeared in his third straight Shadwell Turf Mile in 2014 – the first race offering a $1 million purse in Keeneland history – and overcame a slow start to defeat Grand Arch by a length. Unfortunately, an ankle injury was detected after the race and Wise Dan missed the Breeders’ Cup Mile, won by longshot Karakontie. In fact, the ’14 Shadwell Turf Mile would be Wise Dan’s final career start, as he was retired by Fink in September 2015 with 23 wins in 31 starts and more than $7.5 million in earnings. Amazingly, Wise Dan won 19 of his final 22 starts dating back to summer 2011.

The 2015 Breeders’ Cup Mile was won by another popular champion, but of the distaff variety, in First Lady Stakes winner Tepin (see below). Grand Arch, winner of that year’s Shadwell Turf Mile, checked in third in the Breeders’ Cup event. In 2016, Shadwell Turf Mile third-place finisher Tourist closed out his career with a 12.40-1 upset win over Tepin in the Breeders’ Cup Mile (Shadwell winner Miss Temple City finished fifth). European invader Suedois won the Shadwell Turf Mile in 2017 and finished fourth in the Breeders’ Cup Mile at Del Mar, and last year Analyze it ran fourth in the Shadwell Turf Mile as the 2-1 favorite and then a very good third in the Breeders’ Cup Mile at Churchill Downs.

Juddmonte Spinster Stakes

The Juddmonte Spinster Stakes dates back to 1956 and has been sponsored by Khalid Abdullah’s Juddmonte Farms since 2005. The 1 1/8-mile race over Keeneland’s main track established an affiliation with the Breeders’ Cup Distaff at the outset, as Spinster winner Princess Rooney followed up a six-length romp at Keeneland with a seven-length blowout win over Life’s Magic in the inaugural World Championships at Hollywood Park. The 1984 Distaff was Princess Rooney’s career finale; she entered the Hall of Fame in 1991.

Life’s Magic, 1984’s champion 3-year-old filly, would win a second Eclipse Award as champion older female in 1985; the D. Wayne Lukas-trained filly finished second in the ’85 Spinster to Dontstop Themusic but ran away from that foe and runner-up Lady’s Secret in the Distaff to score by 6 ¼ lengths. Two years later, Sacahuista became the second filly to win both races in the same year when she romped in the Spinster by three lengths and in the Distaff by 2 ¼ lengths, leading at every point of call with Randy Romero aboard both times for Lukas.

Winning Colors, the last Kentucky Derby-winning filly to date in 1988, finished fourth in that fall’s Spinster and then second by a nose to Personal Ensign in a Distaff for the ages. And in both 1989 and 1990, future Hall of Famer Bayakoa used the Spinster as a springboard to the Distaff, winning all four renewals by a combined 22 ¾ lengths. Naturally, Janis and Frank Whitham’s racemare was voted champion older female at the Eclipse Awards for both campaigns.

Sid Craig’s Paseana became the next top-class filly to make her mark in both races in 1992 and 1993, finishing second to Fowda in the ’92 Spinster and then winning the Breeders’ Cup Distaff by four lengths under Chris McCarron. She would win the Spinster in ’93 and then come up a nose short of a Distaff repeat to Hollywood Wildcat. And in 1995, Inside Information became the fourth filly to achieve the Spinster-Distaff double, taking both races and the Eclipse Award for owner Ogden Phipps and trainer Shug McGaughey.

Three-year-old filly Banshee Breeze won the Spinster in 1998 but finished second by a nose to Escena in the Distaff; a year later, she would be runner-up in both races. Spain – the filly, not the country – came next in 2000, finishing a distant second to Plenty of Light in the Spinster but then rebounding to post a 55.90-1 upset in the Distaff. In 2001, Unbridled Elaine checked in fourth in the Spinster only to defeat Spain by a head in the Distaff for owner Roger Devenport and trainer Dallas Stewart. Take Charge Lady won back-to-back editions of the Spinster in 2002 and 2003 but underperformed in the Distaff.

In 2005, another Phipps-McGaughey filly, Pleasant Home, was runner-up in the Spinster but absolutely romped in the Distaff, winning by 9 ¼ lengths at odds of 30.75-1 under Cornelio Velasquez. 2006 Spinster winner Asi Siempre finished second in an injury-marred Distaff but was disqualified and placed fourth for interference. And in 2009, Mushka was elevated to first in the Spinster after being bothered by first-place finisher Proviso; she would then run second to Life Is Sweet in the Distaff.

During the late 2000s and early into this decade, there was a bit of a dip in the Juddmonte Spinster’s once-major influence as a Breeders’ Cup Distaff prep as Keeneland raced on a synthetic main track. Since Keeneland returned to dirt for the fall 2014 meet, the first four Juddmonte Spinster winners – Don’t Tell Sophia, Got Lucky, I’m a Chatterbox, and Romantic Vision – went on to finish second (to Untapable), 10th, fifth, and seventh in their respective Longines Breeders’ Cup Distaffs. On a brighter note, the sixth-place finisher in the 2017 Spinster, 1.90-1 favorite Bar of Gold, shortened up for her next – and as it turned out, final – start in the Breeders’ Cup Filly and Mare Sprint and pulled off a shocking 66.70-1 upset victory. Last year’s Spinster winner, Blue Prize, ran a decent fourth behind Monomoy Girl in the Longines Distaff and is listed as a probable starter for Sunday’s race.

Claiborne Breeders’ Futurity

The 1 1/16-mile Breeders’ Futurity has been sponsored by historic Claiborne Farm in Central Kentucky since 2014. Overall, the race has had a significant impact on the Sentient Jet Breeders’ Cup Juvenile, with four dual winners. The first came in 1985, the second year of the World Championships. West Coast-based Tasso shipped into Kentucky and competed twice at Keeneland during its fall meet, finishing second in a seven-furlong allowance before winning the Breeders’ Futurity by six lengths. One race later, the Neil Drysdale-trained son of Fappiano rallied strongly through the stretch under Laffit Pincay Jr. to edge future bloodstock legend Storm Cat by a nose in the Breeders’ Cup Juvenile at Aqueduct. Tasso raced for two more years but peaked as a 2-year-old, and was voted champion juvenile male at the Eclipse Awards.

Alysheba finished second in the 1986 Breeders’ Futurity and third in the Breeders’ Cup Juvenile before going onto much bigger and better things as a Kentucky Derby and Preakness winner in 1987 and Breeders’ Cup Classic winner in 1988. Over the next decade, a few horses moved on from Breeders’ Futurity wins to capture minor awards in the Juvenile, but it wasn’t until 1996 that another horse broke through with back-to-back wins in William T. Young’s Boston Harbor. That speedy D. Wayne Lukas-trained son of Capote lost only once in seven starts as a juvenile, and was an easy choice as champion 2-year-old male at the Eclipse Awards. He would race only once more at 3, however, and was retired due to injury.

One year after Boston Harbor’s championship season, Joseph LaCombe’s Favorite Trick went one better by winning the Breeders’ Futurity, the Breeders’ Cup Juvenile, the Eclipse Award as champion juvenile male, and Horse of the Year honors, too. All he did was go undefeated in 1997 through eight starts, taking three stakes at Churchill Downs and two at Saratoga (including the Grade 1 Hopeful) in addition to his back-to-back wins at Keeneland and in the Breeders’ Cup Juvenile at Hollywood Park. He would go on to have more success at age 3, winning the Jim Dandy and two other graded stakes, but will be remembered for his dominant campaign as a juvenile, one of the best debut seasons in recent racing history.

Cat Thief, eventual winner of the 1999 Breeder’s Cup Classic, took the Breeders’ Futurity at Keeneland the year before at 2 before finishing a close third in the Breeders’ Cup Juvenile. Things were quiet for a few years after that … until 2006, that is, when the top three finishers in the Breeders’ Futurity all hit the board again in the Breeders’ Cup Juvenile at Churchill Downs, albeit in a different order. At Keeneland, Doug O’Neill-trained California invader Great Hunter capitalized on a nice stalking trip to draw clear and win by 1 ¾ lengths over favored Circular Quay and Street Sense. That race was contested on Keeneland’s newly installed synthetic main track, however, and when the trio returned to dirt in the Breeders’ Cup Juvenile, it was Jim Tafel’s Street Sense who absolutely dominated the opposition, skipping through an inside opening at the top of the lane and winning by a widening 10 lengths under Calvin “Bo-rail,” with Circular Quay second and Great Hunter third. The Carl Nafzger trainee would earn Eclipse Award honors and then become the first Breeders’ Cup Juvenile winner to capture the Kentucky Derby in 2007.

Square Eddie, an easy winner of the 2008 Breeders’ Futurity on Keeneland’s synthetic main track, came home second to Midshipman in the Breeders’ Cup Juvenile at Santa Anita Park, which also had an artificial track at the time. A year later, still in the artificial-surface era, Breeders’ Futurity upset winner Noble’s Promise ran a game third in the Juvenile at Santa Anita. Jump ahead to 2012, and Breeders’ Futurity 11th-place finisher He’s Had Enough nearly scored a 19.60-1 upset in the Breeders’ Cup Juvenile, coming up a head short to Shanghai Bobby. Five years ago, Carpe Diem won the Claiborne Breeders’ Futurity and ran second to Texas Red in the Juvenile, and four years ago, Brody’s Cause took the Breeders’ Futurity and then checked in third in the Juvenile. In 2016, perhaps the best 2-year-old to appear in both races since Street Sense emerged on the scene, and John Oxley’s Classic Empire fittingly took home the Eclipse Award for his wins in the Breeders’ Futurity and Sentient Jet Breeders’ Cup Juvenile.

Last year produced a memorable Breeders’ Futurity-to-Breeders’ Cup Juvenile storyline, involving the longshot Knicks Go. The colt was ignored by bettors, exiting the starting gate at odds of 70-1, the highest in a 13-horse field. He proceeded to lead his competition around Keeneland’s oval without any serious challenge, and drew cries of disbelief (and a few of celebration) from the track’s jam-packed crowd as he drew clear to win by 5 ½ lengths. The win was the first Grade 1 for both young trainer Ben Colebrook and jockey Albin Jimenez.

That victory ensured that Knicks Go would receive more wagering attention in a loaded edition of the Breeders’ Cup Juvenile… and he did, but he still went off at odds of 40.50-1. Jimenez moved his colt up from an outside post to contest the pace through Churchill Downs’ backstretch, and Knicks Go briefly took the lead coming out of the far turn only to yield to eventual champion Game Winner in a runner-up effort that certainly validated his win at Keeneland, if nothing else.

Darley Alcibiades Stakes

The Alcibiades Stakes is the female counterpart to the Claiborne Breeders’ Futurity and has been sponsored by the breeding arm of Sheikh Mohammed bin Rashid al Maktoum’s worldwide Thoroughbred conglomerate since 2003. The first filly to come out of the Alcibiades and win the Breeders’ Cup Juvenile Filllies was Epitome in 1987. Runner-up to Terra Incognita at Keeneland, Epitome then won the Pocahontas Stakes at Churchill before scoring a 30.40-1 upset win by a nose over Jeanne Jones in the Juvenile Fillies at Hollywood Park, which was held in late November.

Three years later, Alcibiades winner Private Treasure was a distant second to champion filly Meadow Star in the Juvenile Fillies, and then in 1992, Allen Paulson’s Eliza became the first filly to win both races. The daughter of Mt Livermore romped by four lengths in the Alcibiades and was only slightly less impressive in the Juvenile Fillies, scoring by a length over Educated Risk.

Cara Rafaela almost accomplished the same feat in 1995, winning the Alcibiades but losing by a half-length to My Flag in the Juvenile Fillies at Belmont Park. She would eventually become an accomplished broodmare as the dam of champion and classic winner Bernardini. In 1997, another filly emerged to win both marquee races in Countess Diana. Owned by breeder Richard Kaster along with his wife, sister, and brother-in-law, Countess Diana dominated both at Keeneland and at Hollywood Park in the Breeders’ Cup, winning the events by a total of 11 ¼ lengths. She was trained as a juvenile by Patrick Byrne, who also trained the aforementioned Favorite Trick in 1997.

One year later, Silverbulletday became the third filly to win both the Alcibiades and Breeders’ Cup Juvenile Fillies. The Michael Pegram-owned, Bob Baffert-trained filly would retain her elite form through her 3-year-old season as well, winning the Kentucky Oaks among other races and receiving an additional Eclipse Award as top sophomore female to accompany her juvenile hardware. Silverbulletday entered the Racing Hall of Fame in 2009.

Cash Run, third in the 1999 Alcibiades, scored a 32.50-1 upset win in the Breeders’ Cup Juvenile Fillies, and in 2000 the fifth-place finisher and winner of the Alcibiades, Platinum Tiara and She’s a Devil Due, respectively, ran 2-3 in the Juvenile Fillies behind champion Caressing. Minor Breeders’ Cup awards at best were in order for the next several fillies who ran in both races, with the best showing coming in 2008, when Darley Alcibiades winner Dream Empress finished second to Stardom Bound in the Juvenile Fillies. One year later, however, another Alcibiades runner-up, She Be Wild, broke through to win the Juvenile Fillies. The Wayne Catalano trainee rallied along the rail under Julien Leparoux to win the Juvenile Fillies by three-quarters of a length at Santa Anita during the span when both Keeneland and “The Great Race Place” operated artificial surface main tracks.

Stephanie’s Kitten, winner of the 2011 Alcibiades, targeted the Breeders’ Cup Juvenile Fillies Turf instead of the main-track event at Churchill Downs, and won that race impressively in the early stages of an incredible career. In 2013, Darley Alcibiades runner-up Rosalind finished third in the Breeders’ Cup, a dual result also achieved by Dothraki Queen in 2015. Between those two renewals, in one of the more improbable Breeders’ Cup results, eighth-place 2014 Darley Alcibiades finisher Take Charge Brandi wired the field at odds of 61.70-1 in the 14 Hands Winery Juvenile Fillies, defeating Alcibiades runner-up Top Decile by a half-length.

Last year, Ken McPeek-trained Restless Rider won the Alcibiades by 1 ½ lengths as the 13-10 favorite, and then ran second behind dominant winner Jaywalk in the Juvenile Fillies at Churchill Downs.

First Lady Stakes

The one-mile First Lady Stakes was first held in 1998, one year before the inaugural Breeders’ Cup Filly and Mare Turf. It didn’t take long for the race to emerge as a key prep for the World Championships, as 2000 winner Tout Charmont and runner-up Perfect Sting reversed positions three weeks later in the Breeders’ Cup Filly and Mare Turf at Churchill Downs. Perfect Sting’s loss in what was then called the WinStar Galaxy Stakes was her only defeat in six starts that year, and she received the Eclipse Award as champion turf female.

A year later, Galaxy winner Spook Express was second to Banks Hill in the Filly and Mare Turf. Move ahead four years and Juddmonte Farms’ Intercontinental became the first filly to win both races in the same year. The Bobby Frankel-trained daughter of Danehill, from an elite female family that also included Banks Hill, defeated Wend in the Galaxy and then scored a 15.10-1 pacesetting upset victory in the Filly and Mare Turf at Belmont Park over international superstar and 2004 and 2006 Filly and Mare Turf winner Ouija Board. Needless to say, those wins were enough to earn Intercontinental an Eclipse Award in 2005.

Jump ahead to 2008, and George Stawbridge’s Forever Together became the second First Lady-Breeders’ Cup Filly and Mare Turf winner. The striking gray racemare also finished third in both races a year later. Chad Brown-trained Dayatthespa, runner-up to Better Lucky in the 2013 First Lady Stakes, returned to take the 2014 First Lady by 1 ¼ lengths over that foe and then won the Filly and Mare Turf in front-running fashion. The great champion Tepin rolled to a seven-length score in the 2015 First Lady, and then came back to Keeneland to face males in the Breeders’ Cup Mile, which she won by 2 ¼ lengths. Tepin was upset in the 2016 First Lady by runaway 29.70-1 winner Photo Call, but she returned in the Breeders’ Cup Mile to just miss a repeat score, losing to Tourist (noted above).

Last year’s First Lady winner, A Raving Beauty, finished third behind Chad Brown-conditioned stablemate Sistercharlie in the Maker’s Mark Filly and Mare Turf.

Stoll Keenon Ogden Phoenix Stakes

The Phoenix Stakes is the oldest recognized race in North America and dates back to 1831. Sponsored by a Kentucky law firm since 2011, the six-furlong test had little crossover with the Breeders’ Cup Sprint through the first 25 years or so since the World Championships began, with an exception being Bet On Sunshine (won the Phoenix in 1997 and third in the Sprint, and then third in both races in 2000). An interesting note: Wise Dan won the Phoenix in 2010 and finished sixth in the Sprint at Churchill Downs, several months before he was moved to turf and became a legend.

The Phoenix Stakes was added as a Challenge Series “Win and You’re In” race in 2012, and since then its status as a prep has risen significantly. Laugh Track, runner-up to Sum of the Parts in the 2013 Phoenix, nearly won the Sprint at Santa Anita, losing to Secret Circle by a neck. Then, in the next two years, Phoenix Stakes winners Work All Week and Runhappy each captured the Breeders’ Cup Sprint – Work All Week in 19.10-1 upset, Runhappy as the 8-5 favorite. Both were honored as champion sprinter at the year-end Eclipse Awards.

In 2016, Stoll Keenan Ogden Phoenix winner A. P. Indian finished fourth in the TwinSpires Sprint and was elevated to third after Masochistic was disqualified from second. The 2017 Phoenix winner, Whitmore, finished eighth in the Sprint and then returned to run second in both the 2018 Phoenix and the 2018 Breeders’ Cup Sprint. He is listed as probable for Friday’s renewal, as is 2018 Phoenix winner Promises Fulfilled, who defeated Whitmore by a head in last year’s Phoenix and subsequently ran fourth in the Sprint.

Thoroughbred Club of America Stakes

First held in 1981, the Thoroughbred Club of America Stakes sent winner Informed Decision on to score in the Breeders’ Cup Filly and Mare Sprint in 2009, the third year of the latter race’s existence. George Strawbridge’s filly was a synthetic-track specialist, and won in driving fashion both at Keeneland and Santa Anita, which had artificial main tracks at the time. A year later, former claimer Dubai Majesty became the second straight filly to take both races, winning by three-quarters of a length at Keeneland and then running her career-best race in the Filly and Mare Sprint at Churchill Downs to prevail by an impressive 2 ¼ lengths with Jamie Theriot aboard (Informed Decision, third in the 2010 Phoenix, finished seventh in the Filly and Mare Sprint). That championship-sealing win was Dubai Majesty’s 34th and final career start.

The connection between the Thoroughbred Club of America Stakes and the Breeders’ Cup Filly and Mare Sprint has remained very strong. In 2011, TCA runner-up Musical Romance and third-place Switch ran 1-2 in the Filly and Mare Sprint, again at Churchill Downs (Switch also finished second to Dubai Majesty at Churchill the year before and third in the 2012 Filly and Mare Sprint). And in ’12, the beloved Groupie Doll became the third filly in four years to win both races. The pride of Frankfort, Ky., came back in 2013 to win another Breeders’ Cup Filly and Mare Sprint for trainer Buff Bradley, defeating Judy the Beauty, who had upset Groupie Doll in the TCA one race prior. Groupie Doll would race twice more before retiring in early 2014; meanwhile, Judy the Beauty would train on and defeat First Lady Stakes runner-up Better Lucky by a head to claim her own Filly and Mare Sprint that fall at Santa Anita.

Last year’s TCA winner, Golden Mischief, finished fifth in the Breeders’ Cup Filly and Mare Sprint, while runner-up Chalon again finished second in the Filly and Mare Sprint, losing to longshot Shamrock Rose by a head in a blanket finish.

Dixiana Bourbon Stakes

The Bourbon Stakes, first held in 1991 and sponsored by Lexington’s Dixiana Farms since 2014, has sent a few winners on to perform respectably in the Breeders’ Cup Juvenile Turf, but as of yet none has won. The best showing came in 2015, when sharp Dixiana Bourbon winner Airoforce nearly took the Juvenile Turf right back at Keeneland, only to lose by a neck to Irish invader Hit It a Bomb as both closed with a rush.

Indian Summer Stakes

Last year, Chelsea Cloisters ran second by a neck to Strike Silver in a thrilling inaugural edition of the Indian Summer Stakes, and then backed that up with another runner-up finish – to dominant winner Bulletin – in the inaugural Juvenile Turf Sprint at Churchill Downs (Strike Silver finished seventh).

Oct. 9: JPMorgan Chase Jessamine Stakes

On Wednesday, Oct. 9, the final “Win and You’re In” race will be held at Keeneland. The JPMorgan Chase Jessamine Stakes offers the winner an automatic berth in the Breeders’ Cup Juvenile Fillies Turf, and 2008 winner Laragh finished a close third in the first-ever running of that Breeders’ Cup race at Santa Anita Park. House of Grace achieved the same results in each race a year later, and believe it or not, Kathmanblu did the same thing in 2010 with a first in Jessamine-third in Breeders’ Cup combo. Over the next several years, most of the top finishers in the Jessamine contested the World Championships, a few of them running well without winning ... but that fruitless streak ended in 2017.

Rushing Fall took the JPMorgan Chase Jessamine by a dominant 3 ¼ lengths for owner e Five Racing Thoroughbreds and trainer Chad Brown and then shipped to Del Mar and won the Juvenile Fillies Turf by three-quarters of a length over Best Performance. The filly has remained in top form over the past year and a half, winning five more graded stakes, including three Grade 1s.

Last year’s Jessamine winner, Concrete Rose, finished eighth in the Juvenile Fillies Turf but won her first four races of 2019 – including the first two legs of NYRA’s new Turf Tiara – before being sidelined for the rest of the year due to injury.

Of note: The Oct. 5 Grade 3 Woodford Stakes Presented by Keeneland Select is not a “Win and You’re In” qualifier for the Breeders’ Cup Turf Sprint, but a few notables have come out of the 5 ½-furlong dash on Keeneland’s bluegrass and gone on to greater glory in the’ Turf Sprint since the latter race began in 2008. Most notably, Chamberlain Bridge exited a fourth-place finish in the Woodford to win the Turf Sprint at Churchill Downs in 2010, and a year later, Woodford 2-3 finishers Perfect Officer and Country Day finished 3-2 a race later at Churchill Downs in the Turf Sprint behind Regally Ready. In 2014, Wesley Ward-trained No Nay Never won the Woodford and then finished a half-length behind Bobby’s Kitten in an absolutely thrilling Turf Sprint at Santa Anita. And a year later, Mongolian Saturday lost the Woodford by a half-length to longshot Amelia’s Wild Ride but wheeled back to Keeneland and won the 2015 Breeders’ Cup Turf Sprint for his East Asian connections. Mongolian Saturday came back to win the 2016 Woodford as well. Bucchero won back-to-back editions of the Woodford in 2017 and 2018 and also competed in the Breeders’ Cup Turf Sprint in both years, finishing fourth (beaten a length) in 2017 and eighth in 2018.

The Breeders’ Cup Challenge Series continues on NBC Sports with Fall Stars Weekend from Keeneland on October 5 at 5:30 p.m. ET on NBCSN and October 6 at 4:30 p.m. ET on NBC.