Road to the 2021 Breeders' Cup: All Eyes on Keeneland For Fall Stars Weekend

Essential Quality won the 2020 Breeders’ Futurity at Keeneland one race prior to capturing the Breeders’ Cup Juvenile at the same track, which propelled him to earn champion 2-year-old male honors at the Eclipse Awards. (Eclipse Sportswire)

The upcoming weekend of racing is a very crucial one for owners of horses that are seeking an automatic berth in the Breeders’ Cup World Championships at Del Mar a little more than five weeks from now. The bulk of the action will take place in the heart of horse country, as Keeneland Race Course in Lexington, Ky., offers a total of nine Challenge Series “Win and You’re In” preps for during its kickoff Fall Stars Weekend, with an additional one slated for Oct. 13. 

The top-class racing, as indicated by Keeneland's clever marketing, lasts all weekend long, 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, the track runs the Grade 1 Keeneland Turf Mile Stakes (a prep for the FanDuel Breeders’ Cup Mile Presented by PDJF); the Grade 1 Claiborne Breeders’ Futurity (TVG Breeders’ Cup Juvenile Presented by Thoroughbred Aftercare Alliance); the Grade 1 First Lady Stakes Presented by UK Healthcare (Maker's Mark Breeders’ Cup Filly and Mare Turf); and the Grade 2 Thoroughbred Club of America Stakes (Breeders’ Cup Filly and Mare Sprint). On Sunday, Keeneland features the Grade 1 Juddmonte Spinster Stakes (Longines Breeders’ Cup Distaff), the Grade 2 Castle & Key Bourbon Stakes (Breeders’ Cup Juvenile Turf), and the Indian Summer Stakes Presented by Keeneland Select (a qualifier for the Breeders' Cup Juvenile Turf Sprint). The final race in the Breeders’ Cup Challenge Series will be held at Keeneland on Wednesday, Oct. 13. The Grade 2 JPMorgan Chase Jessamine Stakes offers a fees-paid berth to the Breeders’ Cup Juvenile Fillies Turf.

Two more domestic “Win and You’re In” preps will be held at Belmont Park: the Grade 2 Vosburgh Stakes, a Challenge Series qualifier for the Breeders’ Cup Sprint on Saturday, and the Grade 3 Futurity Stakes on Sunday, a qualifier for the Breeders’ Cup Juvenile Turf Sprint.

Television coverage of Friday's two Breeders' Cup preps at Keeneland will be featured on an NBC Sports broadcast on NBCSN starting at 5 p.m. ET, and NBCSN will also show three preps – the Breeders’ Futurity, the Keeneland Turf Mile, and the First Lady – on a Saturday program beginning at 5 p.m. The Juddmonte Spinster Stakes and the Dixiana Bourbon Stakes, both on Sunday, will be broadcast on NBCSN starting at 4:30 p.m. Lastly, the Jessamine will air on NBCSN Wednesday on a show starting at 4 p.m. ET.

Racing from Belmont Park will be shown live on NYRA's "America's Day at the Races" program from Thursday to Sunday, airing on FS2 and FS1. Racing at Keeneland, Santa Anita Park, and other tracks will also be shown on TVG as part of its comprehensive coverage. 

The 14 Breeders’ Cup races attract the best Thoroughbreds in the world to compete for $31 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:

Keeneland Turf Mile Stakes

This race was first held in 1986 and has had several name changes and sponsors; it was sponsored by Shadwell Farm from 1999 to 2020 but is designated the Keeneland Turf Mile for this year’s renewal. 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 Park. 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 in 2018 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. Brazilian-bred Ivar, upset winner of last year’s Turf Mile at Keeneland, came right back to the turf course and ran a solid fourth in the Breeders’ Cup Mile.

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 on 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 ran 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.

Inside Information wins the 1995 Breeders' Cup Distaff. (BloodHorse/Skip Dickstein photo)

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 Breeders’ Cup Ladies Classic, as the Distaff was known at the time.

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.

The 2018 Spinster winner, Blue Prize, ran a decent fourth behind Monomoy Girl in the Longines Distaff at Churchill Downs, and then returned to Keeneland in October 2019 and scored a repeat victory in the Spinster over odds-on favorite Elate. Blue Prize targeted the Longines Distaff again, shipping to Santa Anita Park for trainer Ignacio Correas. Sent off at odds of 8.90-1, the Argentine-bred pulled off another upset, this time over even-money favorite Midnight Bisou, and closed her career with a 1 ½-length victory. She subsequently was sold for $5 million as a broodmare prospect at the Fasig-Tipton November sale just days after her Breeders’ Cup triumph.

Last year, Todd Pletcher-trained Valiance rallied in the stretch to edge Ollie’s Candy by a half-length, scoring a mild upset in the Spinster at 6.40-1 odds. The striking gray filly came back in a loaded Distaff at Keeneland and validated her run from five weeks earlier, coming from off the pace again and finishing a clear second to future Hall of Famer Monomoy Girl, who won her second Distaff. That turned out to be Valiance’s final start – she was recently retired after not racing this year and will be offered as a broodmare prospect at the Fasig-Tipton November sale.

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 Breeders’ Cup Juvenile, with five 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.

Favorite Trick (Skip Dickstein/BloodHorse)

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. In 2014, Carpe Diem won the Claiborne Breeders’ Futurity and ran second to Texas Red in the Juvenile, and in 2015, Brody’s Cause took the Breeders’ Futurity and then checked in third in the Juvenile behind eventual Kentucky Derby winner Nyquist. 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.

2018 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.

Following the Juvenile, Knicks Go continued to race but his form declined and he lost all eight of his starts at age 3 in 2019. Sent to trainer Brad Cox for his 4-year-old season in 2020, he bounced back to emerge as one of the top older horses in training – and he has maintained that status at age 5 this year, dominating several prestigious races and establishing himself as a leading win candidate in next month’s Longines Breeders’ Cup Classic.

Speaking of Cox, the Louisville native steered a promising son of Tapit to the Breeders’ Futurity last year off of a debut win at Churchill Downs, and Godolphin’s Essential Quality delivered a rousing 3 ¼-length victory in front of a COVID-19 impacted, near-empty grandstand on Fall Stars Saturday with Luis Saez riding. Sent off as the second betting choice in the TVG Juvenile at Keeneland, he swept into contention out of the far turn and outfinished a 94.40-1 longshot named Hot Rod Charlie for a three-quarter-length victory. As the fifth horse to pull off the Breeders’ Futurity-Breeders’ Cup Juvenile double, Essential Quality was an easy choice for the Eclipse Award as champion 2-year-old male of 2020. All he’s done since then is win five of six starts, including the Belmont Stakes Presented by NYRA Bets and the Runhappy Travers Stakes, to join stablemate Knicks Go (and Hot Rod Charlie, for that matter) as prime threats in the 2021 Longines Classic.

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, classic winner and sire 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.

Silverbulletday winning the 1999 Kentucky Oaks. (Anne Eberhardt/Blood-Horse)

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.

In 2018, 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. And in 2019, British Idiom became the fourth filly to win both the Alcibiades and the Juvenile Fillies, romping at Keeneland by 6 ½ lengths and then edging Donna Veloce by a neck at Santa Anita. The Brad Cox trainee won the Eclipse Award as champion 2-year-old filly. Last year’s Alcibiades winner, Simply Ravishing, finished fourth back at Keeneland in the Juvenile Fillies.

First Lady Stakes Presented by UK Healthcare

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.

Tepin (Eclipse Sportswire)

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).

The 2018 First Lady winner, A Raving Beauty, finished third behind Chad Brown-conditioned stablemate Sistercharlie in the Maker’s Mark Filly and Mare Turf. And another Brown trainee, Uni, capped off a championship year in 2019 with back-to-back wins in the First Lady and the Breeders’ Cup Mile, skipping the Filly and Mare Turf and competing at the shorter mile distance at Santa Anita. Uni came back to win the First Lady again last year but could not pull off the First Lady-Breeders’ Cup Mile double again, finishing fifth in the World Championships event to European longshot Order of Australia in her final career start.

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 ... and then second again in the Phoenix and third in the Sprint in 2019. The indefatigable fan favorite came back for more last year and finished fourth in the Phoenix. Trainer Ron Moquett kept him at Keeneland for the Breeders’ Cup Sprint, and Whitmore was sent off at odds of 18.40-1 in a wide-open race. Under jockey Irad Ortiz Jr., Whitmore saved ground through the turn and picked off horses in the stretch en route to a benchmark 3 ¼-length score in the Sprint. The 7-year-old received the Eclipse Award as champion sprinter and came back for another season at 8 this year but was recently retired with absolutely nothing left to prove after suffering an injury.

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 TCA, 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 finisher 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.

The 2018 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. The 2019 TCA victress Spiced Perfection finished fourth behind champion Covfefe, while TCA runner-up Dawn the Destroyer checked in third at Santa Anita.

Castle & Key Bourbon Stakes

The Bourbon Stakes, first held in 1991, 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. In 2019, Gear Jockey finished third in both races, and interestingly, eventual dirt Grade 1 winner Art Collector finished seventh in the Bourbon. Both Gear Jockey and Art Collector have matured to become viable Breeders’ Cup contenders in 2021, pointing to the Turf Sprint and the Longines Classic, respectively.

Indian Summer Stakes Presented by Keeneland Select

In 2018, 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). Two years ago, Kimari defeated Chimney Rock in the Indian Summer; the latter horse subsequently finished second to Four Wheel Drive in the 2019 Juvenile Turf Sprint, while Kimari finished fourth. Last year’s Indian Summer runner-up Cowan repeated that effort five weeks later in the Juvenile Turf Sprint; the Steve Asmussen trainee spent part of this year racing overseas but resurfaced at Churchill Downs in September with a game win on dirt.

Vosburgh Stakes

The historic Vosburgh Stakes was run at seven furlongs during the Breeders’ Cup era until 2004, when it was held at 6 ½ furlongs for one year before being shortened to its current six furlongs in 2005. Groovy, winner of the 1987 Vosburgh, became the first horse from the race to perform well in the Breeders’ Cup Sprint when he ran second, albeit by four lengths, to Very Subtle. The Texas-bred was a 4-5 favorite in the Breeders’ Cup, which was his first loss of the year after winning seven in a row. He was honored with an Eclipse Award as champion sprinter for his body of work.

One year later, the situation reversed as Vosburgh runner-up Gulch rallied late to take the Breeders’ Cup Sprint by three-quarters of a length under Angel Cordero Jr. The D. Wayne Lukas trainee won the Eclipse Award for his division and had some success at stud as well, siring 1995 Kentucky Derby and Belmont Stakes winner Thunder Gulch among others. In 1989, Ogden Phipps’ Dancing Spree finished fourth in the Vosburgh only to post a 16.60-1 upset win in the Breeders’ Cup Sprint. That gave Angel Cordero Jr. back-to-back wins in the Sprint; the Hall of Famer had previously finished second in 1986 and 1987 (aboard Groovy).

Jump into the 1990s, and another Vosburgh also-ran, Cherokee Run, achieved peak form in the 1994 Breeders’ Cup en route to championship honors. That Florida-bred son of Runaway Groom could not hold his lead in the Vosburgh, surrendering late to finish third, but then turned it around one race later with Mike Smith in the irons, rallying to post a head win over Soviet Problem in the Breeders’ Cup Sprint at Churchill Downs.

Artax, the first horse to win both the Vosburgh and the Breeders’ Cup Sprint in the same year, did so in 1999 when he defeated Kona Gold (subsequent winner of the 2000 Sprint) by a half-length. His wins bookended a score in the Forest Hills Handicap and were enough to garner an Eclipse Award.

Crossover success between the Vosburgh and Breeders’ Cup Sprint continued into the 2000s, as Bobby Frankel-trained Squirtle Squirt, second to Left Bank in the 2001 Vosburgh, returned to Belmont Park in the Sprint and defeated Xtra Heat by a half-length under a well-timed ride by Jerry Bailey. The Vosburgh winner in 2003 was another Bobby Frankel trainee, who took the only renewal of the race at 6 ½ furlongs to pick up his first career stakes win. That horse did not go on to the ’03 Breeders’ Cup. Instead, he came back to dominate in 2004 and score an overpowering win in the Breeders’ Cup Classic. The name: Ghostzapper.

Speightstown, third in the 2004 Vosburgh, impressively won the Breeders’ Cup Sprint at Lone Star Park shortly before Ghostzapper’s win in the Classic. A year later, Vosburgh winner Taste of Paradise came up just a head short to Silver Train in the Sprint. And more recently, horses such as Force Freeze (second in the 2011 Vosburgh and Breeders’ Cup Sprint); The Lumber Guy (won the 2012 Vosburgh, second in the Sprint); and Private Zone (won the 2013 and 2014 Vosburghs, third in the 2014 Sprint and second in the 2015 Sprint) have put up good showings in both events.

Three years ago, 2017 Breeders’ Cup Sprint runner-up Imperial Hint won the 2018 Vosburgh by 1 ½ lengths as the 1-5 favorite and then finished third in the 2018 Sprint at Churchill Downs as Roy H notched a repeat win. The “little rocket,” as so named by trainer Luis Carvajal Jr., came back to win the Vosburgh again in 2019 by a nose over Firenze Fire but missed a third try at the Breeders' Cup Sprint with a minor injury. He was retired in May 2020.

After losing the 2019 Vosburgh and finishing fifth in the Sprint, Firenze Fire won last year’s Vosburgh to improve his career record at Belmont Park to five wins in eight starts. He finished a late-running third behind the above-discussed Whitmore in the 2020 Breeders’ Cup Sprint and has come back as good as ever in 2021, tallying two more wins at Belmont – both in graded stakes – and gaining national notoriety in his most recent start by biting his rival Yaupon (the racetrack term is “savaging”) during the stretch of the Forego Stakes at Saratoga. Firenze Fire is pointed toward his third consecutive start in the Vosburgh Saturday.

Futurity Stakes

The Futurity Stakes at Belmont was added to the “Win and You’re In” Challenge Series schedule in 2018. Uncle Benny, winner of the 2018 Futurity Stakes, actually did not compete in the Breeders’ Cup Juvenile Turf Sprint but instead started in the 1 1/16-mile Juvenile Turf at Churchill Downs, where he ran a valiant second to European invader Line of Duty, losing by a half-length and being bumped by that foe in deep stretch.

In 2019, Wesley Ward-trained Four Wheel Drive became the first horse to sweep the Futurity-Juvenile Turf Sprint double, winning at Belmont by three lengths and at Santa Anita by three-quarters of a length.

JPMorganChase Jessamine Stakes

Rushing Fall (Eclipse Sportswire)

Keeneland's JPMorgan Chase Jessamine Stakes offers the winner an automatic berth in the Juvenile Fillies Turf, and 2008 Jessamine 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. Rushing Fall remained in elite form since then, winning eight more graded stakes, including five Grade 1s. She concluded her career in last year's Breeders’ Cup Filly and Mare Turf with a runner-up effort behind European filly Audarya, beaten by a neck; overall, Rushing Fall won a staggering five graded stakes at Keeneland, second only to Wise Dan's seven graded stakes in the storied track's history.

The 2019 Jessamine winner, Sweet Melania, checked in third in the Juvenile Fillies Turf behind Sharing. And last year, Aunt Pearl became the second filly to win both races in the same year. The Irish-bred Lope de Vega filly, a pure front-runner, gave Brad Cox the first of what turned out to be four wins during the two-day World Championships at Keeneland with an easy 2 ½-length win over Coolmore invader Mother Earth; that win followed up a similarly impressive victory in the Jessamine by the same margin.

Of note:

The Grade 2, 1 1/8-mile Beldame Stakes at Belmont on Sunday is not a Challenge Series “Win and You’re In” qualifier for the Longines Breeders’ Cup Distaff, but its history is deeply intertwined with the top World Championships dirt race for females, starting back in 1984 when Beldame winner Life’s Magic finished second in the inaugural Distaff. Life’s Magic would win the 1985 Distaff over 3-year-old Lady’s Secret (see above), who had taken the Beldame by an easy two lengths and entered the Breeders’ Cup on an eight-race winning streak. It was no contest in the Distaff at Aqueduct, as Angel Cordero Jr. piloted Life’s Magic to a 6 ¼-length win. A year later, Lady’s Secret would win both the Beldame and Breeders’ Cup Distaff to secure Horse of the Year honors. The “Iron Lady” would enter the Hall of Fame in 1992.

Another Reagan-era superstar, Personal Ensign, won the Beldame and the Breeders’ Cup Distaff in 1988, the latter by a hard-earned nose over Winning Colors (see above). Heavenly Prize won the 1994 Beldame and finished second in the Distaff, and a year later ran second in both events. Serena’s Song won the 1995 Beldame over Heavenly Prize and would finish runner-up to Jewel Princess in the 1996 Distaff en route to Hall of Fame induction in 2002. Ajina was second best in the 1997 Beldame but won the Distaff by two lengths for Allen Paulson and Bill Mott. And in 1999, John Oxley’s Beautiful Pleasure became the fourth filly to win both events in the same calendar year, defeating Silverbulletday in the Beldame and Banshee Breeze in the Distaff.

Royal Delta (Eclipse Sportswire)

Nearly every year it seems, the Beldame has continued to be a significant prep for the Breeders’ Cup Distaff. 2001 Beldame third-place finisher Spain nearly won the Distaff three weeks later at Belmont Park, yielding to Unbridled Elaine at the finish line. Ginger Punch, third in the 2007 Beldame, rebounded to post a game neck win in the Distaff for Frank Stronach and Bobby Frankel; she would later finish second in the 2008 Beldame. Three years on, Beldame runner-up Unrivaled Belle won the Distaff (then called the Ladies’ Classic) at odds of 7.50-1 in a race that will always be remembered for the actions of Beldame winner Life At Ten, who refused to compete.

Royal Delta, runner-up to Havre de Grace in the 2011 Beldame, won the Ladies’ Classic as a 3-year-old. A year later, the Besilu Stables star won both races – romping in the Beldame by 9 ½ lengths – and secured her second consecutive Eclipse Award. She would finish second to Princess of Sylmar in the 2013 Beldame and then fourth in the Distaff, but receive another championship trophy anyway.  

Stopchargingmaria finished a well-beaten second in the 2014 Beldame but a year later won the Longines Distaff at Keeneland. And in 2016, Forever Unbridled won the Beldame impressively before running a solid third behind superstars Beholder and Songbird in the Longines Distaff. The Dallas Stewart-trained racemare returned in 2017 to win the Longines Distaff (Beldame winner Elate was fourth) and earn champion older dirt female honors at the Eclipse Awards.

In 2018, Chilean import Wow Cat won the Beldame in her third start in North America and then ran a very good second behind champion Monomoy Girl in her next start, the Distaff at Churchill Downs. Wow Cat finished a well-beaten second to odds-on Midnight Bisou in the 2019 Beldame; the winner entered the Longines Distaff a perfect 7-for-7 in 2019 but saw that streak end at even-money odds when she finished runner-up to the above-discussed Blue Prize. Midnight Bisou still earned the Eclipse Award as champion older dirt female of 2019.  

Dunbar Road, third in last year’s Beldame, also ran on late to nab third behind Monomoy Girl and Valiance in the Longines Distaff at Keeneland.

Saturday's 1 ½-mile, Grade 1 Joe Hirsch Classic Stakes at Belmont, named after the legendary New York turf writer, is also not a "Win and You're In" race for 2021, but it has been arguably the most important domestic prep race for the Longines Breeders’ Cup Turf since the World Championships began in 1984. Strawberry Road, third in the 1985 renewal, ran second by a neck to Pebbles six weeks later in the second Breeders’ Cup Turf, but that was only the beginning. The next year, powerhouse Manila, a 2008 inductee into the Racing Hall of Fame, posted consecutive wins in the Joe Hirsch (then named just the Turf Classic) and the Breeders’ Cup Turf, edging Theatrical by a neck in the latter event. Theatrical, another one of the sport’s 1980s-era turf stars, won both races in 1987, with a victory in the Man o’ War Stakes sandwiched in between. And another year on, Darby Dan Farm’s Sunshine Forever almost made it a three-peat for sweeping both races, dominating in the Turf Classic and coming a half-length shy of longshot Great Communicator in the Breeders’ Cup Turf at Churchill Downs.

1990 Turf Classic third-place finisher With Approval, voted Horse of the Year in his native Canada one year prior, ran second to In the Wings in that fall’s Breeders’ Cup Turf. And in 1992, the order of finish at Belmont in the Turf Classic, won by Sky Classic over Fraise, was reversed in the Breeders’ Cup Turf at Gulfstream Park, with Fraise prevailing by a nose. Two years later, Tikkanen, owned and bred by George Strawbridge, made his first start in the U.S. in the 1994 Turf Invitational and won in an upset over Vaudeville. He then pulled off another long-odds win in the Breeders’ Cup Turf at Churchill, defeating the filly Hatoof by 1 ½ lengths at 16.60-1. 

After a decade of dominance, the Turf Classic did not have much of an influence on the Breeders’ Cup Turf for a few years, until 1998, when Buck’s Boy became the fourth horse two win both races in the same year. Bred in Illinois and racing primarily in that state and in Florida early in his career, Buck’s Boy gradually rose to the top of his class, finishing fourth in the 1997 Breeders’ Cup Turf and third in 1999 in addition to his wire-to-wire win in 1998. He received the Eclipse Award for champion turf male in 1998.

As the 1990s ended and a new century began, several Turf Classic Invitational winners continued to perform well in the Breeders’ Cup, most notably 2004’s Kitten’s Joy, who took the Turf Classic Invitational with ease before losing to Better Talk Now in an upset in the Breeders’ Cup Turf at Lone Star Park. Kitten’s Joy would be crowned champion turf male at the Eclipse Awards; today’s he’s one of North America’s leading sires.

The next three years were dominated by English Channel, who finished second in the newly-named Joe Hirsch Turf Classic Invitational in 2005 and then won the next two renewals by a combined 6 ¾ lengths. The Smart Strike horse, a star for owner James Scatuorchio and trainer Todd Pletcher, ran fifth in the ’05 Breeders’ Cup Turf, third in 2006, and then romped by seven lengths in the 2007 Turf on a soft turf course at Monmouth Park. He’s since become another good North American sire.

European shippers won the next four runnings of the Breeders’ Cup Turf until 2012, when Little Mike upset Joe Hirsch winner Point of Entry at Santa Anita Park. Little Mike would come back to win the 2013 Joe Hirsch, but the gelding finished seventh in his bid for a Breeders’ Cup repeat.

In 2014, Main Sequence became the sixth horse to win the Joe Hirsch and Breeders’ Cup Turf in the same year. His Joe Hirsch win was actually closer, as the Flaxman Holdings-owned gelding edged Twilight Eclipse by a neck. One start later, he posted a mild 6.20-1 upset at the Longines Breeders’ Cup at Santa Anita, defeating Prix de l'Arc de Triomphe runner-up Flintshire by 1 ½ lengths. Main Sequence was voted both champion turf male and champion older male for his exploits.

Big Blue Kitten won the 2015 Joe Hirsch and then ran a good third behind elite Euro imports Found and Golden Horn in the Longines Breeders’ Cup at Keeneland discussed above. And in 2016, the aforementioned Flintshire was runner-up in both the Joe Hirsch (to Ectot) and the Longines Turf (to Highland Reel) but was voted champion turf male at the Eclipse Awards anyway. The 2017 Joe Hirsch winner, Chad Brown-trained Beach Patrol, led in the stretch of the Longines Breeders’ Cup Turf at Del Mar before succumbing to European invader Talismanic and losing by a half-length.

Over the past three years, Joe Hirsch runners have continued to make an impact on the Longines Turf. Sadler’s Joy, a pure closer, ran third in the 2018 Joe Hirsch and passed tiring horses late four weeks later at Churchill Downs to finish a distant third behind European mega-stars Enable and Magical. The 2018 Joe Hirsch winner, Bill Mott-trained Channel Maker, would finish second in the 2019 Joe Hirsch to Arklow and then win the race again last year. He subsequently led into midstretch in the Longines Turf at Keeneland but yielded late to European filly Tarnawa and was then edged out of second by Magical. Both Channel Maker and Arklow are listed as probable starters for Saturday’s Joe Hirsch Classic.

Finally, Saturday’s Grade 2 Woodford Stakes Presented by TVG at Keeneland 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. And last year, Leinster and Extravagent Kid finished 1-2 in the Woodford and then checked in 3-4 in the Turf Sprint.

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