Road to the Breeders’ Cup: Crucial Preps at Woodbine, Churchill

Wise Dan, shown winning the 2012 Woodbine Mile, also won that race in 2013 along with the Breeders’ Cup Mile in both years. (Eclipse Sportswire)

After a weekend that featured two new domestic “Win and You’re In” qualifying prep races for the Breeders’ Cup World Championships held at Belmont Park and Kentucky Downs, the calendar picks up considerable momentum again in the upcoming weekend, as Woodbine in Toronto and historic Churchill Downs in Louisville will host a total of five Challenge Series races offering automatic berths to the Breeders' Cup on Nov. 1-2 at Santa Anita Park.

Saturday’s slate features the Grade 1 Ricoh Woodbine Mile Stakes, a “Win and You’re In” qualifier for the TVG Breeders’ Cup Mile, and at Churchill Downs, juveniles on the rise will square off in the Grade 3 Iroquois Stakes and Grade 2 Pocahontas Stakes. Those two stakes are qualifiers for the TVG Breeders’ Cup Juvenile and Breeders’ Cup Juvenile Fillies, respectively. The Iroquois and Pocahontas also kick off the 2020 Kentucky Derby Presented by Woodford Reserve and Longines Kentucky Oaks points series.

On Sunday, Woodbine runs the Grade 1 Natalma Stakes and the Grade 2 Summer Stakes. These are Challenge Series “Win and You’re In” races for the Breeders’ Cup Juvenile Fillies Turf and the Breeders’ Cup Juvenile Turf.

In addition to the five North American “Win and You’re In” preps, five more automatic qualifiers are on tap over the weekend in Ireland. Three are set for Saturday – the Coolmore Fastnet Rock Matron Stakes (Maker's Mark Breeders’ Cup Filly and Mare Turf), the QIPCO Irish Champion Stakes (Longines Breeders’ Cup Turf), and Willis Champions Juvenile Stakes (Breeders’ Cup Juvenile Turf). Those races are held at Leopardstown Racecourse.

On Sunday, Ireland’s most prominent racecourse, the Curragh, hosts two more “Win and You’re In” contests – the Derrinstown Stud Flying Five Stakes (Breeders’ Cup Turf Sprint) and the Moyglare Stud Stakes (Breeders’ Cup Juvenile Fillies Turf).

And to top off a very busy weekend, there are also several other stakes scheduled in North America that have had an impact on the World Championships through the years. 

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, and notes on the other stakes that have been significant on the Road to the Breeders’ Cup:

Ricoh Woodbine Mile Stakes

The Ricoh Woodbine Mile has a rich history since its first running in 1997, and the crossover between this signature race north of the border and the Breeders’ Cup Mile began immediately. Inaugural Woodbine Mile winner Geri shipped to Hollywood Park for the Breeders’ Cup Mile and finished second behind European invader Spinning World for owner Allen Paulson and trainer Bill Mott of Cigar fame. In 1998, Woodbine Mile winner Labeeb was third in the Breeders’ Cup Mile and, over the next several years, Woodbine Mile winners continued to make good showings in the Breeders’ Cup Mile on occasion, including Good Journey (third in 2002), Touch of the Blues (second to Six Perfections in 2003), and champion Leroidesanimaux (second to Artie Schiller in 2005). In addition to those horses, 1999 Woodbine Mile fifth-place finisher Silic won the Breeders' Cup Mile two starts later by a neck over Tuzla. The Woodbine Mile was run as the Atto Mile from 1999-2005.

In 2007, fan favorite and Oklahoma-bred Kip Deville was in the midst of a breakthrough season when he finished second by a length in the Woodbine Mile to Shakespeare. But he then unleashed a career-best performance in his next start, powering through the stretch of Monmouth Park’s rain-softened turf course to take the Breeders’ Cup Mile under Cornelio Velasquez. Kip Deville would continue his good form into 2008, and finish second behind Hall of Famer Goldikova in that autumn’s Breeders’ Cup Mile.

Juddmonte Farms' Ventura, trained by Hall of Famer Bobby Frankel, won the Woodbine Mile in 2009, a year after taking the Breeders' Cup Filly and Mare Sprint over Santa Anita's synthetic main track. Durable Court Vision made three consecutive starts in the Breeders’ Cup Mile from 2009-2011, and also appeared in two editions of the Woodbine Mile. The son of Gulch won the Woodbine Mile in 2010 but finished seventh in 2011 to Turallure. He had finished fourth and fifth, respectively, in his prior Breeders’ Cup Mile efforts and was sent off at odds of 64.80-1 at Churchill Downs in 2011, coming out of that seventh-place showing at Woodbine and squaring off against heavy favorite Goldikova, who was aiming for her fourth consecutive Breeders’ Cup Mile win. What commenced was one of the most exciting races in Breeders’ Cup history and a monumental upset win for Court Vision, who edged Turallure by a nearly imperceptible nose, with Goldikova a vanquished third. Court Vision had changed owners and trainers through the years and was by fall 2011 owned by B. Wayne Hughes’ Spendthrift Farm and conditioned by Dale Romans. The Breeders’ Cup Mile was his final career start.

The Woodbine Mile-Breeders’ Cup Mile symbiosis has continued to be strong in the current decade, thanks to champions Wise Dan and Tepin. Wise Dan received Horse of the Year honors in 2012 and 2013, and among the races he won during that timespan were consecutive runnings of the Woodbine Mile and the Breeders’ Cup Mile. In both 2012 and 2013, Charles LoPresti used the Woodbine Mile and the Shadwell Turf Mile at Keeneland as preps for Wise Dan heading into the Breeders’ Cup. The gelding’s only blemish among those six races came in the 2013 Shadwell Turf Mile when it was rained off of the turf and he finished second. All in all, it was an incredible extended streak of excellence by a horse that few will ever forget.

Trade Storm, winner of the 2014 Woodbine Mile, finished third in the Breeders’ Cup Mile as longshots took all top four positions, and Woodbine Mile third-place finisher Bobby's Kitten shortened up in distance and won the Breeders' Cup Turf Sprint with a memorable wide rally through Santa Anita's downhill turf course. A year later, Mondialiste won the Ricoh Woodbine Mile in his first start in North America. He then put forth a valiant effort in his next start, the Breeders’ Cup Mile at Keeneland, that was still 2 ¼ lengths too late to catch dominant winner Tepin. Tepin’s Breeders’ Cup Mile win was the second of what would become nine consecutive victories stretching into fall 2016, ending with a gritty half-length score in the Ricoh Woodbine Mile. She finished second in her final two starts, the last to Tourist in the Breeders’ Cup Mile, before retiring as a two-time champion and a certain Hall of Fame inductee a few years from now.

The 2017 renewal of the Ricoh Woodbine Mile added to the race’s luster as an important Breeders’ Cup prep. World Approval entered the race off of a visually impressive score in the Fourstardave Handicap at Saratoga, and then made it back-to-back Grade 1 wins, taking the Woodbine Mile north of the border by 2 ½ lengths. Shipped to Del Mar for the Breeders’ Cup Mile, the striking gray gelding collected his third top-level win in a row for owner Live Oak Plantation and trainer Mark Casse. Lancaster Bomber, runner-up in the 2016 Breeders' Cup Juvenile Turf, completed the exacta in both the 2017 Ricoh Woodbine Mile and the Breeders' Cup Mile. Based on his stellar late-season run, World Approval was awarded champion turf male honors for 2017.

Iroquois Stakes

Until 2013, both the Iroquois and Pocahontas Stakes were run during Churchill Downs’ November meet and after the Breeders’ Cup, as Turfway Park held the commonwealth’s September dates. In the five years since Churchill has moved both races to its abbreviated September meet, no Iroquois winner has gone on to win the Sentient Jet Juvenile, although Not This Time came oh so close in 2016. The Dale Romans-trained colt, owned by Albaugh Family Stable, romped in the Iroquois by 8 ¾ lengths, and was sent off as the 2.80-1 favorite in the Juvenile. He dueled with fellow Kentucky-based colt Classic Empire through the Santa Anita stretch but came up a neck short. Unfortunately, Not This Time was retired soon afterward with an injury.

Of note: The winner of the 2007 Iroquois was none other than Court Vision, discussed above, who found his true calling on turf later in his career.

Pocahontas Stakes

Untapable won the 2013 Pocahontas Stakes, the first edition run in September, but endured a rough trip and was eased in the 14 Hands Winery Breeders’ Cup Juvenile Fillies. By the end of the next calendar year, the Winchell Thoroughbreds-owned filly was 3-year-old champion female and winner of the Longines Breeders’ Cup Distaff.

The 2014 Pocahontas was won by Cristina’s Journey, with 3-2 favorite Take Charge Brandi tiring late to finish fifth. Take Charge Brandi then performed even worse in the Darley Alcibiades Stakes at Keeneland, finishing eighth – but in her next start, she scored a 61.70-1 front-running upset in the Juvenile Fillies at Santa Anita. That improbable win, followed by two more stakes wins to close out 2014, was good enough to earn her the Eclipse Award as champion 2-year-old filly. 

In 2015, Pocahontas winner Dothraki Queen finished third behind the sensational Songbird in the Juvenile Fillies, and in 2016, Pocahontas winner Daddys Lil Darling checked in fourth behind longshot Juvenile Fillies victress Champagne Room. A year ago, Serengeti Empress dominated the 2018 Pocahontas to emerge as one of the top fillies of her age group; she disappointed in her next race at Churchill when seventh in the Juvenile Fillies but came back this year to win the Longines Kentucky Oaks.

Natalma Stakes

Since the Breeders’ Cup Juvenile Fillies Turf was first held in 2008, the one-mile Natalma Stakes has sent several elite fillies on to the World Championships; however, in the first few years when both races were run, it was the also-rans who had more of an impact. In 2010, More Than Real brought famed chef Bobby Flay to the Breeders’ Cup winner’s circle after scoring a 13.60-1 upset in the Juvenile Fillies Turf at Churchill Downs; the More Than Ready filly had finished second in the Natalma one race before.

The next year, Ken and Sarah Ramsey’s Stephanie’s Kitten finished third in the Natalma, but then won the Grade 1 Darley Alcibiades Stakes at Keeneland on the synthetic main track and followed that with a driving three-quarter-length win in the Juvenile Fillies Turf, again at Churchill Downs. Stephanie’s Kitten would go on to finish second in the 2014 Breeders’ Cup Filly and Mare Turf and then win that same race in her final start a year later. She earned nearly $4.3 million in a probable Hall of Fame career. (Incidentally, 2011 Natalma runner-up Dayatthespa would become an elite turf filly in her own right, just on a slower timetable. She bested Stephanie’s Kitten in the 2014 Filly and Mare Turf and won the Eclipse Award in her division that year.)

More recently, Catch a Glimpse became the first filly to win both the Natalma and the Juvenile Fillies Turf when she did so in 2015. Her three-quarter-length win in the latter race at Keeneland was one of two victories for Mark Casse during the two-day Breeders’ Cup, the other coming with the aforementioned Tepin in the Mile.

Summer Stakes

The one-mile Summer Stakes on Woodbine’s turf made an impact on the Breeders’ Cup the year before the Juvenile Turf was inaugurated, which was in 2007 at Monmouth Park. In 2006, the Wayne Catalano-trained filly Dreaming of Anna raced against males and won the Summer Stakes by an easy 3 ¼ lengths one race prior to scoring a similarly impressive 1 ¼-length win in the Breeders’ Cup Juvenile Fillies on dirt at Churchill Downs. 

Two years after the Juvenile Turf began, 2009 Summer Stakes winner Bridgetown set the pace in the Breeders’ Cup event at Santa Anita and held on strongly to finish a very good second to European shipper Pounced. And one year later, Pluck became the first horse to win both races, scoring by a length in the Summer Stakes and then rallying from last under Garrett Gomez to win the Juvenile Turf by the same margin at Churchill Downs for Team Valor International.

In 2011, Excaper finished second in both the Summer Stakes and Juvenile Turf, and in 2014 and 2015, Summer Stakes winners Conquest Typhoon and Conquest Daddyo – both owned by Conquest Stables and trained by Mark Casse – each finished fourth in subsequent editions of the Juvenile Turf. In 2016, Good Samaritan won the Summer Stakes by 1 ½ lengths, and then ran a good third behind Oscar Performance and Lancaster Bomber in the Juvenile Turf at Santa Anita. He trained on to be a solid turf performer as a 3-year-old and also showed his versatility by switching to dirt and winning the 2017 Grade 2 Jim Dandy Stakes Presented by NYRA Bets. Later in 2017, Graham Motion-trained Untamed Domain captured the Summer Stakes by a neck and then backed that up with a late-rallying second to Mendelssohn in the Breeders’ Cup Juvenile Turf at Del Mar.

Last year, War of Will finished second to Fog of War in the Summer Stakes and would train on to finish a good fifth in the Breeders’ Cup Juvenile Turf. Switched to dirt, he become a classic winner at age 3 when taking the Preakness Stakes.

Foreign races:

The 1 ¼-mile QIPCO Irish Champion Stakes has been won by some of the best European racehorses in the late 20th and early 21st centuries, including the legendary Sadler’s Wells in 1984, the first year of the Breeders’ Cup. In 1998, Irish Champion Stakes winner Swain finished a close third in the Breeders’ Cup Classic behind Awesome Again and Silver Charm on dirt. A year later, Daylami won the Irish Champion Stakes, disappointed when ninth in the Prix de l’Arc de Triomphe in France, but then shipped to Gulfstream Park for Godolphin Racing and scored in the Breeders’ Cup Turf by 2 ½ lengths. And in 2000, the late great “Iron Horse,” Giant’s Causeway, won the Irish Champion Stakes before finishing second in a Group 1 in England and then traveling to Churchill Downs, where he posted a valiant runner-up finish to Tiznow in the Breeders’ Cup Classic.

From the late 1990s  to the present, the Irish Champion Stakes has continued to be an important race on the road to Breeders’ Cup glory, and it became a Challenge Series race in 2009. High Chaparral won the 2002 John Deere Breeders’ Cup Turf at Arlington Park as a 3-year-old and returned in 2003 to win his first two starts in Ireland, including the Champion Stakes over Falbrav. After finishing a good third in the Arc, High Chaparral returned to defend his Breeders’ Cup Turf title at Santa Anita, and the Coolmore-owned colt did just that in a dead-heat thriller with Johar, outfinishing third-place Falbrav by a head. (Islington, a mare trained by Sir Michael Stoute, finished third behind High Chaparral and Falbrav in the '03 Irish Champion Stakes and won Breeders' Cup Filly and Mare Turf a year after finishing third in that race in '02.)

Other Irish Champion Stakes winners of note that participated in the Breeders’ Cup in recent years include Azamour (2004 winner, third in the ’05 Turf) Dylan Thomas (2006 and 2007 winner, fifth in the ’07 Turf); So You Think (2011 winner, sixth in the Breeders’ Cup Classic); The Fugue (2013 winner, third in the ’12 Filly and Mare Turf, second in the ’13 Turf); and Golden Horn (2015 winner before taking the Arc, and then second in the Longines Turf to Found). Decorated Knight earned a berth in the Longines Turf in 2017 when winning the Irish Champion Stakes but was a non-factor at Del Mar when finishing 10th.

The one-mile Coolmore Fastnet Rock Matron Stakes, a “Win and You’re In” qualifier for the Breeders’ Cup Filly and Mare Turf, has had far less World Championships crossover than the Irish Champion Stakes but still more than the three other Challenge Series races held in Ireland over the weekend. Rainbow View won the 2009 edition before shipping to North America for the remainder of her racing career, which included a fifth-place finish in that fall’s Breeders’ Cup Ladies Classic (otherwise known as the Distaff) at Santa Anita. In 2015, Legatissimo was sent off as the 9-10 favorite in the Breeders’ Cup Filly and Mare Turf at Keeneland off of a win in the Matron Stakes; the Coolmore-owned filly and English classic winner stumbled badly at the start but rallied late to finish second behind Stephanie’s Kitten.

Another top-class Coolmore filly, Alice Springs, ran second in the 2015 Breeders’ Cup Juvenile Fillies Turf to Catch a Glimpse, and a year later won the 2016 Matron Stakes. The daughter of Galileo ran in the ’16 Breeders’ Cup Mile rather than in the Filly and Mare Turf, and finished 10th in the Mile.

Last year’s Matron fifth-place finisher, Coolmore’s Magical, shipped to Churchill Downs after making two more starts with one win and gave the great Enable all she could handle in the Longines Breeders’ Cup Turf, finishing a game second by three quarters of a length.

Other weekend races:

The Locust Grove Stakes at Churchill Downs was held on turf until 2012. Since 2013, it’s been carded at 1 1/16 miles on dirt, with 2014 winner Don’t Tell Sophia going on to finish second behind Untapable in the Longines Breeders’ Cup Distaff. Last year, Blue Prize held on to win the Locust Grove by a nose during a stellar fall campaign that saw her win the Grade 1 Juddmonte Spinster Stakes at Keeneland in her next start and then finish fourth in the Distaff back at Churchill. 

Woodbine also holds three graded stakes on Saturday bolstering its Ricoh Woodbine Mile card – the 1 1/8-mile Canadian Stakes for fillies and mares, the Northern Dancer Turf Stakes at 1 ½ miles, and the Bold Venture Stakes at 6 ½ furlongs. The best turf female to hit the board in the Canadian Stakes and then make a mark on the Breeders’ Cup was undoubtedly 2008 champion Forever Together. The Augustin Stable-owned gray finished third and second in the ’08 and 2009 runnings of the Canadian, and in three consecutive editions of the Filly and Mare Turf she finished first in ’08, third in ’09, and sixth in a dead heat in 2010, her final start.

The Northern Dancer Turf was first held in 1994, and, as Woodbine’s traditional prep for the Pattison Canadian International Stakes in October, rarely sends its top finishers onto the Longines Breeders’ Cup Turf held two to three weeks later. In 1998 Chief Bearhart, winner of the prior year’s Breeders’ Cup Turf, won the Northern Dancer Turf when it was a listed stakes. The five-time Sovereign Award winner (and Eclipse Award winner in 1997) would finish fourth in the ’98 Breeders’ Cup Turf, his second-to-last career start. Better Talk Now, the beloved gelding and winner of the 2004 Breeders’ Cup Turf, finished third in the ’03 Northern Dancer Turf just as he was getting his lengthy career into high gear. As for the Bold Venture Stakes, held on Woodbine’s synthetic main track, the best Breeders’ Cup horse to win that race was Fatal Bullet, who took back-to-back runnings at Woodbine in 2008 and 2009 and finished second to Midnight Lute in the ’08 Breeders’ Cup Sprint. Mongolian Saturday did finish 10th in the 2014 Bold Venture and won the Breeders’ Cup Turf Sprint a year later in an upset.

Outside of the Woodbine Mile, Monday’s Grade 2 Presque Isle Masters Stakes over Presque Isle Downs' synthetic Tapeta Footings surface has had more crossover with the Breeders’ Cup than any other race held in the next week. Since it was first held in 2007, three winners of the 6 ½-furlong sprint have won the Breeders’ Cup Filly and Mare Sprint. Informed Decision won the Presque Isle Masters in 2009 and 2010, and the Filly and Mare Sprint in 2009. Musical Romance won both races in 2011. And the great Groupie Doll won both races each in 2012 and 2013. All three racemares received Eclipse Awards in the years they doubled up.

The 2017 edition of the Presque Isle Masters certainly lived up to the race’s history of Breeders’ Cup influence. Ami’s Mesa defeated Bar of Gold by a length in a driving finish, and seven weeks later the two racemares squared off again in an ultra-competitive Breeders’ Cup Filly and Mare Sprint. Ami’s Mesa took command in early stretch and appeared on her way to pulling off an 18.10-1 upset … only to be nosed out by a fast-flying Bar of Gold at the wire in one of the most exciting races on a memorable Breeders’ Cup Saturday card. Bar of Gold had added a sixth-place finish in the Grade 1 Juddmonte Spinster Stakes at Keeneland between her appearances at Presque Isle and Del Mar, accounting for her gargantuan 66.70-1 post-time odds in the Filly and Mare Sprint.

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