As the road to the 2024 Breeders’ Cup World Championships picks up momentum in mid-September, the focus for the upcoming weekend shifts to Woodbine in Toronto, which will host three Challenge Series “Win and You’re In” races on Saturday, Sept. 14.

The marquee event is the $1 million Rogers Woodbine Mile Stakes, a prestigious turf event that offers the winner an automatic berth in the FanDuel Breeders’ Cup Mile Presented by PDJF. Two other races on the card, the $500,000 bet365 Summer Stakes and the $500,000 Johnnie Walker Natalma Stakes, offer “Win and You’re In” berths to the Prevagen Breeders’ Cup Juvenile Turf and the Breeders’ Cup Juvenile Fillies Turf, respectively. The 41^st annual Breeders’ Cup will be held this year at Del Mar: the two juvenile turf races referenced above will be held on Nov. 1, and the FanDuel Mile will be held on Nov. 2.

Three other races held over the weekend on these shores have been influential in sending horses to the Breeders’ Cup over the years, particularly the Iroquois Stakes and Pocahontas Stakes, two dirt stakes for juveniles held at Churchill Downs on Saturday. Both of those races were removed from the Challenge Series in 2022.

In addition to the three “Win and You’re In” races at Woodbine on Saturday, there will be a total of five Challenge Series events held in Ireland over the weekend, at Leopardstown Racecourse Saturday (three) and at The Curragh Sunday (two). They are: the KPMG Champions Juvenile Stakes (Prevagen Juvenile Turf); the Royal Bahrain Irish Champion Stakes (Longines Breeders’ Cup Turf); and the Coolmore America Justify Matron Stakes (Maker’s Mark Breeders’ Cup Filly & Mare Turf), all on Saturday; and Sunday’s Al Basti Equiworld Dubai Flying Five Stakes (Breeders’ Cup Turf Sprint) and Moyglare Stud Stakes (Juvenile Filllies Turf).

Here’s some background on the three “Win and You’re In” qualifiers at Woodbine and other races of note scheduled for the upcoming weekend:

Rogers Woodbine Mile Stakes

Where: Woodbine, Toronto, Ont.

When: Sept. 14

How to watch: FanDuel TV

“Win and You’re In” for: FanDuel Breeders’ Cup Mile Presented by PDJF

World Approval (right) wins at Woodbine in 2017. (Eclipse Sportswire)

Why it’s important: This race, which is second only to the King’s Plate in terms of prestige during Woodbine’s meet, has had a rich history since its first running in 1997 – prior to that it was called the Molson Export Million Stakes and held on dirt at 1 1/8 miles. Its crossover with the World Championships began in ’97 when Woodbine Mile winner Geri shipped to Hollywood Park and finished second in the Breeders’ Cup Mile. Since then, four horses have won the Woodbine Mile and its Breeders’ Cup companion in the same calendar year: Wise Dan in 2012 and 2013, World Approval in 2017, Modern Games in 2022, and Master of The Seas last year. But Court Vision and Hall of Famer Tepin won both races in different years and, on top of that, a handful of also-rans in the Woodbine Mile improved enough to win the Breeders’ Cup Mile during the same year. In Tepin’s case, the elite racemare romped in the BC Mile in 2015 at Keeneland and in 2016 overcame a bad start to win the Woodbine Mile, which would be her final career victory in a career that netted more than $4.4 million in earnings.

Best winner during the Breeders’ Cup era: World Approval was voted champion turf male in 2017 after impressively winning the Woodbine Mile and Breeders’ Cup Mile back-to-back, and so were both Modern Games and Master of The Seas after their recent two-fers … but Wise Dan received that honor as well in both 2012 and 2013, and he was voted Horse of the Year in both years, too. The popular gelding’s first Woodbine Mile win came by 3 ¼ lengths and was the second in what turned out to be nine consecutive victories spanning 2012 and ’13. It was followed in 2012 by a win in the Shadwell Turf Mile at Keeneland and then a 1 ½-length score over Animal Kingdom in the Breeders’ Cup Mile at Santa Anita Park.

The last of Wise Dan’s nine consecutive wins came in the 2013 Woodbine Mile, where he romped by 3 ½ lengths, and then the streak came to an end when he finished second in the Shadwell Turf Mile after it was moved off the turf and onto what was at the time Keeneland’s all-weather track due to rain. Wise Dan rebounded to post his second consecutive win in the Breeders’ Cup Mile in his next start, this time by three-quarters of a length at Santa Anita, and then won four more graded stakes in 2014 before having to miss a planned three-peat attempt in the Breeders’ Cup due to an ankle injury. He trained in 2015 but was officially retired that fall by owner Mort Fink without making another start and concluded his sensational career with a record of 23 wins and two seconds in 31 starts and more than $7.5 million in earnings. In his final 22 starts, Wise Dan won 19 times and finished second twice, and on turf during that stretch he went 15-for-16.

Last year’s results and this year’s field: Godolphin, trainer Charlie Appleby, and jockey William Buick continued their excellence in this race following Modern Games’ win in 2022 as another superb runner, Master of The Seas, romped by 3 ¾ lengths in his North American debut. That gelding would subsequently come up just short when second to Up to the Mark in the Coolmore Turf Mile Stakes at Keeneland in October but then rebound to post a thrilling nose win over his stablemate, the filly Mawj, in the FanDuel Mile Presented by PDJF at Santa Anita Park. Master of The Seas is not listed as a probable starter for this year’s Woodbine Mile by track officials, but these connections still have a shot at the three-peat with Naval Power, who has finished runner-up in two Grade 1 turf stakes since shipping to this continent.

bet365 Summer Stakes

Where: Woodbine, Toronto, Ont.

When: Sept. 14

How to watch: FanDuel TV

“Win and You’re In” for: Prevagen Breeders’ Cup Juvenile Turf

Why it’s important: This one-mile race made its first impact on the World Championships a year before the Breeders’ Cup Juvenile Turf was first held in 2007, when a top-class daughter of Rahy won the Summer Stakes and then a Breeders’ Cup race on dirt (see below). Since 2007, one runner has captured the Summer-BC Juvenile Turf double, and that came in 2010 when Pluck won both races by one length for owner Team Valor International and trainer Todd Pletcher.

Best winner during the Breeders’ Cup era: In fall 2006, the Wayne Catalano-trained filly Dreaming of Anna won the Summer Stakes on turf, defeating males, and then shipped to Churchill Downs and won the Breeders’ Cup Juvenile Fillies on dirt by 1 ½ lengths, with jockey Rene Douglas aboard in both races. Dreaming of Anna received the Eclipse Award as 2006 champion juvenile filly and continued to race at a high level through 2008, winning six more stakes on grass. She was retired with a record of 10 wins, three seconds, and one third in 17 starts with more than $2 million in earnings.

Last year’s results: Fan favorite Carson’s Run, named after Carson Jost, a young man who has a rare condition called Wolf-Hirschhorn syndrome, defeated post-time favorite My Boy Prince by 2 ¼ lengths in the Summer Stakes. Both returned for the Prevagen Juvenile Turf, with Carson’s Run finishing ninth and My Boy Prince a good third behind a pair of European runners. Both colts have trained on to win important stakes races this year as 3-year-olds.

Johnnie Walker Natalma Stakes

Where: Woodbine, Toronto, Ont.

When: Sept. 14

How to watch: FanDuel TV

“Win and You’re In” for: Breeders’ Cup Juvenile Fillies Turf

Catch a Glimpse in 2015. (Eclipse Sportswire)

Why it’s important: The one-mile Natalma has had a significant impact on the Breeders’ Cup Juvenile Fillies Turf since the latter race was first held in 2008; however, only one filly has won both races in the same calendar year (see below). But three also-rans in the Natalma – More Than Real in 2010, Stephanie’s Kitten in 2011, and Pizza Bianca in 2021 – would train on to win the Juvenile Fillies Turf weeks later.

Best winner during the Breeders’ Cup era: Catch a Glimpse, trained by Woodbine maestro Mark Casse, came into the 2015 Natalma Stakes having won her second career start, and first on turf, by 1 ¾ lengths at the Toronto track in August. She improved considerably in the Natalma, leading at every point of call and winning by five lengths under up-and-coming jockey Florent Geroux. One start later in the Juvenile Fillies Turf at Keeneland, the filly sat just off the early pace, took command in early stretch, and outfinished European shipper and favorite Alice Springs to score by three-quarters of a length. Catch a Glimpse received three Sovereign Awards as Canada’s Horse of the Year, champion grass mare, and champion 2-year-old filly of 2015. The City Zip filly maintained top form into the summer of 2016, winning her first five starts of her 3-year-old season – all in stakes – but finished second by a neck that August in a stakes at Saratoga and was not the same afterward, retiring in spring 2017. 

Last year’s results: Cherie DeVaux-trained She Feels Pretty entered the Natalma off of a maiden win in her first start at Ellis Park and was somewhat overlooked in the parimutuel pools at post-time odds of 8-1. The Karakontie filly turned heads with a dominant 4 ¼-length win under Hall of Famer John Velazquez, and then shipped to Santa Anita and ran a great race in the BC Juvenile Fillies, finishing third by only a half-length, and a head shy of second.

Other weekend stakes:

Click image to purchase shirt.

The Iroquois Stakes and Pocahontas Stakes are the first qualifying points races for the 2025 Kentucky Derby Presented by Woodford Reserve and Longines Kentucky Oaks, respectively. As noted above, they were removed from the Challenge Series two years ago as that schedule was revised to conform to a regional format. They had been qualifying preps for the FanDuel Breeders’ Cup Juvenile Presented by TAA and the NetJets Breeders’ Cup Juvenile Fillies for several years after being moved from Churchill Downs’ fall meet (which occurs after the Breeders’ Cup) and to its September meet in 2013.

No horse has won both the Iroquois and Breeders’ Cup Juvenile in the same calendar year, although Not This Time came oh so close in 2016. The Dale Romans trainee romped in the Iroquois by 8 ¾ lengths and then came up a neck short of eventual champion Classic Empire in the Juvenile at Santa Anita Park. He was retired soon after the Juvenile due to a soft tissue injury and Romans extolled the colt’s talent at the time, saying he was “spooky good.” Not This Time has lived up to that reputation as a young stallion, represented by 2022 champion 3-year-old male Epicenter, 2023 champion turf male Up to the Mark, current sprint sensation Cogburn, and leading long-distance dirt horse Next among a growing list of stellar progeny. 

As for the Pocahontas Stakes, no winner since 2013 has gone on to take the Breeders’ Cup Juvenile Fillies either, but the overall roster is more impressive. Untapable won the first Pocahontas to be held in September back in 2013 and a year later won the Breeders’ Cup Distaff and was voted champion 3-year-old filly. Take Charge Brandi, a disappointing fifth in the 2014 Pocahontas as the favorite, would upset the Juvenile Fillies two starts later at 61.70-1 odds. And Serengeti Empress, the 2018 Pocahontas winner, finished seventh in that fall’s Juvenile Fillies but trained on to be third in the 2019 Longines Distaff and then runner-up in the 2020 Filly and Mare Sprint.

The Fasig-Tipton Locust Grove Stakes at Churchill Downs, originally a turf race, was moved to dirt in 2013. Since then, the best horse to win the race and then shine in the Breeders’ Cup is Blue Prize. That Argentine-bred mare won the 2018 Locust Grove by a nose and then followed by taking a Grade 1 stakes at Keeneland and finishing fourth in the Longines Breeders’ Cup Distaff back at Churchill Downs behind Monomoy Girl. In 2019, Blue Prize won the Distaff at Santa Anita in her final career start and then was offered at the Fasig-Tipton November sale three days later, where she sold for $5 million as a broodmare prospect.

International Races:

Among the five “Win and You’re In” qualifiers run this upcoming weekend in Ireland, by far the most impactful on the World Championships is the Royal Bahrain Irish Champion Stakes at Leopardstown. Three horses have won both the Irish Champion Stakes and the Longines Turf in the same year – Daylami in 1999, High Chaparral in 2003 (capturing a second win in the Turf via a memorable dead heat with Johar), and Auguste Rodin last year – but several more have excelled in a variety of Breeders’ Cup events during their careers, such as the “Iron Horse” Giant’s Causeway (runner-up in the 2000 Breeders’ Cup Classic to Tiznow after winning the Champion Stakes) and Magical (who won the Irish Champion Stakes in both 2019 and 2020 after finishing second to superstar Enable in the 2018 Longines Turf).

As for the other races, Iridessa won both the Coolmore America ‘Justify’ Matron Stakes and the Maker’s Mark Filly & Mare Turf in 2019 (the latter in a 13.20-1 upset), and Glass Slippers scored a double in the Al Basti Equiworld Dubai Flying Five Stakes and the Breeders’ Cup Turf Sprint in 2020.