As the road to the 2023 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. 16.

The marquee event is the $1 million Ricoh 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 40^th annual Breeders’ Cup will be held this year at Santa Anita Park: the two juvenile turf races referenced above will be held on Nov. 3, and the FanDuel Mile will be held on Nov. 4.

Three other races held over the weekend 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 last year.

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:

Ricoh Woodbine Mile Stakes

Where: Woodbine, Toronto, Ont.

When: Sept. 16

How to watch: NBC, Peacock, 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, three 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, and Modern Games in 2022. 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 was Modern Games after his two-fer last year … 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.

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: Globe-trotting superstar Modern Games, who had won the Breeders’ Cup Juvenile Turf in 2021, shipped from trainer Charlie Appleby’s base in England to Canada for a start in the 2022 Woodbine Mile and romped by 5 ½ lengths over U.S.-based Grade 1 winner Ivar. He then traveled back to England and nabbed second in the Group 1 Queen Elizabeth II Stakes before taking a turnaround trip to North America and rallying strongly to win the FanDuel Mile Presented by PDJF at Keeneland by three-quarters of a length. The Godolphin homebred won one of two starts at age 4 earlier this year before being retired in August.

bet365 Summer Stakes

Where: Woodbine, Toronto, Ont.

When: Sept. 16

How to watch: NBC, Peacock, 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: Mysterious Night, like Modern Games owned and bred by Godolphin and trained by Charlie Appleby, dominated the Summer Stakes by 5 ¾ lengths as the odds-on favorite, but the gelding did not run in the Breeders’ Cup and has finished off the board in all three starts – two in England and one at Saratoga – this year.

Johnnie Walker Natalma Stakes

Where: Woodbine, Toronto, Ont.

When: Sept. 16

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: Last Call pulled off an upset in the Natalma at 21.15-1 odds over favored Cairo Consort, and the top pair started in the Juvenile Fillies Turf as longshots in the 20-1 range going up against tougher competition. Cairo Consort finished a rallying third at Keeneland, while Last Call checked in sixth of 14.

Other weekend stakes:

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The Iroquois Stakes and Pocahontas Stakes are the first qualifying points races for the 2024 Kentucky Derby Presented by Woodford Reserve and Longines Kentucky Oaks, respectively. As noted above, they were removed from the Challenge Series last year 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 last year’s champion 3-year-old male Epicenter along with several other graded stakes winners.

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 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 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.