The first full weekend in October is traditionally one of the busiest and most important in North American Thoroughbred racing, as the final round of “Win and You’re In” qualifying races for the Breeders’ Cup World Championships are held at various racetracks.

Several of them anchor what’s become a destination event in the sport each autumn: Keeneland’s Fall Stars Weekend. The three-day span, which kicks off on the Lexington, Ky., track’s opening Friday and ends Sunday, features a bevy of graded stakes races that are held in front of upwards of 20,000 spectators on average each day.

This year, eight Keeneland stakes are Challenge Series “Win and You’re In” races. The winner of each race receives an automatic berth to a corresponding Breeders’ Cup event, with entry fees waived and travel expenses provided. The 40^th annual Breeders’ Cup are set for Nov. 3-4 at Santa Anita Park in California.

Two other stakes races at Keeneland discussed below are not official Challenge Series qualifiers but still have been influential in Breeders’ Cup history. Enjoy this preview of Fall Stars Weekend, where you just might see one, two, or more horses visit the winner’s circle at the picturesque central Kentucky track and then achieve even greater glory four weeks later at the Breeders’ Cup.

Coolmore Turf Mile Stakes

When: Saturday, Oct. 7

How to watch: CNBC and Peacock/FanDuel TV

“Win and You’re In” for: FanDuel Breeders’ Cup Mile Presented by Permanently Disabled Jockeys Fund

The great Wise Dan. (Eclipse Sportswire)

Why it’s important: This race, first held in 1986, has been a key prep for the Breeders’ Cup Mile from the outset. Only two horses have won the Turf Mile and BC Mile in the same year, but many other Turf Mile also-rans have made an impression, including Opening Verse and Miesque’s Approval, who finished second and fourth, respectively, in the Turf Mile in 1991 and 2006 before posting upsets in the BC Mile weeks later.

Best winner during the Breeders’ Cup era: Steinlen (1989) and Wise Dan (2012) are the only two Turf Mile winners to take the Breeders’ Cup Mile later in the same year, while Court Vision won both races in different years (Turf Mile in 2009 and the BC Mile in a huge upset in 2011). Wise Dan takes top honors among that trio as he also finished second in the 2013 Turf Mile at Keeneland prior to posting repeat win in the BC Mile. He then won another Turf Mile in 2014. His runner-up finish in 2013 Turf Mile came when the race was moved to the all-weather main track due to rain. Wise Dan missed a three-peat bid in the Breeders’ Cup Mile in 2014 due to an ankle injury, and the Turf Mile at Keeneland turned out to be the final start of a sensational career. He entered the Racing Hall of Fame in 2020.

Last year’s results: Annapolis won the Turf Mile by 1 ½ lengths over Ivar, who was making his third consecutive start in the race after winning it in 2020 and running fourth in 2021. Annapolis ran 11^th in the FanDuel Breeders’ Cup Mile, which was held right back at Keeneland, while Ivar finished a good fourth. Brazilian-bred Ivar also made his third consecutive start in the BC Mile last year, and ran very well each time, finishing third in 2021 and fourth in 2020.

2023 field: Ivar was retired earlier this year, but Annapolis is entered in Saturday’s Shadwell Turf Mile as he bids for a repeat win, where he’ll face recent Ricoh Woodbine Mile winner Master of The Seas and several other formidable contenders.

Juddmonte Spinster Stakes

When: Sunday, Oct. 8

How to watch: CNBC and Peacock/FanDuel TV

“Win and You’re In” for: Longines Breeders’ Cup Distaff

Princess Rooney in 1984. (Tony Leonard photo)

Why it’s important: This race, which dates back to 1956, has commingled with the Breeders’ Cup from year one of the World Championships in 1984, when Princess Rooney followed up a six-length romp in the Spinster with a seven-length blowout in the inaugural Distaff at Hollywood Park. Since then, five more fillies/mares have won both races in the same year – and one of them pulled that feat off back-to-back.

Best winner during the Breeders’ Cup era: The six Spinster-Distaff dual winners are an impressive group, indeed. After Princess Rooney, you’ve got Sacahuista (1986), Bayakoa (1989, 1990), Inside Information (1995), Blue Prize (2019), and Malathaat (2022). Princess Rooney, Bayakoa, and Inside Information are all in the Racing Hall of Fame, and Malathaat has a good chance to receive an invitation in the years to come. Bayakoa’s four wins at the turn of the 20^th century’s final decade give her the edge here. Janis and Frank Whitham’s mare won those races by a combined 22 ¾ lengths. Naturally, Bayakoa was voted champion older female at the Eclipse Awards for both years, and entered the Hall of Fame in 1998.

Last year’s results: Shadwell Stable’s Malathaat coasted to a 5 ¼-length win in the Spinster as the heavy 0.44-1 favorite, and then came back less than four weeks later to contest a star-studded Distaff. In a thrilling finish, the Curlin filly stormed home from near the back of the eight-horse field to edge California shipper and longshot Blue Stripe by a nose, with Malathaat’s familiar rival Clairiere another nose back in third.

2023 field: Malathaat was retired after her Distaff win and Clairiere will not run in Sunday’s Spinster. This year’s Personal Ensign Stakes winner Idiomatic and third-place finisher Nest are scheduled to face off again at Keeneland.

Claiborne Breeders’ Futurity

When: Saturday, Oct. 7

How to watch: CNBC and Peacock/FanDuel TV

“Win and You’re In” for: FanDuel Breeders’ Cup Juvenile Presented by Thoroughbred Aftercare Alliance

Essential Quality (Eclipse Sportswire)

Why it’s important: As with the Spinster, this Keeneland Fall Stars race has had significant crossover with the Breeders’ Cup since the 1980s. Six 2-year-olds have won both events in the same year: Tasso (1985), Boston Harbor (1996), Favorite Trick (1997), Classic Empire (2016), Essential Quality (2020), and Forte (2022).

Best winner during the Breeders’ Cup era: Favorite Trick won all eight of his starts at age 2 for owner Joseph LaCombe, trainer Patrick Byrne, and regular jockey Pat Day. After wrapping up the season with a 5 ½-length rout in the Breeders’ Cup Juvenile, the Phone Trick colt received an Eclipse Award as Horse of the Year along with a champion 2-year-old male trophy. Favorite Trick would go on to have more success at age 3, winning the Jim Dandy and two other graded stakes, but he’ll be remembered for his superlative juvenile campaign, one of the best debuts in recent racing history.

Last year’s results: Forte shipped in from New York off of a win in the Hopeful Stakes and successfully stretched out at Keeneland to win the Breeders’ Futurity by a neck over Loggins. He then backed that up with an impressive score in the FanDuel BC Juvenile, sweeping to the lead in midstretch and defeating odds-on favorite Cave Rock by 1 ½ lengths. Repole Stable and St. Elias Stable’s charge was an easy choice as champion 2-year-old male for 2022.

2023 field: A competitive group of juveniles are lined up for this year’s Breeders’ Futurity, including Hopeful Stakes runner-up Timberlake, dominant Saratoga maiden winner Locked, and Ellis Park maiden winners Awesome Road and Generous Tipper.

Darley Alcibiades Stakes

When: Friday, Oct. 6

How to watch: FanDuel TV

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

British Idiom (Eclipse Sportswire)

Why it’s important: The premier race for 2-year-old fillies at Keeneland has had an impact on the Breeders’ Cup Juvenile Fillies similar to the Breeders’ Futurity for males. Five fillies have won both races in the same calendar year: Eliza (1992), Countess Diana (1997), Silverbulletday (1998), British Idiom (2019), and Wonder Wheel (2022). Another notable filly, Stephanie’s Kitten, won the Alcibiades in 2011 when the race was contested on an all-weather track and then used that as a springboard to victory in the Breeders’ Cup Juvenile Fillies Turf. 

Best winner during the Breeders’ Cup era: Silverbulletday, owned by Mike Pegram and trained by Bob Baffert, won her first three races in 1997 but tired in the Del Mar Debutante to finish fourth. The daughter of Silver Deputy shipped from California to Keeneland and stretched out for the 1 1/16-mile Alcibiades, and that turned on the switch, as she rolled by 2 ½ lengths and launched an eight-race winning streak that included the Juvenile Fillies in her next start, the Kentucky Oaks in 1999, and five other graded stakes. In fact, after the streak ended with a seventh-place finish in the 1999 Belmont Stakes, Silverbulletday won three more graded stakes during her sophomore season. She secured Eclipse Awards in 1998 and 1999 and joined the Hall of Fame in 2009.

Last year’s results: Wonder Wheel, like Forte, shone at Keeneland last fall with two impressive Grade 1 wins. D. J. Stable’s filly led at every point of call and held on to win by a nose over Chop Chop in the Alcibiades, and she was even better in the Juvenile Fillies, as she changed tactics and came from off the pace to prevail by three lengths.

2023 field: Unbeaten Brightwork, winner of both the Spinaway Stakes and Adirondack Stakes at Saratoga, headlines this year’s starters.

Stoll Keenon Ogden Phoenix Stakes

When: Friday, Oct. 6

How to watch: FanDuel TV

“Win and You’re In” for: Qatar Racing Breeders’ Cup Sprint

Champion Runhappy in 2015. (Eclipse Sportswire)

Why it’s important: The Phoenix is the oldest recognized race in North America and dates back to 1831. It was added as a “Win and You’re In” race for the Breeders’ Cup in 2012, and soon after its stature rose as a prep, as both 2014 and 2015 winners Work All Week and Runhappy trained on to capture the BC Sprint.

Best winner during the Breeders’ Cup era: Runhappy certainly deserves mention based on a brilliant 2015 campaign where he won six out of seven starts including the Phoenix and BC Sprint (which was held at Keeneland), but the best Phoenix winner in terms of overall Breeders’ Cup accomplishments is Whitmore. That fan favorite gelding ran in four consecutive editions of the Phoenix Stakes and four Breeders’ Cup Sprints as well from 2017 to 2020. He won the Phoenix in his first try, and then finished second (by a head), second again, and fourth in his final appearance in 2020, when he was 7 years old. The Ron Moquett trainee then targeted the Breeders’ Cup Sprint for a fourth time after finishing eighth, second, and third in his first three starts. With Irad Ortiz Jr. aboard, Whitmore saved ground into the stretch, moved out and found a seam, and charged to score by 3 ¼ lengths at odds of 18.40-1, providing his owners and fans with one of the highlights of an exciting 2020 Breeders’ Cup held at Keeneland during the height of the COVID-19 pandemic. Whitmore retired in 2021 with 15 wins, 13 seconds, and 5 thirds in 43 career starts and more than $4.5 million in earnings.

Last year’s results/this year’s field: Manny Wah, another veteran campaigner, surged late to post a neck win at odds of 17.57-1 in the Phoenix and then ran a decent fourth in the Qatar Racing BC Sprint at 55.09-1. He’s aiming for a repeat victory in Friday’s Phoenix, where he’ll face a solid group including Bango, who recently tied the all-time win record for a horse at Churchill Downs.

Thoroughbred Club of America Stakes

When: Saturday, Oct. 7

How to watch: CNBC and Peacock/FanDuel TV

“Win and You’re In” for: PNC Bank Breeders’ Cup Filly and Mare Sprint

Why it’s important: This seven-furlong race sent winners to take the Breeders’ Cup Filly and Mare Sprint in both 2009 (Informed Decision) and 2010 (Dubai Majesty), and since then, one other filly/mare has pulled off the double …

Best winner during the Breeders’ Cup era: The pride of Frankfort, Ky., Groupie Doll emerged as a champion after trainer Buff Bradley shortened her up in distance during spring 2012. She was at her best that fall, winning the TCA Stakes by 6 ½ lengths on Keeneland’s all-weather surface and then romping in the Filly and Mare Sprint on dirt at Santa Anita Park by 4 ½ lengths. One year later, the daughter of Bowman’s Band was slightly less dominant but still elite, and she followed up a third-place finish in the TCA to Judy the Beauty by turning the tables on that foe in the Filly and Mare Sprint, which was held again at Santa Anita. Groupie Doll was voted champion female sprinter for both 2012 and ’13. Judy the Beauty, meanwhile, won the Breeders’ Cup Filly and Mare Sprint in 2014 and was honored with an Eclipse Award as champion female sprinter for that year.

2023 field: Wicked Halo, who finished third in last year’s Filly and Mare Sprint, is among the starters for Saturday’s TCA along with Yuugiri, who recently defeated her in a listed stakes at Churchill Downs.

Jessamine Stakes Presented by Keeneland November and Castle & Key Bourbon Stakes

When: Friday, Oct. 6 (Jessamine) and Sunday, Oct. 8 (Bourbon)

How to watch: FanDuel TV (Jessamine) and CNBC and Peacock/FanDuel TV (Bourbon)

“Win and You’re In” for: Breeders’ Cup Juvenile Fillies Turf (Jessamine) and Prevagen Breeders’ Cup Juvenile Turf (Bourbon)

Rushing Fall (Eclipse Sportswire)

Why they’re important: These two races for juvenile fillies (Jessamine) and males (Bourbon) are usually loaded with promising Breeders’ Cup prospects that are coming off of maiden or allowance wins. To date, two fillies have managed to win both the Jessamine and Juvenile Fillies Turf and no Bourbon winner has won the Juvenile Turf. There’s an asterisk involved with the latter record, however, as Tiz the Bomb, who took the 2019 Bourbon by three-quarters of a length, then finished second by 1 ½ lengths to European star Modern Games in the Juvenile Turf at Del Mar but paid out as the winner in parimutuel pools. That memorable occurrence, which upsets many horseplayers to this day, came after Modern Games was designated to run for purse money only by stewards due to a gate incident right before the start.

Best winner during the Breeders’ Cup era: The two Jessamine winners who trained on to shine at the Breeders’ Cup are Rushing Fall (2017) and Aunt Pearl (2020). Rushing Fall was simply one of the best turf females of the 2010s, winning 11 of 15 starts for owner e Five Racing Thoroughbreds, trainer Chad Brown, and jockey Javier Castellano for earnings of nearly $2.89 million. Her win in the Jessamine came in her second career start, and the More Than Ready filly followed that up with a three-quarter-length score in the Juvenile Fillies at Del Mar. Over the next 2 ½ years, she won eight more graded stakes, including five Grade 1s, and finished up with a neck loss to European filly Audarya in the 2020 Maker’s Mark Breeders’ Cup Filly and Mare Turf. Rushing Fall won five graded stakes at Keeneland in her career, second only to Wise Dan’s seven in the storied track’s history.

Other races:

The First Lady Stakes Presented by UK HealthCare was removed from the Breeders’ Cup Challenge Series in 2022 after formerly serving as a “Win and You’re In” qualifier for the Maker’s Mark Breeders’ Cup Filly and Mare Turf. The First Lady was first held in 1998 and the BC Filly and Mare Turf a year later, and since then there’s been consistent crossover. Three fillies/mares have won both races in the same year: Intercontinental in 2005 (upsetting the great Ouija Board in the Filly and Mare Turf), Forever Together in 2008, and Dayatthespa in 2014. In addition, two First Lady winners trained on to win the Breeders’ Cup Mile competing against males: Hall of Famer Tepin in 2015 and Uni in 2019. Last year’s First Lady winner In Italian finished second by a length to Euro shipper Tuesday in the Maker’s Mark Filly and Mare Turf and is back again for this year’s renewal.

Also on Saturday, the Woodford Stakes Presented by FanDuel, a 5 ½-furlong turf dash, has sent several entrants on to good showings in the Breeders’ Cup Turf Sprint in recent years, the best being Golden Pal. The Wesley Ward trainee is the only horse to date to win both the Woodford and the BC Turf Sprint in the same year, which occurred in 2021. Golden Pal also won the Woodford last year but could not overcome a bad start in the Breeders’ Cup Turf Sprint back at Keeneland, finishing 10^th as the favorite.