The upcoming Labor Day weekend is one of the most highly anticipated three-day stretches on the racing calendar, as Saratoga Race Course’s summer meet concludes, Del Mar in California reaches the second-to-last weekend of its popular summer meet, and the boutique all-turf meet at Kentucky Downs opens.

It’s also a very important weekend for Breeders’ Cup Challenge Series “Win and You’re In” preps. Five races over the holiday weekend offer automatic berths to the 40^th World Championships Nov. 3-4 at Santa Anita Park, two of them to the $6 million Longines Breeders’ Cup Classic: the $1 million FanDuel Racing Pacific Classic Stakes Sept. 2 at Del Mar and the $1 million Jockey Club Gold Cup Stakes on the same day at Saratoga.

One more Saratoga race is a “Win and You’re In” event: the Sept. 2 Flower Bowl Stakes for the Maker’s Mark Breeders’ Cup Filly and Mare Turf. Two additional races at Del Mar are in the Challenge Series as well: the Del Mar Handicap Presented by Japan Racing Association, a “Win and You’re In” for the Longines Breeders’ Cup Turf, and the Green Flash Handicap, added to the series last year as a qualifier for the Breeders’ Cup Turf Sprint.

In addition to these five Challenge Series qualifiers, several other races over the next week have had a significant influence on the Breeders’ Cup, most notably the two final stakes for 2-year-olds racing on dirt at Saratoga: the Spinaway Stakes Sept. 3 for fillies and the Hopeful Stakes Sept. 4.

Here’s come background on the upcoming Breeders’ Cup Challenge Series races as well as other important races over an action-packed Labor Day weekend:

FanDuel Racing Pacific Classic Stakes

Where: Del Mar Thoroughbred Club, Del Mar, Calif.

When: Sept. 2

How to watch: FanDuel TV

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

Accelerate (Eclipse Sportswire)

Why it’s important: The 1 ¼-mile Pacific Classic was first held in 1991 and it quickly became a highlight of Del Mar’s meet and California racing overall. Its list of past winners is impressive starting with inaugural champ Best Pal and then moving on to names such as Candy Ride (2003), Lava Man (2006), Game On Dude (2013), Shared Belief (2014), Beholder (2015), California Chrome (2016), Accelerate (2018), and Flightline (2022). Up until 2018, no horse had won the Pacific Classic and Breeders’ Cup Classic in the same year, although many horses hit the board in both races and one horse – Pleasantly Perfect – won the Breeders’ Cup Classic in 2003 and the Pacific Classic a year later (notably, Hall of Famer Beholder won the 2015 Pacific Classic in dominant fashion, becoming the first and still only female to do so, and added that achievement to three Breeders’ Cup wins, when all was said and done, amassed in her amazing career). In 2018, Accelerate became the first horse to pull off the double for owner Hronis Racing, trainer John Sadler, and jockey Joel Rosario, taking the Pacific Classic by an overpowering 12 ½ lengths and then coming from off the pace to win the Longines Classic at Churchill Downs by a length. 

Best winner during the Breeders’ Cup era: As impressive as Accelerate’s 2018 accomplishments may be, they were surpassed a year ago by the second horse to win both the Pacific Classic and Breeders’ Cup Classic, undefeated Horse of the Year Flightline. The Tapit colt, expertly managed by Sadler for a partnership that included Hronis Racing, had already unleashed one of the best performances in the storied history of the Hill ‘n’ Dale Metropolitan Handicap in June 2022 when he overcame a bad start to win by six lengths. That was nothing compared with what occurred “where the turf meets the surf” Sept. 3. Trying two turns and 1 ¼ miles for the first time in his fifth career start, Flightline briefly pressed a longshot early leader before taking command effortlessly on the Del Mar backstretch under Flavien Prat and then cruising to an incredible 19 ¼-length win, a stakes-record margin, over 2022 Dubai World Cup victor Country Grammer. Sadler trained Flightline up to the Longines Classic at Keeneland, and on Nov. 5 against a strong field the colt reaffirmed his brilliance one final time, romping by 8 ¼ lengths. One of the best dirt racehorses of this century, Flightline was retired to Lane’s End in Kentucky to start a stud career having given modern racing fans their own bona fide superstar to compare with past greats such as Secretariat, Sunday Silence, and Cigar.

2023 field: This year’s Pacific Classic field is missing a standout on the level of Flightline, and therefore will be a good betting race, featuring Grade 1-winning older horses Defunded and Stilleto Boy and accomplished 3-year-olds Geaux Rocket Ride and Arabian Knight, among others.

Jockey Club Gold Cup Stakes

Where: Saratoga Race Course, Saratoga Springs, N.Y.

When: Saturday, Sept. 2

How to watch: FS2

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

Hall of Famer Curlin. (Eclipse Sportswire)

Why it’s important: The Jockey Club Gold Cup dates back to 1919 and is arguably one of the 10 most important races in the history of Thoroughbred racing in this country. It’s been impactful on the Breeders’ Cup Classic since the first World Championships in 1984, and three horses have won both races in the same calendar year: Cigar (1995), Skip Away (1997), and Curlin (2007). In addition, since 1992 five horses that ran either second or third in the Jockey Club Gold Cup have trained on to win the BC Classic later in the fall, starting with A.P. Indy in 1992 and then followed by Blame (2010), Drosselmeyer (2011), Fort Larned (2013), and Vino Rosso (2019). Vino Rosso actually crossed the finish line first in the ’19 Jockey Club Gold Cup but was disqualified and placed second.

Best winner during the Breeders’ Cup era: Curlin and Skip Away both were voted Horse of the Year (twice in Curlin’s case) and are members of the Racing Hall of Fame … but so, of course, is “the unconquerable, invincible, unbeatable Cigar!” as racecaller Tom Durkin described him in the 1995 Breeders’ Cup Classic. That 2 ½-length victory at Belmont Park was the 10^th in a year without defeat for the Bill Mott trainee and 12^th in a row overall, and it followed a one-length triumph in the Jockey Club Gold Cup. Cigar extended his winning streak in 1996 to 16 before finishing a shocking second to longshot Dare and Go in the Pacific Classic, and he also failed in his repeat bid in that year’s Jockey Club Gold Cup and then in the BC Classic at Woodbine, finishing second and third in those races by the same margin – a head. Despite those defeats, Cigar was voted Horse of the Year for a second straight time, and he retired as one of the most popular racehorses of the 1990s.   

Last year’s winner: One of Bill Mott’s best horses of recent vintage, Olympiad, won the 2022 Jockey Club Gold Cup by two lengths under Junior Alvarado, rebounding from a puzzling fourth-place finish in the Whitney Stakes earlier during Saratoga’s meet. Olympiad would close out a career which saw him win eight of 13 starts and earn more than $3 million with a distant runner-up finish behind the above-discussed Flightline in the Longines Classic at Keeneland.

2023 field: This year’s Jockey Club Gold Cup field is led by Grade 1 winner Proxy and multiple graded stakes winner Rattle N Roll. It will be held at Saratoga for the third year in a row after being a staple of Belmont Park’s fall meet for decades.

Flower Bowl Stakes

Where: Saratoga Race Course, Saratoga Springs, N.Y.

When: Saturday, Sept. 2

How to watch: FS2

“Win and You’re In” for: Maker’s Mark Breeders’ Cup Filly and Mare Turf

Stephanie's Kitten wins the BC F&M Turf. (Eclipse Sportswire)

Why it’s important: First held in 1978, the Flower Bowl has been without a doubt one of the most influential Breeders’ Cup prep races in the entire event since the Filly and Mare Turf debuted in 1999. As with the Jockey Club Gold Cup, the list of also-rans who trained on to win the Filly and Mare Turf is comparable with the dual winners in a single year. Three turf females have pulled off the double: Soaring Softly (1999), Lahudood (2007), and Stephanie’s Kitten (2015). Flower Bowl fourth-place finisher Starine in 2002 and fifth-place finisher Shared Account in 2010 both posted upsets in the Filly and Mare Turf at double-digit odds, and 2012 Flower Bowl runner-up Zagora nearly reached that longshot mark when she won that fall’s Filly and Mare Turf at 9.20-1.

Best winner during the Breeders’ Cup era: Stephanie’s Kitten takes top honors here as a back-to-back Flower Bowl winner in 2014 and ’15 who also came 1 ¼ lengths shy of doing the same in the Filly and Mare Turf both years. She finished second in the 2014 Filly and Mare Turf for trainer Chad Brown and owners-breeders Ken and Sarah Ramsey behind Dayatthespa and then underperformed during most of her 2015 campaign, winning only one of four starts heading into a repeat bid in the Flower Bowl. The daughter of the Ramseys’ prize sire Kitten’s Joy regained her best form with a 1 ½-length win in the Flower Bowl and then one start later closed out her career with a 1 ¼-length, off-the-pace score in the Filly and Mare Turf at Keeneland. That marked her second World Championships victory following a win in the 2011 Breeders’ Cup Juvenile Fillies Turf, and Stephanie’s Kitten’s overall résumé of five Grade 1 wins, five other stakes wins, and more than $4.2 million in earnings makes her very much worthy of consideration for the Racing Hall of Fame.

Last year’s winner: Virginia Joy won the Flower Bowl as the second betting choice, defeating 1-5 favorite, 2021 race winner, and third-place 2021 Breeders’ Cup Filly and Mare Turf finisher War Like Goddess by a neck after controlling the pace. Chad Brown-trained Virginia Joy then finished eighth in the Maker’s Mark Filly and Mare Turf at Keeneland, while War Like Goddess, trained by Bill Mott, nabbed third in another World Championships event, the Longines Turf.

2023 field: War Like Goddess was initially listed as a probable starter in this year’s Flower Bowl but was not entered after she missed some training time. McKulick, who defeated War Like Goddess in the Grade 2 Glens Falls Stakes Aug. 3 at Saratoga, headlines a short field.

Del Mar Handicap Presented by Japan Racing Association

Where: Del Mar Thoroughbred Club, Del Mar, Calif.

When: Saturday, Sept. 2

How to watch: FanDuel TV

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

Why it’s important: The 1 3/8-mile Del Mar Handicap dates all the way back to when Bing Crosby and partners opened the picturesque racetrack in 1937, and it was held on dirt until 1969 and again from 1976 through 1985. No horse has won both the Del Mar Handicap and Breeders’ Cup Turf in the same year, but two runners-up in the Del Mar Handicap trained on to take the top prize in the Turf: Great Communicator in 1988 and Kotashaan in 1993. 

Best winner during the Breeders’ Cup era: French-bred Kotashaan entered the 1993 Del Mar Handicap having won four graded stakes in a row earlier in the year, maturing into a top-level turf horse for trainer Richard Mandella, who took over handling of the Darshaan horse after he was transferred from his home country in 1992. As the 2-5 favorite in the Del Mar Handicap, Kotashaan raced off the pace and rallied furiously through the stretch but fell just short at tallying his fifth straight graded stakes, losing to Luazur by a nose. He rebounded in his next start with a four-length drubbing of that rival in the Grade 1 Oak Tree Invitational Stakes and then closed out his North American racing career by unleashing another impressive off-the-pace charge to take the BC Turf by a half-length at Santa Anita Park. Kotashaan made one more start in his career, finishing second in the Japan Cup at Tokyo Racecourse, and was voted Horse of the Year for 1993 as well as champion turf male at the Eclipse Awards.

Last year’s winner: Gold Phoenix rallied six wide to edge favorite Master Piece by a head in the 2022 Del Mar Handicap for trainer Phil D’Amato and jockey Flavien Prat. The Irish-bred gelding then finished two positions behind Master Piece in the Longines Turf, 10th vs. eighth, in a race dominated by Godolphin’s Rebel’s Romance.

2023 field: Gold Phoenix is in good form for a repeat bid in this year’s Del Mar Handicap coming in off of a three-quarter-length score in the Grade 2 Eddie Read Stakes July 30 at Del Mar.

Saratoga’s juvenile stakes:

One of Saratoga’s many historic contests, the Spinaway Stakes was first held in 1881. Now contested at seven furlongs, it is a key prep in unveiling 2-year-old fillies who show the potential to become more than sprinters, and as such it’s been influential on the NetJets Breeders’ Cup Juvenile Fillies over the past four decades. Five sophomore fillies have won both the Spinaway and the Juvenile Fillies in the same year: Meadow Star (1990), Flanders (1994), Countess Diana (1997), Vequist (2020), and Echo Zulu (2021). That’s just the tip of the iceberg in terms of crossover, however, as many other fillies have excelled in both races through the years, including last year’s Spinaway winner Leave No Trace, who finished second to Wonder Wheel in the Juvenile Fillies. Echo Zulu, by the way, has risen to the very top of the female sprinter division in 2023 and just punched her ticket to the PNC Bank Breeders’ Cup Filly and Mare Sprint this fall with an emphatic win in the Ballerina Handicap Aug. 26 at Saratoga.

Saratoga’s Hopeful Stakes dates back to 1904 and has just as much impact on the FanDuel Breeders’ Cup Juvenile Presented by TAA as the Spinaway has had on the Juvenile Fillies. In fact, the connection started in the inaugural Breeders’ Cup year, 1984, when Chief’s Crown won the Hopeful by 3 ¾ lengths and then, four starts later, took the Juvenile at Hollywood Park by three-quarters of a length over Tank’s Prospect. Since then, three more colts have won both races in the same year: Favorite Trick in 1997 as part of an unbeaten campaign that earned him Horse of the Year honors; Shanghai Bobby in 2012; and Forte last year.

The Green Flash and other races:

The Green Flash Handicap was added to the Challenge Series last year, but it’s been a quality prep for the Breeders’ Cup Turf Sprint for most of its 20-year history. It’s been won by some of the best turf sprinters in California, including aptly-named California Flag, who won in both 2009 and 2010. That popular gelding won the second-ever Breeders’ Cup Turf Sprint in ’09 by dictating the pace on Santa Anita Park’s downhill turf course. Another one of Cali’s top grass sprinters, Stormy Liberal, won the 2018 Green Flash by a nose. That came in between back-to-back scores in the BC Turf Sprint, the first at Del Mar and then the second 2 ½ months after his Green Flash win when shipped to Churchill Downs.

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Among other big races over the holiday weekend, the Caesars Sportsbook Del Mar Derby for 3-year-olds on turf has been won by future Breeders’ Cup victors Da Hoss and Val Royal. The Del Mar Mile Handicap for older horses on turf was won by notables such as Breeders’ Cup Classic winner Alphabet Soup and Breeders’ Cup Sprint winner Precisionist when it was held in dirt. Since the race was moved to turf in 2004, its best winner in terms of Breeders’ Cup success has been Obviously, who won the Del Mar Mile in both 2012 and ’13 and then trained on to win the 2016 Breeders’ Cup Turf Sprint. And the Torrey Pines Stakes at Del Mar for 3-year-old fillies on dirt has been won the likes of the aforementioned Beholder (a year after her win in the BC Juvenile Fillies and two months before her first of two wins in the Longines Distaff) and Belvoir Bay (who won the Torrey Pines in 2016 and posted an upset in the Breeders’ Cup Turf Sprint in 2019).

Over at Saratoga, the With Anticipation Stakes for 2-year-olds on turf is represented by a recent Breeders’ Cup winner in Fire At Will, who actually won the With Anticipation in 2021 when the race was rained off the grass and held on dirt. The Mike Maker trainee subsequently won a turf stakes at Belmont prior to shipping to Keeneland and winning the Breeders’ Cup Juvenile Turf at 30.20-1 odds.

Also at Saratoga, the Bernard Baruch Handicap for older horses on turf has been won by Breeders’ Cup Mile victors Steinlen, Lure, and Wise Dan, who took the 2014 Bernard Baruch in his second-to-last career start and after his back-to-back wins in the Mile in 2012 and 2013. And Breeders’ Cup heroines such as Indian Blessing and Safely Kept have won the Prioress Stakes for 3-year-old fillies.

Finally, at Kentucky Downs, the Mint Millions was won by Tourist in 2015 when it was named the More Than Ready Stakes. Tourist trained on to win the BC Mile at Santa Anita Park in 2016 for Bill Mott, and in 2017 Kentucky Downs changed the name of the one-mile grass race to the Tourist Mile Stakes in honor of his accomplishment. It was renamed to reflect a seven-figure purse in 2021.