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 41^st World Championships Nov. 1-2 at Del Mar, two of them to the $7 million Longines Breeders’ Cup Classic: the $1 million FanDuel Racing Pacific Classic Stakes Aug. 31 at Del Mar and the $1 million Jockey Club Gold Cup Stakes Sept. 1 at Saratoga.

One more Saratoga race is a “Win and You’re In” event: the Aug. 31 Flower Bowl Stakes for the Maker’s Mark Breeders’ Cup Filly & Mare Turf. Two additional races at Del Mar on Aug. 31 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 Aug. 31 for fillies and the Hopeful Stakes Labor Day, Sept. 2.

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: Saturday, Aug. 31

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 two years ago by the second horse to sweep 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.

2024 field: This year’s Pacific Classic field is missing a standout on the level of Flightline, and therefore should be a good betting race, expected to draw graded stakes winners Dr. Venkman and Reincarnate, among others.

Jockey Club Gold Cup Stakes

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

When: Sunday, Sept. 2

How to watch: FS1

“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 North American Thoroughbred racing. 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 2019 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 Breeders' Cup 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.   

2024 field: This year’s Jockey Club Gold Cup includes last year’s winner Bright Future, but that horse and several other good ones are overshadowed by Arthur’s Ride, who emerged as a leading Classic contender with a dominant win in the Whitney Stakes Aug. 3 at the Spa. The Jockey Club Gold Cup will be held at Saratoga for the fourth 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, Aug. 31

How to watch: FS2

“Win and You’re In” for: Maker’s Mark Breeders’ Cup Filly & 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 & Mare Turf debuted in 1999. As with the Jockey Club Gold Cup, the list of also-rans who trained on to win the Filly & 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 & Mare Turf at double-digit odds, and 2012 Flower Bowl runner-up Zagora nearly reached that longshot mark when she won that fall’s F&M 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 & Mare Turf both years. She finished second in the 2014 Filly & 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 F&M 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.

2024 field: This year’s renewal features a quality field led by War Like Goddess. That accomplished racemare won the Flower Bowl in 2021 and finished second in 2022, and those respective years she trained on to finish third in the Filly & Mare Turf at Del Mar and then third against males in the Longines Turf at Keeneland. Other notable entrants are last year’s Flower Bowl winner Parnac (who is partially owned by sports reporters Lindsay Czarniak and Ian Rapoport) and runner-up McKulick. McKulick turned the tables on Parnac at the beginning of August in the Glens Falls Stakes at Saratoga, the local prep for the Flower Bowl.

Del Mar Handicap Presented by Japan Racing Association

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

When: Saturday, Aug. 31

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: Precisionist was a Grade 1 winner entering the 1984 Del Mar Handicap but he was still in many ways a work in progress. The Del Mar Handicap that year was held on dirt and Precisionist entered the race off an unplaced finish in his second career start on grass in the Del Mar Derby two weeks earlier. The Crozier colt dominated in front-running fashion, opening an early six-length advantage and driving to a 1 ¾-length win under Chris McCarron. He was pointed to the inaugural Breeders’ Cup Classic later that fall at Hollywood Park but faded and finished seventh. In his final start of 1984, Precisionist proved much the best in the Grade 1 Malibu Stakes before following with victories in the Grade 1 San Fernando and Charles H. Strub Stakes to start his 4-year-old campaign. But it was the Malibu win that foretold Precisionist’s near future. He defeated Smile by three-quarters of a length to win the 1985 Breeders’ Cup Sprint en route to an Eclipse Award as champion sprinter. Precisionist proved quite versatile and stretched back out to win Grade 1 routes in 1986 in the Californian and Woodward Stakes before running third in that’s year’s Breeders’ Cup Classic. From 1983 through 1988, Precisionist won 20 of 46 starts with six Grade 1 wins and $3,485398 in earnings. He was inducted into the Racing Hall of Fame in 2003.

2024 field: Several West Coast-based turf standouts are listed as probables, led by Gold Phoenix, an Irish-bred gelding that has won the race the last two years for trainer Phil D’Amato. D’Amato has won the Del Mar ‘Cap eight of the last 10 years.

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.

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 in 2022.

The Green Flash and other races:

The Green Flash Handicap was added to the Challenge Series in 2022, 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 the aforementioned Breeders’ Cup Sprint winner Precisionist when it was held on 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.