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The Big Five: Ranking the Best Breeders’ Cup Turf Winners
Legends
While races on the grass play second fiddle behind dirt racing here in America, our nation nonetheless has a rich history on the turf. Many of the greatest horses ever to run in the United States, such as Secretariat, Kelso, and Dr. Fager, took to the turf to prove themselves on any surface. Since its inception, the $5 million, Grade 1 Longines Breeders’ Cup Turf has been America’s most important turf race.
Truly an international affair, the 1 1/2-mile race consistently attracts top runners from around the world in an attempt to win one of the richest grass races in the sport. Dominated in recent years by invaders from Europe, Americans continue to enter their best turf horses in hopes to regain bragging rights for the season. Looking back at the greatest winners of the race is an enjoyable exercise sure to bring back fond memories of both classy international horses, as well as top U.S. turf stars.
Counting down from five, here is my ranking of the best of all the winners from the first 42 editions of the Breeders’ Cup Turf. My ranking is based on which horses I believe to be the overall best during their racing career, with their performance in the race only considered when breaking ties.
5. Rebel’s Romance: One of the great globetrotters of modern racing, the Irish-bred, British-trained star finally retired earlier this year after a sensational seven seasons on the track. A high-class runner on the dirt, he proved even better on the turf, winning important races in the U.S., Dubai, England, Germany, Hong Kong, and Qatar. The trip overseas to the United States for the Godolphin gelding was a common occurrence and he was at his very best in three attempts at the Breeders’ Cup Turf. The winner at both Keeneland in 2022 and Del Mar in 2024, his attempt to become the only three-time winner of the race fell just short when he finished second in 2025. All told, the Charlie Appleby-trained runner won 22-of-32 starts with better than $15.6 million in career purse earnings.

4. High Chaparral: A turf runner of distinction in each of his three seasons of racing, High Chaparral was one of numerous stars from the yard of trainer Aidan O’Brien. A Group 1 winner in England from only three starts as a juvenile, the son of Sadler’s Wells quickly established himself as a star with wins in both the Epsom Derby and Irish Derby in his sophomore season. After finishing third in the Prix de l’Arc de Triomphe in his first try against older horses, he proved too much for the best North American grass horses in the 2002 Breeders’ Cup Turf at Arlington Park. He became the first horse to win the race twice the following season when he returned to the U.S. for the 2003 edition at Santa Anita. That result was actually a dead-heat for the win, as he gamely battled between horses to hit the wire in unison with Johar. A two-time champion in the U.S. while only racing here twice, he retired with an excellent career record of 10 wins, one second, and two thirds from 13 lifetime starts.
3. Manila: The only U.S.-based runner to crack the top five, the impressive son of Lyphard became a star the moment he stepped onto the turf for trainer Leroy Jolley. Manila was an improving runner in his first four starts on dirt, but an allowance romp at Keeneland in his grass debut revealed his true calling. Running in nothing but stakes races after that, he never finished worse than second in 14 career races on the turf. As a 3-year-old, he rattled off six consecutive graded stakes scores, with the last four coming against older competition. In the 1986 edition of the Breeders’ Cup Turf at Santa Anita, he defeated the European superstar Dancing Brave, as well as champions Theatrical and Estrapade. He returned the following year as the dominant turf horse in North America, but after an easy win in the Arlington Million, an injury forced his retirement before he had the chance for a repeat bid in the Breeders’ Cup.

2. Enable: The lone female to make the top five, the English-bred filly became a European Horse of the Year at age 3 with six consecutive stakes victories in England, France, and Ireland. She won the Oaks in both England and Ireland before beating older males in the King George VI & Queen Elizabeth Stakes in her home nation and the Prix de l’Arc de Triomphe in France. Returning from a long layoff, the daughter of Nathaniel came back in time to earn a second victory in the Arc in her second start as a 4-year-old. Four weeks after that, she made her only start in the North America by winning the 2018 edition of the Breeders’ Cup Turf at Churchill Downs. She never returned stateside, but added four additional Group 1 victories to her career total the following two seasons. She retired with a career record of 15 wins, two seconds, and one third from 19 races over five seasons for trainer John Gosden. A member of the British Racing Hall of Fame, she remains the only horse to win both the Arc and the Breeders’ Cup Turf in the same year.
1. Daylami: While perhaps not the most consistent winner of the Breeders’ Cup Turf, at his best this imposing gray was one of the most dominating horses to run on North American turf during the Breeders’ Cup era. The Godolphin runner twice came to the United States and each time closed with an impressive rush to easily sweep to victory in both the 1998 Man O’ War Stakes at Belmont Park and the 1999 Breeders’ Cup Turf at Gulfstream Park. His win in Florida was his final career start in a career that spanned four seasons. A champion in the U.S., he was also the European Horse of the Year in his final season. Besides his perfect record in the United States, the Saeed bin Suroor-trained son of Doyoun won at the highest level in England, France, and Ireland at distances ranging from a mile to 1 ½ miles. His Timeform rating of 138 trails only Dancing Brave as the highest-rated horse ever to compete in the Breeders’ Cup Turf.