The Dexter Cup is a harness racing event for three-year-old standardbred trotters raced at a distance of one mile. The race was created in 1960.
The Dexter Cup is a stakes race for three-year-old colts and geldings. Its companion race for three-year-old fillies is called the Lady Suffolk. The Dexter Cup was inaugurated in 1960 at Roosevelt Raceway in Westbury, New York. The inaugural $60,000 Dexter Cup was held on September 17, 1960. Named in memory of Dexter, the race honors one of the foremost trotters of the 19th century.
The Dexter Cup is traditionally considered the initial leg of the "Big Five" trotting stakes, which also include the Colonial Trot, Yonkers Trot, Hambletonian Stakes, and Kentucky Futurity. It is held annually as the opening stakes event of the Grand Circuit season for three-year-old male trotters eligible to compete in the Hambletonian.
The Dexter Cup was held at the now-defunct Roosevelt Raceway from 1960 to 1987. At Roosevelt Raceway, The Dexter developed into the richest harness race of all time with a value of $183,463 in 1967. It was relocated to Yonkers Raceway for the 1988 season. In November 1991, Freehold Raceway signed a contract with the Hambletonian Society to host the Dexter Cup and the Lady Suffolk trots for the first time in 1992. The closure of Freehold Raceway at the end of 2024 led to the Dexter Cup being reassigned to The Meadowlands Grand Circuit program in 2025. The format was changed to eliminate eliminations and a final, instead splitting the race into divisions.
Notable Dexter Cup winners include the world champions Armbro Goal, Joie De Vie, Defiant Yankee, Colt Comfort, Songcan, Lindy's Pride, Nevele Pride, and Carlisle. Five horses have captured both the Dexter Cup and the Hambletonian Stakes: Speedy Scot (1963), Nevele Pride (1968), Lindy's Pride (1969), Armbro Goal (1988), and American Winner (1993).
The Dexter Cup Trot was originally raced over one mile when inaugurated in 1960.