The highly regarded racetrack was set up in the 1990 under the name Dueling Grounds Racecourse. The racecourse’s title came from the historical account of the Sanford Duncan ranch, on whose estate the facility was situated. The farm in question, which was situated in a minor bend of what is otherwise a completely straight Kentucky-Tennessee boundary, was the venue of many duels in the early 1800s, given the fact that dueling was unlawful in Tennessee although it was still accepted in Kentucky.
Sam Houston participated in a fight on this site. These frequent duels however came to an end by 1827. The racetrack carried out only steeplechase events in its twelve months of operation, but did away with the fences and took to flat sporting functions in 1992. The first meeting featured the widely renowned Dueling Grounds International, with a $750,000 purse that remains the biggest in the annals of American steeplechase.
The racetrack experienced a turbulent sequence of monetary hurdles, changes in management ownership, and legal suits, some of which led to the racetrack’s lack of participation in its 1997 race meeting. Again, the racecourse was also used as a performance location and a popular bingo hall. Around mid 1997, the racecourse was bought at a public sale by Turfway Park, Churchill Downs, among other sports investors of the time. Turfway embarked on the everyday administration of the prestigious facility; sometimes having some of its full-time personnel do double work at the newly established racetrack. Shortly after, the name was switched to Kentucky Downs in a new effort to eliminate the stigma that was attached to the Dueling Grounds trademark under its preceding mismanagement. This new arrangement greatly promoted sporting fixtures staged at the Kentucky Downs Racecourse.
Kentucky Downs plays host to an incomplete live racing meeting every year. The 2008 sport meeting featured the Kentucky Cup Turf Festival (which was run seven days after the Kentucky Cup event card at the older name: Turfway) and also prominently featured the Grade 3 Kentucky Cup Turf. Throughout the remaining part of the year, the racetrack operated essentially as an off-track parimutuel wagering venue, offering simulcast betting on most of the country's leading facilities.
Kentucky Downs Racecourse draws numerous patrons principally from the close Nashville, Tennessee marketplace that is located about 64 km to the south, where the other lawful gambling choices are the Tennessee Lottery facilities and riverboat wagering centers that are more than two hours from the racecourse. With improved legislation that permitted casino sporting at racecourses being a subject of numerous political discussion in Kentucky (predominantly in the 2007 governorship campaign), Kentucky Downs benefited as the nearest wagering establishment to metro Nashville, when casinos got a new wave of less stringent licensing.