In its early years, Simpson County, Kentucky was known as a dueling ground. The farm of Sanford Duncan, near the Tennessee state line, was the site of several "affairs of honor." Duncan built an inn where duelists gathered before meeting each other in battle. Among those who dueled in Simpson County was Sam Houston, later the governor of Texas, who in September 1826 severely wounded his opponent, Gen. William White. Dueling in the county ended in 1827.

Jump forward in time to April 22, 1990, when Dueling Grounds racetrack opened for its first race meet: a one-day affair consisting of four steeplechase races, all stakes, worth a total of $1.125 million in purses. The track was initially developed and owned by Bradley Mike Shannon, a Lexington horseman who constructed the track for $12 million on 300 acres adjacent to Interstate 65. Amenities for opening day included the two-story colonial style clubhouse, complete with the "Sly Fox Restaurant", 250 televisions, six concession areas, and 250 reserved bleacher seats at the finish line.

1997 brought about another sale: Turfway Park and Churchill Downs teamed up with three other investors to buy the track for $11 million at auction. Turfway took control of the day to day operations, but the sale did not complete in time for live racing to be conducted during the traditional fall meet. Turfway Park named Roy Erwin as the Dueling Grounds general manager, and Rick Leigh to serve as racing secretary. Leigh already held the same title at Turfway Park. November brought another big change: Dueling Grounds was renamed Kentucky Downs by the new owners in an attempt to rid the track of the images of the past.