The 1899 Kentucky gubernatorial election was held on November 7, 1899, to choose the 33rd governor of Kentucky. The incumbent, Republican William O'Connell Bradley, was term-limited and unable to seek re-election.

The governor of the Commonwealth of Kentucky is the head of government in Kentucky. Sixty-two men and one woman have served as governor of Kentucky. The governor's term is four years in length; since 1992, incumbents have been able to seek re-election once before becoming ineligible for four years. Throughout the state's history, four men have served two non-consecutive terms as governor, and four others have served two consecutive terms, the most recent being current governor Andy Beshear, who was re-elected to a second term on November 7, 2023. Kentucky is one of only five U.S. states that hold gubernatorial elections in odd-numbered years.