The 1999 Kentucky Wildcats football team represented the University of Kentucky as a member of the Eastern Division of the Southeastern Conference (SEC) during the 1999 NCAA Division I-A football season. Led by third-year head coach Hal Mumme, the Wildcats compiled an overall record of 5–6 with a mark of 2–6 in conference place, placing fourth in the SEC's Eastern Division. Kentucky was invited to the Music City Bowl, where the Wildcats lost to Syracuse. The team played home games at Commonwealth Stadium in Lexington, Kentucky.