The 1965–66 Western Kentucky Hilltoppers men's basketball team represented Western Kentucky University during the 1965-66 NCAA University Division Basketball season. The Hilltoppers were led by Ohio Valley Conference Coach of the Year John Oldham and OVC Player of the Year Clem Haskins. WKU won the OVC tournament and season championship, as well as the conference's automatic bid to the 1966 NCAA University Division basketball tournament, where they advanced to the Sweet Sixteen and finished 3rd in the Mideast Region. The conference tournament was held in December and had no impact on the conference standing; the conference NCAA tournament bid was awarded to the season champion.