The 2008–09 Kentucky Wildcats men's basketball team represented the University of Kentucky in the college basketball season of 2008–2009. The team's head coach was Billy Gillispie, who was in his second and final year as coach. The Wildcats played their home games at Rupp Arena in Lexington, Kentucky. The team's season started with a controversial early Midnight Madness event on October 10, 2008 which is not the traditional date for celebration that coincides with the first day of NCAA-sanctioned regular practice sessions that occurred on October 17, 2008.