On June 19th, Holyfield defends his title for a third time against former heavyweight champion Larry Holmes with a 12th round decision. On November 13, he meets his toughest opponent to date, Riddick Bowe with a grueling 12 round split decision. Holyfield suffers his first professional loss, ending the year at 1-1. Left the boxing arena for the following three years serving 3 years in prison. Stagnating his career record with a staggering 41-1 with 35 KO's.