On December 31, 2005, Herring was involved in a memorable MMA moment during K-1's Dynamite 2005 show. During the pre-fight staredown, his opponent, Yoshihiro Nakao, leaned in and kissed him on the lips. Herring reacted, delivering a right hook to the jaw of Nakao, knocking him out cold. Herring was immediately disqualified and Nakao was carried from the ring. Shortly thereafter, Nakao's cornermen attacked Herring and a brief fight ensued. Herring's trainers, Ricardo Pires and Sergio Penha fought with Nakao's trainers until security stopped the fight. The fight result has since been changed by K-1 from a disqualification loss for Herring to a no contest, as K-1 judges ruled that Nakao's kiss and Herring's subsequent knockout punch were both fouls.
