Answer
Ken Shamrock fought Royce Gracie in the inaugural UFC "Superfight" on November 12, 1993. The fight was a major upset, as Gracie, a Brazilian jiu-jitsu practitioner, defeated Shamrock, a professional wrestler and kickboxer, by submission. The fight is widely regarded as one of the most important in the history of mixed martial arts, as it helped to legitimize the sport and bring it to a wider audience.