Masahiko Kimura vs. Helio Gracie - Kodokan Judo vs Brazilian Judo 1951

In 1955, Kimura, at 38 years old, and 80lbs heavier than Helio, he participated in a match in which he defeated Hélio Gracie of the famous Gracie Jiu Jitsu family in a submission judo match held in Brazil. During the fight, Kimura threw Gracie repeatedly with Ippon Seoinage (one arm shoulder throw), Osoto Gari (major outer reap) *Kimura's signature throw. He threw Helio 3 times with Osoto Gari.*, Ouchi Gari (major inner reap), Uchimata (inner thigh throw), and Harai Goshi (sweeping hip throw). Kimura reportedly threw Gracie repeatedly in an effort to knock him unconscious.

However, Helio proved to be tougher than he looked and Kimura was not able to knock him out. Kimura tried to summit Gracie by using grappling techniques such as kuzure-kamishiho-gatame (modified upper four corner hold), kesa-gatame (scarf hold), and sankaku-jime (triangle choke). Finally, thirteen minutes into the bout, Kimura positioned himself to apply a reverse ude-garami (arm entanglement, a shoulderlock). Gracie refused to submit, but loss the match. Many claim that if Kimura was in the same weight class as Helio, Helio would have won. At the end of the match, Kimura was so impressed by Helios technique that he invited Helio to teach at the Imperial Academy of Japan.

http://en.wikipedia.org/wiki/Masahiko_Kimura