Japanese TV has hosted a series of strange challenge matches between top female grapplers vs male Judokas. While male vs female rolling sessions are normal in the gym, they are much rarer in a competitive or even exhibition match setting.
Over the years, Japanese TV has featured:
-BJJ female world Champion Mackenzie Dern (then a brown belt) vs a recreational Japanese male Judo Black belt in Bjj rules.
-Before Ronda Rousey became one of the most recognizable and popular mixed martial artists she appeared on a Japanese game show where the standout Olympic judoka took on three men and beat them all.
-Multiple BJJ world champion Kyra Gracie vs male Judoka on Japanese TV.
Here is the first one, Mackenzie Dern vs male Judo player: