Even though I like He-Man more than Conan, the same reason that makes me prefer He-Man over Conan would mean the Cymmerian's triumph: Conan is much more brutal. Of course, in a battlefield, He-Man could find a clever way to win, or the battle would be interrupted by the arrival of the villains, but in a tournament battle Conan would sweep the floor with the hero of Eternia. Sad, but true.
Just like



PS: You're right, Sundance. That Predator would make Boba share his dad's fate, but I guess the Mandalorian could defeat the renegade Predator from Batman vs Predator II.