No he can't.
Superman is not only more durable than anyone Hokuto Shinken had been shown to effect but also has a forcefield that would negate the transfer of chi into his system.
Also, Raoh is too slow and would be thrown into space before he can mount an attack.
His best hope is Musuo Tensei and Clark could just dodge him until he tires out.
Which version of Superman?
IC up to modern versions, Raoh isn't strong enough, he isn't fast enough, and as far as I know, Clark's physiology is still Kryptonian, not human. What happened to Ken when he first fought Souther demonstrates what happens to a Hokuto user when he comes up against somebody with a strange body(read: he got wrecked.)
Original and Golden Age Superman, Raoh has a much better chance. But then again this is PC Superdick, so I'd be iffy on exactly what those chances are.
Just everybody please STOP. This terrible thread is dead. Let it rest.
Well, the Superman featured in the OP is from the Public Enemies movie. Ralph might have a shot against that Superman since he seems more around DCAU Supes' league.
Ichigo: What even *are* you?!
Kenpachi: Some say my mother was a train. Some say that I'm a rejected Godzilla monster too strong for the series canon. But everyone says: I'M THE KEEEEENPACHIIIIII!!!!