Deadpool is a super tough assassin. He has healing powers and teleportation. (because of a gadget) His gun skills are unrivaled. No one can take him. Shadowman also has 2 weapons but he’s not even close to his level. Deadpool wins.

Update! I don’t think that Deadpool’s skills will be enough to keep up with Shadowman’s speed anymore. Not to mention that Shadowman also has some pretty deadly attack power. Shadowman wins.