Obito is currently destroying Kakashi, and Naruto looked like Madara was too much for him. Unless Naruto goes into the other dimension and Kakashi fights Obito and Naruto stabs him in the other world. . .yea Obito still wins ha.
Well if kakashi dies, and Obito doesn't get TNJ'd i see no way in hell naruto and co are gonna be able to cope with him let alone hit him, so i think Kakashi will take this
Obito - he has Mokuton, don't forget about it. But like in most of battles the strongest can alwaays lose. In the end nobody cares whether you were stronger or smarter - if you win - so you are stronger per se.