Who had the more challenging fight?

[Sakata Gintoki]

Would the tougher Akatsuki fight go to Kirin Sasuke, who challenged Itachi Uchiha, the member with the TIE FOR highest databook stats in current Naruto? (35.5)
(In the instance I'm making, Itachi goes all out!)

Or Naruto Uzumaki, in the time with his battle with Pain? (Also instance, Deva ready to use powers and Six-Tail unlock can be used.)

Who had the tougher fight in Shippuden?

 

[Ciberr]

Naruto , He had things to protect (Sorta) .

 

[Unorthodox]

tie everybody except for naruto was at 0 chakra


and sasuke have family members to avenge

 

[kakashi owns all]

itachi does not have highest scores, he is tied for highest scores

 

[Blackbelt Nob]

naruto, but really for me sasuke had the best fights since he always got owned and had to be saved

 

[Rayder]

Sasuke had the more challenging fight. His whole life he has been waiting for that fight and has been hating him for that long.
Naruto just met Pain and empathizes with him.

 

[Ultimate Beast]

tie everybody except for naruto was at 0 chakra


and sasuke have family members to avenge

Naruto had jiriaya to avenge