No Amaterasu. To death. Sasuke with EMS. Itachi isn't sick. All at their most powerful. Not the edo versions. Takes place in frontier. No Totsuka blade.
Team 2. Naruto is a somewhat more powerful version of B. 9 tails > 8 tails, and Sasuke is the more powerful version of Itachi. EMS > MS. However in the latter pairing it isn't iron clad who would win since Itachi is smarter and uses the MS better than Sasuke despite having a lower level. But Itachi can't beat Naruto even if he overcomes Sasuke. Kurama won't allow genjutsu to work and Naruto trumps Itachi in every remaining category barring intelligence. Even if Susanoo protects Itachi for a time, he has low stamina and it would only be a matter of time before Naruto defeated him.