Naruto loses scenario one with high difficulty and wins scenario 2 with medium difficulty especially if he's able to summon the elder toads. Senpo fuuton rasenshuriken, rasengan barrage, frog call, hordes of clones, etc, give him the win. Amaterasu and genjutsu are literally fodder when Naruto can counter them just fine and frs destroys Sasuke and his susanoo before he can use kirin.