@Jammin @BD_Beno @lakhan220
Here's something I've been thinking about:
When did Naruto and Sasuke surpass Kakashi?
Naruto
Personally, I'd say when Naruto mastered sage mode, he established himself above Kakashi.
I know when Naruto hit Kakuzu with the rasenshuriken, Kakashi did say something about Naruto surpassing him. Though I feel that could also relate to Naruto developing a powerful jutsu that he nor the 4th could do. And remember he didn't master the rasenshuriken and it was a double edged sword, Tsunade banned him from using it cause the damage it caused him. But I guess you could argue they were same tier because of Naruto's chakra reserves, shadow clones, and rasengan variants, not including Kyuubi chakra cause he had no control.
Sasuke
I think right after the timeskip, Sasuke CM 2 could take Kakashi. If you're not counting that since it's Orochimaru, then when he got MS and able to use kagesutchi and create Susanoo with Amaterasu defense.
I think Sasuke 3 tomoe Sharingan(Itachi fight) vs Kakashi is a good one. Sasuke had some things in his favor or at least equaled Kakashi in. Swordsmanship, shurkien jutsu, genjutsu, and he applied chidori in a lot more different ways than Kakashi.