He is first seen in chapter 35/episode 20.
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Naruto episode 216
Naruto meets Sai right after returning from his mission to save Gaara. In the manga that would be book 32.
Shippuden 31 or 32. ^^
They havent fought yet. In the manga (book) sakura is going to find him, to try to kill him. She knows now, that its too late for Sasuke. He is a wanted rouge ninja. So, she figures, if anyone is gonna kill him, it has to be her. we don't know who will win, because they fight hasn't started yet. ill read it when it comes out and let you all know
Episode 117