Orochimaru, Tsunade and Jiraya
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he ended up with 4
I believe during an episode during the filler arc with the three tails/crystal user...
Naruto vs. Haku, Naruto vs. Orochimaru, Naruto vs. Kimimaru, Naruto vs. Sasuke, Naruto vs. Deidara/Sasori, Naruto vs. Orochimaru, Naruto vs. Pain.
Episode 99 is about sealing the three tailed beast and creating a barrier over it
"Naruto: Outbreak" Shippuden #183 (I think it was called Naruto-Itis in english)