yes he does and he wins and he becomes a hero
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Episode 208
The first and so far only fight between Naruto and Sasuke was in episodes 52 and 53. There is no information on the next time they will even meet again let alone fight since the manga hasn't been written to the point where they do meet again.
: He does see his dad but he dose not fight him.. : He see's him on episode 349. : What happens is, naruto is fight pain (leader of the akasuki) and he thinks pain killed hinata (BTW, hinata confesses she loves naruto when her and pain have a fight)and as soon as he thinks that, he turns into the 6 tailed fox. After that pain catches him but he gets 8 tails and escapes again, and inside of naruto he is talking to the fox and the fox asks him to unseal the seal, but as soon as naruto gets his 8th tail, naruto's dad comes to his consciousness and he is actshly there!
SPOILER** when she helps naruto fight pain(pein) she says shes willing to protect and fight with him because she loves him
Chapters 430 to like 444. The way the chapters are im guessing that it how much is about Naruto vs. Pain.