When i think about it, the only fight he won 1v1 are those from Danzo and Deidara. nvm both are fodders, Deidera was already defeated twice by Sharinggan user, and the other is lame.
Zaku, Yoroi, Base Gaara, Naruto Final Valley Part One, Team 7 at Orochimaru's hideout, Orochimaru, Kid Shin.
Sasuke also had 3 other people with him as compensation though.
3 people that Sasuke had to worry about while fighting Bee. For example, after Sasuke evaded his Hachibi enhanced speed, which Bee stated only the Raikage had done, he immediately attacked his teamates.
Aside fron that, they all had to hold back to capture Bee alive, Sasuke also lost a power that he mastered and incorporated into his fighting style for years - the Curse Mark, and gained a new one in which he had no experience with and couldn't learn how to use and develop through training due to it'a significant negative effects - the Mangekyo.
Despite all this, after the battle, Bee, who retreated because he was low on stamina, stated this Curse Mark-less, weakened, no MS experienced, holding back Sasuke was probably the toughest Shinobi he ever fought.
Orochimaru. Sasuke won only because Oro was on his deathbed.
Sasuke thoroughly studied Orochimaru's abilities/skills in preparation for their battle. Which is why he was able to perfectly replicate them once he absorbed him.
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^He'd been planning on Orochimaru's defeat since the day he went to him. On top of training with Orochimaru, he trained alone as not to let the enemy know his full capabilities. Hence Orochimaru not knowing of his Shape manipulation and thinking the Ritual would work.
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Whether Orochimaru was sick or not he would need to use the Body Tranfer Ritual which Sasuke was fully prepared for and countered easily.
A sick Orochimaru believed it was *impossible* to overcome. Sasuke did so with absolute ease. A healthy Orochimaru would be even more overconfident and face the same demise from underestimating his power and skill.
Sasuke specifically waited for the time when Orochimaru needed to switch bodies so he could reverse the ritual, seal him in the Curse Mark, & acquire his power.
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htttp://mangaseeonline.us/read-online/Naruto-chapter-365-page-8.html
mangaseeonline.us/read-online/Naruto-chapter-122-page-7.html
mangaseeonline.us/read-online/Naruto-chapter-343-page-3.html
Orochimaru confirmed that when he's watching Sasuke, he's wondering why people called him a genius, cause he was nothing compared to Sasuke...think about it.
Based on what the story presented, Orochimaru wouldn't have won regardless of his health.
