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Sasuke only won against Orochimaru because he had no arms and was in a weak state:
The same Sasuke killed Itachi.
Healthy Orochimaru>3 Tomoe Sharingan Sasuke
3 Tomoe Sharingan Sasuke>Itachi
So
Healthy Orochimaru>Itachi
Orochimaru failed taking Itachis body back then in Akatsuki because he was unprepared but in the end Orochimaru would beat Itachi.
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The same Sasuke killed Itachi.
Healthy Orochimaru>3 Tomoe Sharingan Sasuke
3 Tomoe Sharingan Sasuke>Itachi
So
Healthy Orochimaru>Itachi
Orochimaru failed taking Itachis body back then in Akatsuki because he was unprepared but in the end Orochimaru would beat Itachi.