When did Sasuke surpass Kakashi?

NarutoX28

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Kakashi Was scared against Orochimaru
Only reason Sasuke wasn't was because he waited for when Orochimaru was severely ill and prepared himself by obtaining knowledge on Orochimaru's techniques before-hand. He also deliberately hid some techniques from Orochimaru such as his Raiton manipulation. I don't think Sasuke envisioned himself as being on the level of Orochimaru yet.
 
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