Originally posted by: wirm
Because this matchup is hypothetical and not in the series (as far as I know) then the standard rules of "Naruto always wins because of blah blah blah" don't apply.
Here are some points that I'd like to make:
1) Sasuke is MUCH smarter than Naruto. I don't care how tricky Naruto has been in the past, the guy's got the intelligence of a brick.
2) Sasuke is MUCh faster than Naruto.
3) Naruto has no way of blocking the Chidori. He doesn't have sand to protect him, he's not fast enough to dodge, and unlike Itachi, any attempt at grabbing Sasuke's hand would just be amusing.
4) Naruto's victory against Kabuto was luck. There could have been any number of ways that Kabuto could have gotten away, but he didn't. Kabuto's not the kind of guy who hesitates or makes many mistakes.
I believe that he took the rasengan on purpose to guage it's strength. An example of this happening before would be when he took Dosu's attack right before the chuunin exam. Plus, he thought he could heal his way out anyway.