Re: VS Thread [With Manga Spoilers!]
Itachi vs Gaara would be one sided on Itachi's case. Not because he's fast and has a bunch of jutsu. Simply because Itachi could make Gaara relive all the pain he's gone through since childhood, which would probably drive Gaara insane and thus making it easy for Itachi to win.
Lee 6 gates vs Steriod Chouji = Lee wins. Lee has both strength and speed during this time, unlike Chouji who even though gains a little speed is no where near enough to fight against the gates strength and agility.