Board Thread:Versus Debates/@comment-26636534-20180830184727/@comment-4080775-20181002223646

Oro can easily summon Rashomon Gates to divert Itachi's TB, which he already knows about. Konan can easily turn into paper upon being stabbed, not to mention Orochimaru can just use his body replacement technique to escape before he is sealed away. If Orochimaru has access to Kabuto's techniques (Strange Transmission Distant Shadow and the like), he could easily break down his body and escape being stabbed. Not to mention he could use use the genjutsu on Itachi and trap him. Without another Sharingan user to help him escape, he is pretty much screwed.

Orochimaru may have been defeated easily with Genjutsu the first time and the Totsuka Blade the second time, but since he has knowledge of the past encounters, his chances of survival go up exponentially. Even if Itachi catches Oro in genjutsu, Kimimaro and Konan keeping him on the ropes for even a second is long enough for Oro to break the Genjutsu. With access to the KG and abilities of the Sound 4 (5), Orochimaru has a great advantage over Itachi this time around. Add in actual Senjutsu (non curse seal) and his power and range are increased several times over.

Not saying it will be easy, but I don't see Itachi beating Orochimaru this time around.