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I'm not sure if you caught on yet, but most of these amazing feats against sharingan users is usually when they rarely if not at all used genjutsu in battle. and when they finally decide to use their weak genjutsu, it drastically changes the fight into their favor. itachi is not one of those users, his gen is more consistently used and is strong. in his bout against kakashi and naruto, the fight ends relatively fast and that was just itachi with 3T (no killing intent). susanoo w/ genjutsu should be enough to take them out in time. I'm not saying itachi could take them all out at once, i'm simply saying in the same circumstances sasuke was in, itachi should be able to successfully put it off. he made a joke out of 3 elite jounins with just genjutsu and shadow clone, I can't even imagine what a serious killing intent itachi is capable of.
All at once naw Itachi not winning. Same circumstance as Sasuke? Of course if his stamina allows it. Thats what Sasuke had against him also.