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Gai was pretty confident in his ability to neutralize the sharingan. We know one method was to focus on the feet and he had an unknown other method which may have consisted of looking at certain angles or something we don't know but I'm sure it would have worked effectively. Would he beat Itachi? I doubt it even with the advantage of not getting hypnotized Itachi is a fierce opponent and there are other ways to use sharingan to your advantage, such as anticipating attacks as well as hand seal motions which is likely how Kakashi was able to do Zabazu's hand seals at the exact same time. He could anticipate the next seal the same way Sasuke could see Naruto's next move. But we don't know what else Gai is capable of besides everything he taught Lee and summoning frogs. Gai would probably give Itachi a good fight. Kakashi might even be a better opponent if they had a rematch. But I doubt either would win.
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