No, they never fought.
ot: It's pretty simple, actually.
He basically had this:
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He had chest pain and cardiovascular problems & got sick due to being too stressed out/upset. He worried very much. His health failed him because he wouldn't take care of himself by taking time to relax and move away from his aims.
Note: The novels never explicitly state the disease, but they do make clear he got cardiovascular sickness due to stress. Don't know if SP will take time to make that clear in the anime as this is a pretty clear reason given his life, but you never know.
Well i stop watch anime long ago and just wait until it finish to start a real good marathon on it and i dont read novel.
I only read the manga and that is where the original idea come from. Maybe after all of this time Kishimoto decide to change the outcome of some event in the manga, but that is too late. The story is already published and has ended.
Here is the evident that he gave us in the past :
Itachi looks healthy and always calm and quite. Even when he cast ms tech against Kakashi or other character he is still being ok.
In 30% clones, Itachi failed his tsukyomi but still being calm. In full version, Itachi failed another tsukyomi he got shocked in his eye.
Well you can say different body, different after effect or i can say Itachi has spend most of his stamina in his previous fight with Obito, that is why his body/eye got worn-out. Both of this statement can be true.
Obito say out loud when everybody found out that Sasuke won and Itachi is dead : "I didnt see it coming". But in his thought (black screen = dark mind, even if he say it out loud doesnt change anything) : "Nope, just as i predicted".
I see you are an "expert" mangareader, what do you think about that statement ?
For me, i think the author want to show us that Obito doesnt trust Itachi and planned out to get rid of Itachi.
Chapter when Obito meet Sasuke for the first time, the author keeps imply that the partnership between Itachi and Obito has broken. If Itachi could spare Orochimaru, despite Orochimaru being great threat to Konoha then why he want to kill Obito now. Ofc Itachi main goal is to keep Konoha safe and Obito main goal is IT, so in the end one would have to perish.
Obito mind "if i didnt keep secret from Itachi, i'd be dead
right now". Why not before but now ?
If you piece all the evident all the pieces together, you will see it doesnt make sense for a such of great story, suddently a character collapsed on the ground because of unknown disease/heart attack. It is also doesnt make sense to explain it when the story has ended long ago. The only explaination that is legit is what i have mentioned from above. Plan changed and both trying to get rid of each other, Itachi managed to survive (so does Obito) and planned out a new plan for his brother since he is going to die or on the verge of dying because of the incident that "Obito has predicted".
Ofc he could have predicted the disease, but it doesnt make sense as it was not mentioned before and why he is so confident into that matter. Maybe Kishimoto want to change the event to match the filler/novel source.