Way Superior Kenjutsu , Way Superior Taijutsu , Superior intelligence and battle experience, Juubi Sized Katon, Gunbai Reflection , Izanagi... Madara didnt became the leader of the Uchiha clan for nothing my friend . He cannot be compared to Itachi, despite that latter also beingg a genius in terms of skills and intelligence, Madara is totally on another level and that's all . I don't see Itachi keeping up with Hashirama who was one of the two strongest ninja at that time and before the war's free powerups, He cannot fight for long , and certainly not for days.
I Think Fugaku also wanted Itachi to become the leader of the clan.
L.E.: Also, if it counts for anything, Itachi at fragile age of 13 was the leader of an experienced/elite shinobis of an Anbu Squad which were even older than him. Just another feat
Anyway, Itachi is superior to MS Madara no question about it.
Juubi Sized Katon...how is that even a feat when we are talking about a fight between 2 Mangekyo Users?
In this battle there are jutsus 10x more powerful to be used, not some katon which can be easily avoided. Battle experience, yes. Intelligence? Nah.
See we see this parallel with Hashirama. A calm fighter always wins against a reckless one. Itachi will always be superior in intelligence.
To be frank, Itachi's genjutsu grand superiority will decide a match, like always.
It useless to have better taijutsu when you are stuck in a genjutsu like Tsukuyomi.
Also, you say Madara has izanagi.
Well, Itachi has its opposite, which will work 100% against people like Madara, due to their evil/ignorant nature.
As long as you agree that DSM Kabuto ~ MS Madara(i believe it is >, but whatever), we can agree on the fact that Itachi will win this mid-high diff at most.