Orochimaru vs Itachi



Orochimaru has his snake abilities, but still loses to Itachi in this match. He just doesn’t have the skills to stop him. Itachi will continue to pwn and pwn in the blog. With his sharingan he can take down Orochimaru in an instant. Orochimaru just has no defense against such an attack. Itachi wins.

Jiraiya vs Itachi



If anyone thought that Jiraiya could take on Itachi they’re in for a rude awakening! Back in the old days they kept implying that in a 1 on 1 fight Jiraiya would actually have a chance and maybe beat Itachi. No Way! Sage Mode is a formidable jutsu, but in the end Itachi is still superior. With Susanoo Itachi could easily defeat Jiraiya in an instant. Without it he could burn Jiraiya with Amaratetsu. He could also just beat him with plain sharingan. Jiraiya loses epicly. Itachi wins.

Itachi vs Byakuya




Itachi Uchiha, Sasuke’s “evil” older brother while Byakuya is Rukia’s “evil” “brother”. While Itachi is a formidable foe seeing as how he hasn’t lost yet Byakuya has…BANKAI. With it he’s almost unstoppable. Byakuya is also the 2nd strongest Bleach character ever. Byakuya wins.

DR

Itachi vs Obito




Now this is a battle. They are both First Class ninja who are excellent at genjutsu. They both have also learned much about the sharingan. They are both Uchiha and are arguably the strongest Naruto characters in existence. It’s hard to tell who’s stronger since they’re about even in everything. I pick Itachi because he has the hand to hand edge. Itachi wins.

Update as of 03/01/2017 the verdict has been changed. Obito has completely surpassed Itachi by the end of the series and made the gap in their abilities considerable. Obito is physically on a whole other level and the fact that he also possesses the sharingan assures that Itachi won’t be able to pull any genjutsu tricks over him. Obito wins.