Suggested by Anonymous Isshiki Ōtsutsuki is a powerful fighter who even gave Naruto and Sasuke a run for their money. While Itachi is quite skilled and one of the most powerful fighters in the classic Naruto series, this is a level of power that his genjutsu would not be able to stop. Isshiki can even stop the Amaterasu in its tracks. Itachi may be able to come up with some plans to buy time but ultimately this is a match that Isshiki wins with brute strength. Isshiki Ōtsutsuki wins.
Suggested by Destroyer Itachi has a lot of Sharingan tricks up his sleeve which could pose a threat to Raditz if the villain isn’t careful. He will have to really move with caution if he wants to survive this but the difference in their destructive abilities will be key here. Raditz can always destroy Itachi from afar or just speed blitz him. Raditz wins.
Suggested by Destroyer Magicman is a fairly strong navi who used to be taken seriously until he went all in as a comic relief character. I definitely miss the old days where he was a threat but that definitely didn’t last long. Itachi was always a threat and his sharingan abilities continued to improve as the series went on. It would be pretty easy for him to crush Magicman with a well placed Susanoo slash. Itachi wins.
This is a pretty tricky fight and both of these fighters are some of the strongest Shinobi in the series. Itachi’s sharingan gives him a big boost, but Pain’s Rinnegan is also formidable. Pain’s bodies help to give him the edge since Itachi would eventually be overwhelmed. His array of jutsu is impressive and Itachi is physically a match for Pain as well. Pain’s ninjutsu would just be too much for him to overcome. Pain wins.
Kakashi is a pretty skilled ninja and he definitely deserves some credit for mastering many of the Sharingan’s secrets. That being said, an Uchiha can only be defeated by an Uchiha. This isn’t an absolute, but it’s typically the case thanks to the limitless powers of the Sharingan. Itachi is more proficient at using it and Kakashi would not be able to win in an eye battle. Kakashi’s Lightning Blade would be very dangerous, but Itachi’s Susanoo should be more than enough to protect him. Itachi wins.
Madara and Itachi are both some of the strongest characters in Naruto history. Both of them are very skilled with the Sharingan and they have many lethal attacks. Itachi has shown us more hand to hand skills in the past, but Madara seems to be physically superior to Itachi. It would definitely be a very close fight between these two opponents, but I believe that Madara would be able to take the win. Madara wins.
Red Hulk is definitely a power house! His raw strength is incredible, but now he’s up against an Uchiha! Itachi can activate his sharingan to trap Red Hulk in a genjutsu while he finishes him off. Of course Itachi doesn’t need to use genjutsu to win this round. With his ninjutsu skills Red Hulk will be no match. Itachi wins.