no

Tails thats stupid, Itachi was sticking to the mission at hand which is get naruto not get involved in some fight

Kisame would kill Kakashi, Kakashi's sharingan would in the end drain too much power from him as well as Kisame's shark skin sword for him to do anything powerful, Plus, Kisame has the most regular chakra in the show, Neji even says that Kisame's chakra was equivalent to that of Naruto's when he used the nine tail's power in the chunnin exam, and that was when Kisame was using only 30% of his power because of that jutsu. You also need to take in Kisame's incredible physical strength and speed as well as his monsterous ninjutsus, Kakashi can not win.

Itachi would Own Gai hands down. You all say Gai could win based on the assumption that all Itachi knows is genjutsu, Itachi has the sharingan, so he can stick with Gai in hand to hand until Gai opens up past the 4th gate, and since Itachi is the strongest to come out of the Uchiha clan since Madara Uchiha, you know his ninjutsu is just as good. and the thing is Gai cant control himself in the gates, he won't be able to make his moves as accurate just by looking at Itachi's feet, and when using a technique like the gates he can't afford to make careless efforts by looking at his feet alone, and all Itachi needs is a glimpse of Gai's eyes and then it's game over, he'll make Gai waste his power in the gates using genjutsu. And last thing about this, Itachi doesn't even need his eyes to cast genjutsu, if you recall the genjutsu he put Naruto in with just his finger, that was such an advanced technique and it came from his finger, and don't tell me some bull about how Naruto isnt as experienced as Gai, Naruto trained under Jiraiya who would also beat the living snot out of Gai, and don't even get me started on that