Originally Posted by kidistight
Technically he didn't hold his own against him since they never fought just a staring competition. Still the only reason Gai "held his own" is because he has fought Kakashi so many times that he had to learn to fight against the sharingan some way. On the other hand Kakashi hasn't fought anyone else with a sharingan until then so he didn't know how to approach the fight. He didn't necessarily freeze up he just realized he was in a lose lose situation with Oro, he did come up with the plan of using chidori against Oro. Besides what defines someone locking up Oro didn't take Sasuke right then and there, we can argue many reasons why. Perhaps he didn't want to fight with Kakashi because it would bring more ninjas for a fight he wasn't ready to have at that time, or the VERY long shot he was scared of Kakashi. Regarding his fight with Itachi he did get caught with his pants down in there fight because of the sharingan but you won't always make the right decision in a brand new situation. I don't think Kakashi had ever seen or heard of that sharingan before that time, but after that he went back to the drawing board to try and prepare for the next fight.
I am just saying, in general. I knew you were going to reply with the, "Gai has fought Kakashi's sharingan so many times," thing. I agree. But Kakashi as a jounin, SHOULD HAVE been better prepared than that. He knew he was facing a powerful sharingan user, and he could've compiled a better plan.