Itachi vs Asuma (Taijutsu battle)

[Masked man]

Itachi can use Sharingan to see Asuma's movies.

Asuma starts with his chakra blades.

 

[Lilt]

So it's not truly a taijutsu battle, but one involving weapons. They are about equal in hand to hand skill, but Itachi is faster and has precognition. If Killer Bee didn't cut Itachi quickly, then Asuma probably won't do so. And similar to his battle with Killer Bee, if Itachi adopts the strategy to fall back and unleash shuriken jutsu with his hand speed, then Asuma probably won't have the reflexes and hand speed to react in time, as Sasuke needed both the Sharingan and the lightning-draw technique, whereas Bee used partial transformations to tank the attack (the same jutsu he used to counter Hiraishin.)

 

[Icelerate]

Itachi most certainly wins a taijutsu exchange. He is leaps and bounds faster than Asuma as well as better skilled in hand to hand combat. Itachi also has the sharingan so landing a hit against him for someone of Asuma's level will be tough. I don't want to underrate Asuma because I do believe he is underrated but Itachi is probably one of the most skilled ninjas in the manga and doesn't need OP abilities to dominate against jounin level ninjas.

Asuma's chakra blades do give him an advantage so I guess it will be close if Itachi is not allowed to use bunshin feints. Still I go with Itachi high difficulty.