Kimimaro vs Itachi
Before you say Itachi, I have restrictions to put up. No MS, that means no Amaterasu, Tsukuyomi or Susano'o. Itachi only has three tomoe Sharingan.
Also, read Kimimaro's page. http://naruto.wikia.com/wiki/Kimimaro
Location is where Itachi and Kisame fought Kakashi, Asuma, Kurenai and Gai.
Both are healthy, even if they're sick, it won't matter since they probably have the same sickness.
I personally think that Kimimaro would take this. Kimimaro scored a 5 for Taijutsu and Itachi only has a 4.5, Itachi's faster than Kimimaro but Kimimaro's still really fast. I know Itachi's Sharingan could help him read Kimimaro's movements but I still root for Kimimaro.