The duo wins. Kakashi isn`t that much faster than Asuma at all, and he doesn`t walk around with a long range weapon like Hidan did to keep Asuma at the defensive so well. It will come to a close range element clash.
He will have to pretty much fight a tactical guy like Shikamaru who is trying to distract him and face someone who got some better stats than his (and vice versa) but with an advantage in the nature of weapons. Hidan pulled it off because he had the curse half done and was immortal which enabled him to ignore the tactical course Asuma used on him.
Kakashi is not that lucky.
He will have to pretty much fight a tactical guy like Shikamaru who is trying to distract him and face someone who got some better stats than his (and vice versa) but with an advantage in the nature of weapons. Hidan pulled it off because he had the curse half done and was immortal which enabled him to ignore the tactical course Asuma used on him.
Kakashi is not that lucky.