Shikarmaru if he can keep up with the speed and Lee if he is fast enough.

Shikamaru could win with his strageties, but lee could win with his speed. it all just depends.:P

lee would win cause shikamaru gives up if he gets board

it would all depend on the situation the terrian and even the weather yes lee has speed but it wouldn't count for anything if they were fighting some where , where there are ton's of Shadows Shikamaru would have a advantage there if it was in a open plain Lee has a better advantage. yes lee is fast but let's look at his persnailty he's Hot headed arogant and would more than likely rush into thing's and get caught into shikamaru's trap sure he has the whole eight gate's move but again if he's caught by the shadow's that shikamaru prodouce it's over.now let's look at it from lee's point of view lee would most likely be able to get close to shikamaru fast and be able to do some heavy damage as well land a Primary Lotce or two he maybe able to even beat shikamaru let's look at shikamru's persnailty Lazy none-careing and take's almost nothing seriously let's not froget a advantage lee has is his will power witch if he is strong enough could resist the shadow poession jutsu, he also has the eight gates move where that boosts all his pyschail attacks and will power. however let's keep in mind if lee where to use this eigh gate's he'd tired extermely fast and wouldn't have enough energey to dodge or move anymore.but if shikamaru ran out of Chakara he'd do a exit stradgey. so it would be tuff to say who'd win until you actually prodouced a simulated battle

I agree 100% .... Good answer :)

I agree with wolfmaster.

P.S.
I think those two would make a good team.