why kiba in the poll?
But yeah shikamaru is way smart, if he trapped lee in his shadow lee wouldnt be able to use his taijustsu to move about and attack him, only way lee could win would be if he could use sheer strength to pull himself out of the shadow strangle or whatever but i dunno if he can.
Shikamaru control him with Shadow Sewing and then stab him, Rock Lee is only strong and Shikmaru has more IQ then, probably like a trap, look at Hidan battle
lee wins. Not only does he have full knowledge on shika's abilities, but in gates he is faster than other guys who can easily evade shika's shadow, and shika's shadow hold can be broken with high levels of chakra, which is what gates afford lee.