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Both get one colt 45.

who wins

Spike puts one between Wolfwood's eyes.

Wolfwood. Nicholas D Wolfwood was at least close to Vash's level.

Yeah, but Wolfwood can't fall out a cathedral with bullet and sword wounds, only to wake up on the couch the next day...

wolfwood was not close to vash' lvl, he was really good with a gun but vash is...well vash, yeah wolfwood is a really good shot but there is nothing to show that he is any better shot than spike, and spike is definately a better hand to hand fighter, only thing wolfwood has against spike is the machine gun built into that cross, but if spike gets close its all over

Wolfwood and Spike go have a drink and become friends.

But to answer your question who would win. Spike is the third biggest bad ass in anime... Wolfwood is the second biggest...