Given the same ability level, same level of equipment, the skier will win virtually every single time. (Insert physics reasoning here). One exception is when two riders of similar ability atempt a run way above their ability level.
Snowboard speed record 125.459mph by Darren Powell (Australia)
Current Skiing Speed record 156 mph by Simone Origone (Italy)
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snowboards, this is because the surface area of the side-ways snowboarder is smaller, so it catches less air molecules.