Deadpool would win due to the fact that he's a better solider in my opinion. He has fast regenerating health, can teleport, is great with armas and swords, and he can annoy his opponents to death. The punished can't re heal, and the only thing he has going for him is he's a b.a. Who refuses to lose a fight or die, but I still put my money on deadpool.
if deadpool could defeat taskmaster por using dance moves then yeah deadpool would win against the punisher plus the healing factor that deadpool has where if a body part gets cut off he can simply put it back