I would say that if Gandalf had the chance, he would have beaten the WK. He did have a chance on Weathertop, but this was against all 9, and I can't see Gandalf doing anything except holding them off, and drawing some away like he did.
With that suspenseful scene at the Gate of Minas Tirith, if Rohan wouldn't have arrived then, and Gandalf and WK didn't just size eachother up and they fought, I would say Gandalf would have beaten the WK. However, this would go against the prophecy, so there for, the WK (maybe feeling overmatched) retreats to the battle, where he is slain by Eowyn, fulfilling the prophecy.
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