Beat both times
As Gurthang pointed out Gandalf being an "Istari" limitted his powers. So there Sauron had him beat.
Olorin was said to be the wisest of the Maia, but wisest isnt always the powerfullest. Sauron again as a Maia was more powerful then Gandalf (Olorin), there were a handful of Maia more powerful then Sauron, I will have to get it specifically who, but I do know there were 6-7 equal or greater Maia then Sauron,
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