Sauron vs Olorin 1on1

[Galorme]

Good point. They were not roughly equal in power at the start, but they both took significant blows to the power available to them. If you take Sauron as being the entity contained in the Eye (or whatever his physical form was) at the end of the third age I doubt he would be able to stand up to much. But if you take it as Sauron, the dispersed and hugely potent being that inhibits the ring, the tower, and the entire mass of orcs etc then it would be hugely powerful. If you take Olorin as being the being contained and restricted inside the body of Gandalf then he would also be, if not weak, not too strong by Maia standards. If you took him as the powerful wise being that lay in wait inside of the old man then he is also hugely powerful. So it depends, with restrictions probably Gandalf, without probably Sauron.