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LunaticFringe wrote:

I’d put my money on Gandalf in the fight, for a couple of specific reasons:

First, consider the fact that, when asked originally by Manwe to go to Middle Earth, Olorin wished to stay in Valinor. He felt doubt in his stregnth to match Sauron, and relented only because of Manwe’s faith in his purpose. As Gandalf, he sets aside that doubt, and for good reason, because of the faith Manwe had in him, and never questions his purpose again.

We see this faith rewarded in a number of forms; when Gandalf goes into the realm of the Necromancer alone, proving once and for all that Sauron had again taken physical form. For one whom does not believe himself strong enough to take on a Maiar of a higher order, his going there is akin to suicidal. And yet he does, knowing that it is the only way to continue his task.

We see this again when he challenges the Balrog in Moria; while both are Maiar, one could honestly state that Gandalf is the true underdog. The Balrog sacrificed his form for the powers of fear and death. Olorin sacrificed both his form, and a majority of his power to fulfill a task that did not require him to defeat this foe. Compare the weakening of Saruman after the destruction of his staff to that of Gandalf. Certainly Saruman had already fallen far with his dedication to finding the ring and the loss of his will, and therefore, his power, in bringing forward his search. But it is plain that Saruman could not have challenged the Balrog for 11 days on the Pinnacle without rest as did Gandalf without his staff. His manner of focii was gone, and the majority of his overt power was still absent, and yet Gandalf defeated a deadlier foe almost purely by the stregnth of his will to continue the fight.

We must also consider Sauron’s own history in battle. When he has gone out in force, both with Melkor, and on his own, it has given rise to his defeat. Sauron knew this, else he would have challenged the Host of the West himself at Morannon. He was of body, and of great stregnth and stature during the period of the War of the Ring, but chose to remain at Barad-Dur. And no, it’s not because he was just some eye in a tower. He held the same doubt in his soul that he would again fail without having the One Ring on his finger as he had the last time, and may even still. A fallen foe had destroyed his conquest before, and he would not have it broken again. As said during the parley and in the last debate, Sauron could only send forth his legions to crush the host- he could not chance to do it himself. His doubt had overcome him to work on his own behalf, and his lack of knowledge as to the true means of his defeat would undo him.

When you think about it, each time Sauron was defeated, it came because his hand was forced. The Last Alliance made him break their seige to his undoing. The Host of the West assaulted him to give the hobbits time to covertly come to Mount Doom. What Sauron never picked up on was that you don’t always have to call the bluff when it’s shown. He would have been a pathetic poker player on a table with equals because he was not able to concede the present as an investment for the future. He threw his armies at Minas Tirith because Aragorn revealed himself, and failed because his attack was not fully prepared. He lost the War because he played into a trap while thinking it was his that had sprung.

One last thing to consider is that Sauron had never been challenged, let alone bested, by one of his stature. He’d fallen to men and elves, but he had never faced off with another Maiar; as it were, those scared him greatly, given his refusal to challenge Aragorn when he had the opportunity. For Gandalf the White, it was a "been there, done that" situation, and he was wearing the t-shirt to prove it, with every bit of the power that he had sacrificed to come to Middle Earth along with him for the final showdown. Sauron is afraid to come out and play with a man carrying nothing more than a sword; a being completely and totally beneath his stature. He doesn’t want to come out and mess with the chosen champion of the Valar. Gandalf isn’t allowed to challenge Sauron because the free peoples would think him a god; not because he can’t kick his ass. For those reasons above, had Sauron come out to play and went toe to toe with Gandalf, I believe that he would have matched him blow for blow until the destruction of the One. Not because he did not have the stregnth to destroy him overtly, but because of the role that he was sent to fulfill, by Illuvitar through Manwe. Sauron’s very nature gave Gandalf the means to defeat him, but the manner with which the history of Middle Earth had already been plotted set the limit on his ability to defeat his foe, not the ordaining of the Valar.

I tend to believe that Olorin was sent by Manwe himself as an insurance policy. Something in his heart gave Manwe the thought that if any of the chosen Istari would fulfill their goal, it would be him. He was given the full reign of his power in his return because he had sacrificed himself in lesser form in need to continue his mission. Gandalf suceeded in the quest to negate Sauron because he would not believe otherwise; so long as he stood in direct opposition to the dark lord, the peoples of Middle Earth could not fail. And in the form with which he was sent back, not even Sauron himself could challenge him directly and succeed. Gandalf always maintained hope, even when there was no further reason to do so; even at the Black Gate he had not the capacity to despair. When shown the mithril coat, he challenged. The free peoples succeeded because he would not let them fail. It’s the bending of Illuvitar’s melody to overcome that of Melkor in the song of the world; the lesser chorus overcomes the loud bark of discord. Gandalf’s part was to lead that chorus of sound as a walking instrument during that time as the history of the world had been written in note.

Summary:

Gandalf v. Sauron in Middle Earth: tie.
Gandalf v. Sauron anywhere else: Gandalf via KO.