Ancalagon the Black vs Sauron

Match between two of Melkor's greatest servants

Battle takes place in Thangorodrim

How does this go?

Sauron wins.

The dragon in an outright confrontation.

Based on?

Based on the Dragons were basically created for such a thing.

And I am basing this off of just dropping these two down in an arena with no prep or anything like that.

The majority of things Sauron has accomplished has been through machinations and plotting. Very rarely has he appeared and just been a devastating powerhouse. He was ultimately defeated by two elf lords in a mainly physical match( though they also died). And I simply see the dragons as the most physically imposing beings in all of middle earths history besides the stone/storm giants. One blast from this dragon and the only thing left will be the one ring.

That being said, the dragon may have no way of permanently putting Sauron down, but he should win a direct confrontation such as this quite easily.

And before people come in with the name calling and overly long explanations, this is simply my opinion on the matter. Yes, I have read all of the books and no, I have not spent months and months trying to analyze every word in them.

Sauron was just never as impressive as he was made out to be.

Well Sauron did solo Minas Tirith and crushstomp one of the most powerful Elf Lords in a magical contest and (to some extent) tanked Luthien, who was able to mind**** Angbad to sleep

He's also more powerful than Osse who can casually move small countries around with his magic and than Elf Lords who can effortlessly bust up fortresses. keeping in mind Gil Galad is one of the most powerful Elf Lords and Elendil is on par with him (as well as being the father of a dude who cursed an entire kingdom of men to be ghosts indefinitely)

Outclassed, Sauron is not

Sauron could ward off the power of the Valar sent to destroy Numenor, alone and unaided.

He probably wins.

He didn't ward it off he barely survived it. That being said is Sauron allowed to use his Maiar powers or does he have his ring?

I would assume, in absence of any stipulations, Sauron has his One Ring, since that's the peak of his personal power.

Then I say Souron due to superior manipulation, creation and magic feats and also his ring being indestructible to Anc's fire.