Well, he fought the Iron Man of the future once, and completely destroyed him. He even fought him another time - don't remember if this last fight was in continuity - and, again, totally humiliated him.
Iron Man himself stated he was no match for Spider-Man.
Tony Stark, now that's something else. Normal fight, normal conditions : Tony all the way. Very angry Spider-Man using his brain : Spider-Man has a good chance.