This match has "replay of Wrestlemania 13" written all over it. Flair locks on the Figure Four, and Austin refuses to tap out, eventually passing out from the pain. Both men covered in blood.
Very close match, kayfabe wise. I think Flair has the advantage because while both guys rarely lost, Austin still lost more often.
Historically, I think it's a virtual dead heat, with a slight advantage to Austin do to his being the forerunner of the uberpopular Attitude Era. Ric Flair cut a better promo and was a better worker.
My vote goes to Ric Flair, but very narrowly.
Replay of Mania 13?...huh? The submission match at Mania 13 was great because you had two of the most aggressive men in the history of pro wrestling beating the absolute hell out of one another. Flair wasn't the aggressive type. He was clever, sneaky and cruel, but he wasn't Bret Hart. Bret Hart was far more aggressive, and intense, than Flair ever was. Austin didn't just pass out due to being in the sharpshooter, he passed out because they beat the hell out of each other for about 20 minutes. Flair doesn't bring that kind of intensity to the table.
I'm not buying into the "Austin lost more often" argument. Flair lost A LOT over the years, and he could, because he was a top heel. Maybe I'm wrong, but I need to see proof to believe that.
I agree Flair was probably the better worker, but not by much. He put on longer matches, for a lot of years, with some really talented guys (Terry Funk, Steamboat, Dusty Rhodes, etc.). I think Austins in-ring ability has been trashed in this tournament, and I'm not sure why. The guy was a GREAT worker before Owen broke his neck, and was above average after.
But mic skills? Austin gets the edge there. Austin was golden on the mic, as was Flair. But Stone Cold was the best "character" of the 90's. While his character always stayed the same, he had great range. He could make you laugh, pump you up, or make you cringe. The guy could do it all. As a heel, there has never been a better talker than Flair, I'll give you that. But as a face, Flair was nothing special on the mic, minus stripping down to his boxers.