Shawn. The very first thought that came to my head here is Benoit will not beat Shawn in the end. he might go ahead, he might even dominate most of the match, but Benoit will lose in the end. Benoit is a guy that manages to get closer than anyone else but never being able to win the big one (other than one time).
By the one time, do you mean Wrestlemania XX - the "Greatest Stage of Them All?" or do you mean Backlash, the following Pay per view, where the exact same match happened. Because either way, Benoit won. Shawn Michaels didn't.
I think people have held onto the whole "Benoit can't win the big one" thing a bit too long. He's won at Wrestlemania. He's won in the Main Event of Wrestlemania. He's defeated Triple H and Shawn Michaels, back-to-back and in single's matches. He's defeated Triple H in an Iron Man match.
Finally, hes undefeated in Iron Man matches. And by undefeated, I mean he's won both. Not won one and tied in the other. So I'm quite sure Chris Benoit can not just handle his own against Shawn Michaels, but he can "win another big one."
Shawn is at his best on the big stage, and this certainly would be one of those.
You say he's at his best on the big stage, but being at your best doesn't mean you're leaving with a victory. He's lost more Wrestlemania matches than he's won. But more so, lets look closer at these wins and losses, shall we? (I'll only keep in his single's matches, and discount the tag ones - since this isn't a tag match, and he wasn't exactly a star in the Rockers.)
Wins:
1. Wrestlemania VIII: Tito Santana: This match was defining for Shawn's singles career, and Tito was an above average single's, mid-card, Wrestler.. about 3 years prior to this match. So while it was a defining moment in HBK's beginning singles career - it was hardly a challenge.
2. Wrestlemania XII: Bret Hart: This, to me, was his greatest victory and to add onto it, it was an Iron Man match. That adds more value in comparison to what we're discussing here. But there was a slight problem with this situation..
Shawn had to go to Overtime, in One Hour, to get a victory. 30 minutes and no pinfalls or scores I can understand - but a full hour? If Shawn Michaels is as great as he's foreseen then he is should be able to capitalize on an older, slower Hitman within an hour.
3. Wrestlemania XIX: Chris Jericho: In his return to Wrestlemania, he defeated the wannabe Shawn Michaels. It was a great match, but this was more of a re-defining moment for Shawn's resurgence of his career.
4. Wrestlemania XXII: Vince McMahon: Do I even have to? Lets just say, if he would've lost to McMahon.. then there shouldn't even be a discussion on whether he deserves to win against Benoit.
5. Wrestlemania XXIV: Ric Flair: Flair was retiring and in a relative "no-win" situation. While I'm sure he could have, the fact remains a 50 year old man took Shawn Michaels to his very limits. Benoit isn't 50, and knows how to do more damage than Flair.
Losses:
1. Wrestlemania IX: Tatanka: Albeit a countout victory, the fact that Shawn Michaels couldn't put away Tatanka, is shameful. What the hell did Tatanka ever even do? An undefeated streak? Sure.. but everyone starts out with one more or less.
2. Wrestlemania X: Razor Ramon: Shawn's first "big moment" in Wrestlemania history.. and he chokes/loses. Nothing more needs to be said.
3. Wrestlemania XI: Diesel: Shawn's first "Main Event moment" in Wrestlemania history.. and he chokes/loses. Nothing more needs to be said.
4. Wrestlemania XIV: Steve Austin: This one I'll be willing to forget, considering HBK fucking tore his back up and still went out to put Austin over. But a loss is a loss, and thats the overall point.
5. Wrestlemania XX: Chris Benoit: The shear fact that Benoit holds a victory over Shawn Michaels in a match, on the greatest stage of them all, speaks volumes for your theory that HBK > Benoit in big stage moments.
6. Wrestlemania XXI: Kurt Angle: Benoit and Angle are very similar in styles and technical abilities. Angle tore Shawn apart, and at the end of the match Michaels was lucky to have only lost.
7. Wrestlemania XXIII: John Cena: Cena was the bigger name, and Shawn couldn't out-do that in another big moment loss.
8. Wrestlemania XXV: The Undertaker: See Cena reference.
Shawn wins, but he can barely move afterwards.
On the otherhand.. Shawn loses.. and should lose, by a large number.