Jim Londos VS "The Nature Boy" Ric Flair
Compare this: Ric Flair has been NWA/WCW/WWF Champion for a combined total of over 3,700 days in his lifetime. Jim Londos was World Champion for a total of 2,628 days during ONE reign. It's the second longest run as champion, and he retired with the belt. Tough to parse, but Ric Flair has a more well-rounded body of work and had to wrestle a far more diverse pool of opponents than Londos did.
"Stone Cold" Steve Austin VS Booker T
They had this fight already in a grocery store. Let's just pretend it's this match again, because it was awesome the first time, and I don't think that in a tournament setting like this Booker would go over Austin anyway.
Harley Race VS "Macho Man" Randy Savage
Harley Race may have been pimpin', but the Macho Man was the MAN. This would be an old-school wrestling fan's wet dream, though. Savage wins this clash of the ring titans.
Nigel McGuinness VS Brock Lesnar
Brock takes care not to leave Nigel in a puddle of his own blood, vomit and piss because McGuiness had his career cut criminally short by contracting hepatitis c, but nonetheless, not even a former ROH World Champion is nearly enough to withstand the onslaught of Brock Lesnar.
The Undertaker VS Andre The Giant
Many have speculated aloud what would've happened if The Phenom had ever squared off against The Eighth Wonder Of The World. Shockingly, I think The Undertaker would win. I know, it's Andre, right? In his prime (and well past it) he was un-fucking-stoppable. But so was The Undertaker, and only part of that was his character being a zombie. He's a legit 6'10" tall, and can do things most big men never dream of, like a plancha and the Old-School top rope clothesline. He wouldn't be able to chokeslam, Last Ride or Tombstone Andre, that's for damn sure (Andre wouldn't let him), so he would have to rely on high impact strikes and his submission game. After about three minutes in the Hell's Gate, Andre The Giant has no choice but to tap out.
Pat O'Connor VS George Hackenschmidt
George Hackenschmidt earned his world title, legitimately. No one can ever take that away from him. I'm still going with Pat O'Connor. We'll say...Hackenschmidt failed to train adequately for his match because he held newfangled "workers" like O'Connor in contempt, and so lost any and all endurance he may have had. This allows O'Connor to pick him apart in no time.
Kurt Angle VS Bret "The Hitman" Hart
The best wrestling match that never happened. I can't do this one justice by prattling on about how relentlessly awesome this match could've been. Two of the best wrestlers of all time, one ring, one winner. I pick Kurt Angle, because I think he is an evolution of Bret Hart; a step just above. (And hey, the Olympic Gold Medal in Men's Freestyle doesn't hurt either.)
Lou Thesz VS The Rock
...y'know what? Fuck it. The Rock wins. You can talk all you want about how amazing Lou Thesz is, but The Rock is electrifying....
"The Scissor King" Joe Stecher VS Ed "The Strangler" Lewis
These two were rivals in and out of the ring. Stecher refused to do business with The Gold Dust Trio and started his own rival promotion. He even bought out the Trio's champion Stanislaus Zbyszko just before a match where he was supposed to drop the title. In the ring, Lewis and Stecher have had...what's a word that means "beyond epic"? Insane? That fits. They had insane matches. One was two hours and only ended when Lewis was thrown from the ring on accident and landed head first on a chair. Another was a FIVE. AND A HALF. HOUR. DRAW. Lewis is the man who took the title from Stecher on two different occasions, but the second in 1928 was a business deal. I'm not really sure who would win once and for all, but I pick Joe "Scissor King" Stecher.
"Big Poppa Pump" Scott Steiner VS Frank Gotch
Frank Gotch bend Scott Steiner in half. Make him humble.
Hulk Hogan VS Shawn Michaels
I went back and forth on this one. I wanted Shawn Michaels to go over, badly, mainly on the strength of the bullshit politicking that went into the Summerslam '05 match these two had. But like I said last round, this is 80's Hogan here. Pretty much his match against Antonio Inoki in '83 sealed it for me. If Hulk could pull that kind of performance out of himself to combat the Heartbreak Kid, then he has what it takes to overcome the onslaught of one of the greatest the game ever had to offer.
Ric Flair defeats Jim Londos
Steve Austin defeats Booker T
Randy Savage defeats Harley Race
Brock Lesnar defeats Nigel McGuiness
The Undertaker defeats Andre The Giant
Pat O'Connor defeats George Hackenschmidt
Kurt Angle defeats Bret "The Hitman" Hart
The Rock defeats Lou Thez
Joe Stecher defeats Ed Lewis
Frank Gotch defeats Scott Steiner
Hulk Hogan defeats Shawn Michaels