The Big Bossman VS Mr. Fuji
Mr. Fuji actually has more titles than Bossman does, believe it or not. Bossman was the type of dude who would always get so close but the heel would lose by DQ to keep his title. Fuji, on the other hand, won the WWF Tag Team titles five times. He's also a Hall Of Famer and The Big Bossman, in spite of being iconic, is not. All that being said, however, there's not a planet in this solar system where Bossman doesn't drop Fuji like a bad habit in this match. Dude be servin' hard times.
"Cowboy" James Storm VS "The Franchise Shane Douglas
This is going to be controversial, but I'm going with James Storm here. I've seen both wrestler during their primes, and he just seems more consistently impressive to me. Yes, Shane Douglas is far more decorated. He is a four time ECW World Champ, a two time ECW TV Champ, an NWA World Champ, a UWF TV Champ, a WCW US Champ, a two time WCW Tag Team Champ, and an Intercontinental Champ (which he held for a grand total of less than 15 minutes, but still). Storm is a one time TNA World Champion, but only held the belt for one week. But he beat Kurt Angle to do it, so...wash? He's also a 12-time Tag Team Champion, and one of only two full time wrestlers to be with the company for the entire run of its existence (the other man being AJ Styles. Jeff Jarrett hasn't wrestled in two years, so...fuck. Can't figure out how to onomatopoeiaize the sound of a razzberry. Sure, I can type the word razzerry, but it's just not the same thing; it doesn't have the same effect. I dunno...Wait. What was I talking about?) Anyway, my contention is that James Storm may have the slightly less impressive resume, but in this case the in-ring ability doesn't match the title history of the two men. (Not that Shane Douglas wasn't good in his own right. He got the name "Franchise" because he was one of the most important wrestlers ECW ever had.) And make no mistake, I'd LOVE to see these two go when Douglas was in his prime. It would have been one for the ages. But I think even then, Storm is just that much better. Cowboy in 22:28.
Akio Sato VS "The Natural" Butch Reed
Reed would tear through this half of The Orient Express like a "Hacksaw".
Damien Sandow VS Trevor Murdoch
Sandow gave John Cena a helluva match a few weeks ago, and the biggest thing Trevor Murdoch ever did was hold onto the tag team championships when there were no contenders. Damien Sandow in six. (You're welcome!)
Floyd "Money" Mayweather VS Evad Sullivan
I don't believe I'm doing this, but I'm going with Mayweather. Evad Sullivan (his name is Dave, but he was dyslexic; dammit, WCW...) was never very good, so I imagine "Money" could actually beat the man without too many shenanigans.
Big Vito VS Goldberg
SPEAR! SPEAR! GOOD GOD, KING! SPEAR! (I think something else happens after that, but you get the point.)
JTG VS "The Polish Hammer" Ivan Putski
JTG is still (somehow) employed by WWE, despite not being on a TV program for the last year, and sporadically for the last five before that. Ivan Putski had a long-standing feud with "Superstar" Billy Graham when he was WWWF Champion. If he can find the sonofabitch, one quick Polish Hammer to the chest is all he'll need to advance.
Air Paris VS "The Belfast Bruiser" Fit Finlay
I'd like to think this match would go something like this: Paris tries to hit Finlay as he's getting into the ring with some flippity-flip top rope move and the Irishman counters by swatting him out of the air with his shillelagh. Bell rings to start the match, Finlay pitches the stick, goes for the cover and gets the pin. Because his Airness signed a release form, Finlay is not held liable for the in-ring death. The end.
The Big Bossman defeats Mr. Fuji
"Cowboy" James Storm defeats "The Franchise" Shane Douglas
"The Natural" Butch Reed defeats Akio Sato
Damien Sandow defeats Trevor Murdoch
Floyd Mayweather defeats Evad Sullivan
Goldberg defeats Big Vito
Ivan Putski defeats JTG
Fit Finlay defeats Air Paris
Come on back for brackets XXIX!