Chavo Guerrero Sr. (aka Chavo Classic) VS Dick The Bruiser
Dick The Bruiser would chomp Chavo Sr., Junior, or just about anybody else in the Guerrero family save for maybe Eddie. Mismatch, in my opinion, even if Chavo Classic is the oldest Cruiserweight champion in WWE History.
"Handsome" Jimmy Valiant VS Ryback
Ryback may be kind of a wuss this year, but he would bulldoze Jimmy Valliant in relatively quick fashion.
Primo Colon (aka one of Los Matadors) VS "Leaping" Lanny Poffo (aka The Genius)
In spite of holding a victory over Hulk Hogan in 1990 and being the brother of the Macho Man, Lanny Poffo was generally a manager or enhancement talent. Primo wins.
Hiro Matsuda VS The Big Show
Hiro Matsuda is the guy who trained Hulk Hogan, but he wouldn't be able to handle the "Largest Athlete In The World". Show.
Chief Wahoo McDaniel VS Earthquake
Likewise, McDaniel is a legend, but Quake is just too big an obstacle for him to surmount.
Joey Mercury VS Rasta The Voodoo Man
"Who the fuck is Rasta The Voodoo Man?" you ask? He was in the GWF for a time, then quit wrestling to become an actor, getting minor roles in "Any Given Sunday" and "Cradle 2 Tha Grave". Then he was in a wildly successful series of Reebok comercials in 2003 (which nobody remembers, but I'll take WikiPedia's word for it) then he landed what was arguably his most famous role: COLE FROM GEARS OF WAR. They had to animate the character's biceps bigger to match the voice actor, son!
Then again, as a wrestler, he never did much, and Joey Mercury was pretty damn good in his day, so I give this one to the man from MNM.
Bushwhacker Butch VS DDP (Diamond Dallas Page)
The Bushwhackers weren't much as singles competitors, and DDP won the WCW title three times, so yeah. Quick Diamond Cutter and hasta la vista.
"Macho Man" Randy Savage VS David Von Erich
David Von Erich was unfortunately the first of many (read: All but one) Von Erichs to die in a 13-year span. He was in the running to be the next NWA World Champion when he passed away in 1984, and for his family and the promotion they ran, this was the beginning of the end. Despite what he could have been however, "Macho Man" Randy Savage was all of that and more. He is one of the legends, the household names that even non-wrestling fans know about. AND he could back it up in the ring. From a skill standpoint, the guy made Hulk Hogan look like a joke. I have a feeling this guy'll go deep into the bracket, homie. OOH YEAH!
Dick The Bruiser defeats Chavo Guerrero Sr.
Ryback defeats Jimmy Valiant
Primo Colon defeats "Leaping" Lanny Poffo
The Big Show defeats Hiro Matsuda
Earthquake defeats Chief Wahoo McDaniel
Joey Mercury defeats Cole...I mean, Rasta The Voodoo Man
DDP defeats Butch
"Macho Man" Randy Savage defeats David Von Erich