Jackie Fargo VS Hardcore Holly
Hardcore may live up to his name and all, but Jackie Fargo (according to Jim Cornette) invented the whole using tables and chairs thing in professional wrestling. (And the strut, as variated by Ric Flair and Jeff Jarrett.) Fargo wins.
Triple H VS Terry Taylor
Red Rooster=Dead Rooster. Game [goes] over.
Monty Brown VS "Wildfire" Tommy Rich
Originally, I was gonna put over Wildfire because he was NWA Champion back in the early 80's, when that sort of thing was hard to do, but then I read his Wikipedia entry. He was champion for four days, and only because of politics. Harley Race helped out Jim Barnett by letting someone from his territory to win it. Take that away, and you've got a decent career, but no match for Monty Brown's athleticism. He may not have been a good technical wrestler, but his power game was ferocious. And he was a perennial bridesmade to whoever the TNA World Champion was for two straight years. All main event. Gotta go with the Alpha Male on this one. Feel the...POOOOOOOOUUUUUUNNNCCCCCEEE-UH!!!!
Chris Benoit VS "The British Bulldog" Davey Boy Smith
Now this would've been a helluva match. Chris Benoit grew up idolizing Dynamite Kid, and Davey Boy not only tagged with him for 12 years, but was Dynamite Kid's younger cousin. (What's even weirder, Benoit and Davey Boy were in a car crash together in 1989, on their way to a show in Canada.) Their styles are similar, their in-ring pedigrees second to none...this would've been a 5-Star on the Meltzer scale. I have to give the win to Benoit, though. He's got a more well-rounded move set and he's won the main event of Wrestlemania (though it's been redacted from WWE History because of what he did a few years later; and rightly so).
Jackie Fargo defeats Hardcore Holly
Triple H defeats Terry Taylor
Monty Brown defeats Tommy Rich
Chris Benoit defeats Davey Boy Smith
Come on back for Bracket VI!