Ax VS Matt Hardy
This would be an interesting clash of styles, and we could theoretically see it one day, since Demolition and Matt Hardy have both been on several Blizzard Brawl cards together (though admittedly not with both men in their prime; Ax is one of an elite group of wrestlers in history to still be active after his 67th birthday). If Ax from the late 80's tangled with Matt Hardy from the late 00's (when he was winning singles titles), who would win? I suggest Hardy, because of the singles wrestling background, and because that's as good a tie-break as any.
"Primetime" Elix Skipper VS Booker T
Elix Skipper, talented as he was, never quite got over the mid-card hump. He was also primarily a tag team guy. Booker T, though really experienced in tag teams himself, challenged for the World Heavyweight Title at Wrestlemania XIX and racked up six reigns with the thing himself. Booker spin-a-rooneys after his win in what would've been an interesting match.
Gorilla Monsoon VS Masahiro Chono
Gorilla Monsoon was a terror to behold in the ring. He routinely made life hell for Bruno Sammartino in the ring during the champ's eight year run. Masahiro Chono made his bones in Japan, trained by Lou Thez (and retiring the man in his final match in 1990), winning the NWA World Heavyweight Championship in 1992 (which was the WCW International World Title, I think? The Big Gold Belt, nonetheless), and going on to form nWo Japan. He's won five G1 Tournaments and generally goes H.A.M. in the ring. As much as I hate to say it, Chono has the stuff to beat the beloved Monsoon. But not without a fight.
Cousin Junior (aka Moondog Cujo) VS Davey Richards
"Good food, good meat, praise the Lord, let's eat." -Cousin Junior, WWF Home Video, 1986, then again after Davey Richards kicks his brains out and puts him on the mat to count the lights.
Matt Hardy defeats Ax
Booker T defeats Elix Skipper
Masahiro Chono defeats Gorilla Monsoon
Davey Richards defeats Cousin Junior
Come on back for Bracket VIII!