Funk over Orndorff - "Mr. Wonderful" was pretty great, but not as great as Terry Funk. He also wrestled the business in the wrong direction (start in the WWF, go down to indies). Funk, on the other hand, payed his dues, won his titles, payed more dues, wrestled in indies... he did it all. And he did it well.
Dynamite over Hart - Well, I know it's a lost cause. Most people on these boards will say that Hart was a better worker, and one of the best of all time. I know a lot of people would disagree. Ric Flair would disagree, and tried to expose Hart as a not very interesting wrestler. I'll go with Kid here because Bret Himself has said on multiple occasions that Kid was "pound-for-pound, the greatest wrestler who ever lived".
Steamboat over Savage over Sting - I can't believe you forgot Steamboat. Maybe i'll look like an idiot if he pops up somewhere else in the brackets. Otherwise, you've just proven my point about him being completely underrated and overlooked. (Savage over sting). Savage could go for a while. A long while. Just ask Ricky Steamboat. Terry Funk also thinks Randy Savage was the first guy to ever put anyone through a table.
Malenko over Benoit - I think both guys were great wrestlers (obviously), and neither were particularly great on the mic. But Malenko was a bit better. And apparently, really funny backstage.
Hart over Angle - Angle's a great mat guy, etc. Owen could do it all, and likely would have had his career not been cut short.
Austin over Hogan - Well, I guess it takes one era-defining wrestler to eliminate another. I like Austin in all his incarnations, particularly as the last holder of the Million Dollar Belt. He could work, he could go, and he could certainly take Hogan.
HBK over Taker - Ooooh, here's a doozy. I think Taker's a good guy, but his career hasn't always been that solid. He's had some huge ups, but definitely a lot of downs in terms of wrestling ability. He often just relied on his gimmick to get over. For Michaels, I've never seen him get too lazy. He gets the win here, and revenge for a whole lot of pain caused by the dead man.
Flair over the Rock - I can't see anyone going the other way. I just can't.