klunderbunker, I hate you
Now that's out of the way, I'm voting Shawn here - obviously. At the end of the day, both have beaten the other. You can point to interferences allowing Shawn to gain wins, but I can point to Wrestlemania allowing The Undertaker to win. Regardless of who The Undertaker was facing, he'd win, so I don't really that them into account anymore. What I DO take into account is that Shawn was with him every step of the way, possibly doing MORE during those matches, and until the points where The Undertaker HAS to win, because his streak won't end.
Here, I'm looking at both of these men in their prime, and who I think the better wrestler is - who I think deserves to be crowned the WZ tournament champion. And that man is Shawn Michaels. The Undertaker and Shawn are gimmick opposites, almost. The Undertaker is dark, mysterious, threatening. Shawn is loud, spectacular and damaging. Shawn has, at one point or another in his career, fought in, and matched up to every opponent he's ever had in terms of their style and match type.
Using kayfabe just seems so weird here, we have to look at this deeper. Who do you prefer watching? Who do you think deserves to be the winner of this tournament? Who do we believe is the best wrestler between the 2? I answer Shawn to all those questions - he's the icon, the showstopper, the man I've spent my life watching and loving, and who has made me continue to watch the WWE all these years. He CAN defeat the Undertaker, in their primes, and you all know it.