To me, this is, if nothing else, the most noteworthy of the first round match-ups. It's a battle of the WWE's Greatest Giants. The past -vs- the....also sorta past but hey, it's OK cause he's a Deadman.
I understand that, in his prime, Andre was very quick and agile, even able to throw a dropkick. But I also understand his agility and such became extremely limited as his career progressed. The Undertaker, while age has certainly hampered him, has retained the ability to still put on damn good matches with the right people. Even close to fifty, with all the injuries he's had, he's still able to walk the top rope and do a damn good looking tope.
I feel Taker was also able to adapt to more styles and tell better stories in the ring. Andre played the role of "pissed off giant" to perfection but, aside from that, what else did he really ever have the chance to do? Undertaker not only mastered that role (or an incarnation of it as the no-selling deadman at the beginning of his run) but he was also able to show weakness with his later characters. Taker's managed to have great matches with good to great workers and even, to a degree, drag some pretty bad wrestlers to watchable matches. In ring ability I'm going to give to Undertaker.
Taker hasn't been given the chance to cut good promos much during his career but, when he has, he's always delivered (his Big Evil run is a personal favorite of mine). The great he's done far outweighs the bad choppy, campy, devil worshipping ones that were really just bad from the beginning as far as the scripts go. That being said - Andre was basically always half screaming-half talking in half-French. It was bad. A master promo he was not. Taker wins promo as well.
Charisma is a tough one. Both guys are such great characters in the history of wrestling that they both seem to have an aura about them no matter what. Undertaker has one of the most impressive entrances I've ever seen and, every time I've seen it, live audiences are stunned. It might sound like BS but arenas get hot as hell during live shows and, each time I've seen Taker live, the whole place seemed to cool down during his entrance. It's amazing. And Andre was, literally, the Giant, man! Most Americans had never seen anything like him and, because he traveled so much, he was always treated as a special attraction. He came to town once in a great while and it was a big deal. I'm going to brazenly call this one a draw.
Andre wins draw hands down. Undertaker has been a main eventer for his entire run in the WWE but it's only been the last few years where his appearences usually mean something. WWE has only recently started treating Taker like the special attraction that Andre was for almost his entire career.
And Undertaker wins accomplishments hands down. His WrestleMania streak alone is more impressive than any accomplishment Andre can legitimately hold claim to.
I'm calling this one for Taker.
