I'm honestly not sure on this match; it doesn't make sense for Undertaker to come back just to lose again. But, Undertaker has nothing to gain from beating Bray; Bray has a lot to gain from beating Taker since it would be a passing of the torch. Depends on how WWE sees it.
I'm almost 100% sure of it. Why would Calaway agree to come back just to lose?
Yes, he's the Phenom!
Taker will win.