The Eighties
Forward Thinking Nostalgist
This angle has been a mixed bag but after last weeks amazing finale in the cage and the promo between Bray and Bryan tonight (as well as Bray's promo on the last SD), I think they are going into this match on pretty solid footing.
Bray is a a great character worker but has had very limited ring time so far, this match could be the first step in taking him up a level as more than just a mouthpiece. Bryan can have a good match with anyone and if given some time here I think he can help Bray showcase himself fantastically.
I'm not really sure who wins here, it could be closure and thus Bryan beats Bray, but I wouldn't be surprised to see Bryan lose and then win the Rumble, setting him up to face Bray at the EC to finish this feud off before moving on to the Mania build.
There is the possibility that this could all still tie into The Undertaker, but I'd say that was a 50/50 possibility at best.