I know that hindsight is 2020 and all, but what big money match do you recall being totally in the dark about the winner at the time, but in retrospect, it seems so obvious as to who was going over?

I would say Hogan vs. Warrior. I remember the much younger version of me could’ve seen it going either way, but when I look back, it is obvious that the whole point was Warrior going over for the whole passing of the torch thing, which, well, didn’t go so swimmingly. 
I knew Warrior was going over even at the time.  To me that was obvious. 
For me it’s gotta be Bret vs Bulldog.  I mean of course Bulldog was winning, but at the time I wouldn’t have been shocked if they went either way with it.  In fact I thought Bret couldn’t lose because then he would have to be going to WCW and I couldn’t see that happening.