Jeff Hardy winning his first WWE Championship @ Armageddon 2008 was pretty shocking...he was in there with 2 guys with multiple WWE & WHC titles in Triple H and Edge in a triple threat. It was REALLY surprising that Triple H allowed himself to be the one pinned and put Hardy over IMHO. Classy move on the part of The Game.
RVD defeating Cena at ECW One Night Stand 2006 for the WWE Championship also springs to mind. Cena was only a little over a year into playing the role of SuperCena and overcoming the odds every time, so it was quite a shock when they put RVD over. I can only imagine how his reign would've played out if not for that one stupid mistake that cost him it and the ECW Championship.
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