2. The Undertaker vs. Brock Lesnar (WrestleMania XXX)
Surprise! This entry will do bout shock a lot of fans, and might even anger others, but there will be a lot of readers who agree somewhat with what is being proposed here. The Undertaker's vaunted winning streak at WrestleMania was priceless to WWE, perhaps even more valuable than a World Title match on the show each year. Nobody can deny the fact that it would have been The Undertaker who made the decision to lose at 'Mania XXX - Vince McMahon likely trusted the man's judgement enough to make the call for himself, and choose who he was going to stare at the lights for. Nonetheless, it came completely out of the blue, nobody expected it, despite what many have claimed. The match was fine, a truly exciting example of how powerful the streak was, but the ending completely deflated absolutely everyone. Paul Heyman has described in interviews since how the air was sucked out of the building when the referee made the count, and whilst it's up for debate whether or not it was the right call, it did suck to watch such a record come to an end.