1. The Undertaker
https://www.youtube.com/watch?v=ySZHmuGhwjk
On November 16, 2003 at the WWE Survivor Series 2003 PPV, The Undertaker challenged Mr. McMahon to a ‘Buried Alive’ match, after winning the right to choose his own Survivor Series opponent and the stipulation, on an episode of SmackDown!.
During the entire match Vince took a beating from the Deadman and had hardly any offense at all.
11 minutes into the match, Undertaker’s evil brother Kane interfered into the match, attacked his (kayfabe) brother and buried him alive, thus enabling Mr. McMahon to win the match.
Who would have ever thought in 1991 or 1992, that Taker would one day lose to Vince McMahon.
What an upset!!
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