#1 Vince buries The Undertaker
At No Mercy 2003, Vince McMahon screwed The Undertaker in his match against Brock Lesnar for the WWE title. Taker forced Vince to fight him in a Buried Alive Match at Survivor Series.
Vince came down to the ring, holding in hands together and sporting a sick smile on his face. It took a single punch for Taker to bust open Vince. For the next several minutes, The American Badass mauled the boss and proceeded to bury him in the grave that was set up near the ramp.
As Taker opened the door to the grave filling machine, it blasted, knocking him unconscious. To the astonishment of everyone inside the arena, Kane appeared and threw The Undertaker into the grave. A bloody Vince McMahon filled the grave, as Kane let out a maniacal laugh. The Undertaker, like multiple times in the past, was "killed" again.
Also read: 3 times Vince screwed wrestlers at the last moment