41. Mr. Kennedy
Almost a year before he was supposed to be revealed as Vince McMahon’s illegitimate son (which ended up being Hornswoggle), the up and coming WWE Superstar got a DQ Victory over The Undertaker on the ‘WWE No Mercy 2006’ PPV. The very next month he did it again and defeated the Deadman in a ‘First Blood’ Match at ‘WWE Survivor Series 2006’, plus another DQ win on the January 16, 2007 Episode of Friday Night Smackdown.
That marks a total of 3 Times that he beat The Undertaker, tho non of them was a clean win.
Who knows how far this Wrestler would’ve made it, had he not been suspended as one of the first Victims of the Wellness Policy in 2007?
https://www.youtube.com/watch?v=JNzH7g2hlpk
