#1 The Undertaker has never pinned Mr. McMahon
In the ongoing WWE Network documentary "Undertaker The Last Ride", the cameras have shown the immense respect and care that The Deadman and his boss, Vince McMahon have for each other. The Undertaker mentions in the documentary that Vince is like a father figure and a brother to him and said the following.
"I can’t think of anybody more influential in my life, other than my father, than Vince. I love Vince to death. I would take a bullet for the man, honestly.”
But on-screen, Mr. McMahon and The Undertaker have had many memorable rivalries, matches, and moments against each other. Surprisingly, The Deadman has never been able to defeat his boss in any of their matches.
The two famously fought each other in a Buried Alive match at Survivor Series 2003, but Kane interrupted in that match to help Vince bury The Deadman in dirt and win the match. The two also took on each other on RAW in May 1999, but this time as well it was the evil McMahon who won by disqualification after 'Taker shoved the referee.