6. Worst: The Undertaker Vs. Mr. McMahon – 2003
The chairman of the board, Mr. McMahon, continuously made Undertaker’s life a misery by costing him the WWE Championship at No Mercy 2003. Undertaker clashed with Brock Lesnar in a Biker Chain match for the WWE Title, and McMahon halted Undertaker from winning the title. Nevertheless, Undertaker defeated Brock Lesnar and Big Show in a handicap match, where he earned the right to pick his opponent. Many thought that he’d opt to compete for the WWE Championship again, but McMahon taunted him, and he announced that he’d face McMahon in a Buried Alive match at Survivor Series 2003.
Undertaker dominated the bout as expected, and McMahon was bleeding profusely. He carried McMahon to the gravesite, but there was an explosion. His brother, Kane, interfered, aiding McMahon in defeating Undertaker. This match was significant as it was Undertaker’s final match as the American Badass returning as the Deadman at WrestleMania 20.