5. Triple H
The next year, at Wrestlemania 27 The Undertaker faced off against Michaels’ best friend Triple H in a No Holds Barred match, it was a high voltage encounter with Triple H coming inches short at conquering the streak. Triple H delivered three pedigrees and a Tombstone but Taker kicked out of all of them.
At one point, Undertaker delivered a devastating Tombstone but The Cerebral Assassin kicked out of it leaving The Undertaker shocked. During the finish, Triple H grabbed a sledgehammer but Taker applied the Hell’s Gate to which Triple H had to submit thus making it 19-0 for The Undertaker.
Undertaker could barely walk after the bout, he was helped by the WWE medical staff who took him backstage.
Next year at Wrestlemania 28, Triple H faced The Undertaker in a rematch but in a Hell in a Cell match with Shawn Michaels as the special guest referee, amidst the match Triple H delivered two pedigrees and Michaels delivered a Sweet Chin Music but Taker kicked out and executed a Tombstone which Triple H powered out. However Taker delivered another Tombstone to win the match and extend the streak to 20-0.