Triple H and The Undertaker are two of the biggest stars in WWE history. Combined they have held 21 World Championships and have battled the greats at countless Wrestlemania events. The Undertaker had the greatest streak in wrestling history, when he went 21-0 at Wrestlemania 29 by defeating CM Punk.
Triple H dominated the main event scene on Raw in the mid 2000s. As the leader of Evolution, he kept hold of his World Heavyweight Championship as much as he could, and made huge stars out of teammates Randy Orton and Batista. He had a reputation of politicking to keep himself in the main event and refusing to put over young stars, although that has gone away in recent years due to his work with NXT.
The Undertaker and Triple H have a long and storied history together. They battled a record three times at Wrestlemania – more than any other pair of opponents – although The Undertaker picked up the win in all three matches (Wrestlemania X7, 27 & 28). Triple H really got one over on The Deadman, with a shockingly low number of wins in singles competition against The Phenom.
Times Triple H Beat The Undertaker
Despite wrestling each other for over 20 years, Triple H only beat The Undertaker 5 times in singles competition. For somebody who is famous for wanting to win as much as possible and politicking to keep himself on top, it’s a shock to see him have such a miserable record against another WWE legend.
The five times that Triple H has beaten The Undertaker are;
WWF Shotgun Saturday Night
Feb 8th 1997
Hunter Hearst Helmsley (c) def. (DQ) The Undertaker
WWF Smackdown! Taping
Jul 11th 2000
Triple H def. (pin) The Undertaker
WWF Insurrextion ’02
May 4th 2002
Triple H def. (pin) The Undertaker
WWE Monday Night Raw
Aug 26th 2002
Triple H def. (pin) The Undertaker
WWE Super-Show Down
October 6th 2018
Triple H def. (pin) The Undertaker
The Game did manage some more wins in multi-man matches. He and Shawn Michaels triumphed at Crown Jewel 2018 as D-Generation X faced Kane and The Undertaker (The Brothers of Destruction). This was Shawn Michaels’ last match, although it was one of the worst WWE matches of all time.
Now both Triple H and The Undertaker, there is no chance of The Game increasing his record over The Deadman. However, the two will go down as two of the all-time greats and deserve to headline their own classes in the WWE Hall of Fame (The Undertaker did so in 2022).