WWE Championship Match – King of the Ring 2002 on June 23
This match was unarguably the most contentious bout in the Triple H vs. Undertaker series. The pair were engaged in a very intense feud before the match as The Deadman had cost The Game his WWE Championship against Hulk Hogan at Backlash.
Undertaker dropped Triple H with Snakes Eyes on an exposed turnbuckle to gain advantage. But, The Rock had other ideas to spoil both Triple H and Undertaker's turbulent plans. The Phenom, however, delivered a low blow for the win.
Singles Match – Insurrextion on May 4, 2002
This was the main event of WWE Insurrextion 2002 and it was an intense battle in which Undertaker and Triple H took each other to their limits in order to determine who was The Attitude Era's most dominant competitor. Both the superstars responded to the each and every move with their own. For every Pedigree attempt, there was a Chokeslam waiting to happen and likewise for every submission hold there was a hard-hitting suplex lined up.
In the end it was The Game who secured the three-count over The Phenom inside the Wembley Arena in London.
No Holds Barred Match – WrestleMania X-Seven on April 1, 2001
This match was arguably Undertaker and Triple H's most grueling bout. The fight took place both inside and outside the ring.
In the opening minutes Triple H was sent through an announce table by way of a hard right from The Phenom. From there, the pair took the fight to the crowd and later traded chair shots, flying elbow drops and a Chokeslam to hell.
In the end they brought the fight back to the ring where Undertaker delivered a Last Ride to earn a pin fall win.
No Holds Barred Match – WrestleMania 27 on April 3, 2011
This match was the first of the back-to-back Wrestlemania matches and it was Triple H's response to Taker retiring his best friend Shawn Michaels the previous year.
Right from the word go, Triple H and Undertaker collided with some hard strikes to each other. After a battle for more than thirty minutes, The Phenom won the match in the end, but it was The Cerebral Assassin who was the last man standing. So, the two met again next year.
"End of an Era" Hell in a Cell Match – WrestleMania 28 on April 1, 2012
This was the the rematch from Wrestlemania 27, but there was a new twist to it as Shawn Michaels was announced as the guest referee for the match.
Triple H and Undertaker took center stage with Taker's Wrestlemania streak on the line. Never mind The Streak and the pinfall, this emotional rollercoaster of a match perfectly showed the well-established timeline that prefaced this moment.
After multiple chokeslams, pedigrees, tombstones, last rides and sweet chin musics, the Undertaker kept his streak intact in the end as the three veterans of pro-wrestling helped each other out of the ring.