WrestleMania. The Grandest Stage of Them All. One of the most entertaining sporting events every year, the show draws millions of viewers and dollars annually, making it a must-see for all fans.

Of course, WrestleMania isn’t possible without elite Superstars, great bookings, and entertaining matches. Luckily for WWE, Triple H, one of the most iconic stars of the company, has taken part in 19 matches at the big event.

He did not face off against The Rock (in a singles match), Hulk Hogan, Steve Austin or Bret Hart, but that doesn’t matter. His social media says he does “What’s best for business,” and he’s been able to do just that, no matter who he has faced. Triple H is one of the greatest performers in the history of wrestling.

He’s always saved his best in-ring performances for the biggest wrestling event in the world, every single year.

As such, he’s earned a ton of love and respect from fans. He’s faced so many legends, and it’s safe to say he’s still got a few great shows left in him. Though it’s hard to believe his upcoming battle against Roman Reigns will be his best, it will without a doubt be memorable.

Everyone hopes that these two can live up to past Triple H matches, but that’s easier said than done. No matter how it turns out, we’ve still been lucky to see a boatload of terrific matches from The Game.

It’s time to look back at how his previous WrestleMania matches stack up against each other.

19. WrestleMania XII vs. The Ultimate Warrior

via wrestlingnews.co

via wrestlingnews.co

Take everything that happens in life and there’s always that one bad part you wish you could forever take away from existing.

Well, this match between Triple H and the Ultimate Warrior was one of them. The crowd in Anaheim surely did not get their money’s worth after such a disgraceful booking by the WWE writers.

It was The Ultimare Warrior’s first match in the company since 1992, which was more memorable than the match itself. It lasted less than two minutes, with Warrior no-selling Triple H’s pedigree.

18. WrestleMania XXVI vs. Sheamus 

via tjrwrestling.net

via tjrwrestling.net

Sheamus had just become one of the major faces of the company, capturing the WWE Championship just months earlier against John Cena. He become the top heel and embraced it well.

Which made sense for Triple H, one of the biggest names in WWE history, to get a match against him at WrestleMania XXVI in Phoenix. The match itself wasn’t awful, but it wasn’t spectacular either.

There were so many major events already, such as Shawn Michaels’ last ever match against The Undertaker. Triple H would put the Celtic Warrior to bed, but it wasn’t a thrilling match.

17. WrestleMania XV vs. Kane 

via smacktalks.org

via smacktalks.org

Even though this WrestleMania event was one of the best in recent memory (thanks to Stone Cold Steve Austin against The Rock for the WWE title) Triple H and Kane didn’t do a whole lot themselves.

Aside from Chyna turning her back on Kane to realign herself with Triple H, this match wasn’t anything heart-pounding. While Kane would win by DQ, The Big Red Machine would take a Pedigree onto a steel chair.

D-Generation X would re-unite once again, but that and Chyna probably were the only memorable takeaways from this match.

16. WrestleMania 13 vs. Goldust 

via fanpop.com

via fanpop.com

Looking back, part of the reason this match wasn’t that terrific was the fact that Triple H faced much more intriguing opponents in his career. But Goldust was still at the top of his game at the time.

That being said, once again, this match was average at best. There were much better matches on the card, leaving this one lost like a needle in a haystack.

Triple H would beat Goldust in a match that lasted 14 and a half minutes. Again, this match wasn’t terrible by any means, but the legend participated in much better matches at WrestleMania.

15. WrestleMania XIX vs. Booker T

via 411mania.com

via 411mania.com

When Steve Austin and The Rock face off, Hulk Hogan feuds with Mr. McMahon, and Kurt Angle takes on Brock Lesnar, it’s easy to forget that Triple H participated in a decent match.

He faced off against Booker T for the World Heavyweight Championship. There was plenty of back-and-forth momentum that brought the fans at Safeco Field to their feet.

Triple H would do what he has done so often: Retain the World Championship, much to the chagrin of fans who want to see Booker T get put over. He would put Booker T away with a Pedigree, winning a solid match that, once again, was lost in the cards of other great battles.

14. WrestleMania 21 vs. Batista

via bleacherreport.com

via bleacherreport.com

For fans like myself who grew up watching WWE in the early 2000s, this was one of the biggest matches of all-time. Looking back, it was just another way of making Batista one of the main faces of the WWE.

Batista had recently turned on his Evolution leader and mentor by challenging him for the World Heavyweight Championship. The build-up to the match was great, but Batista dominated and it was obvious he would win throughout the match.

So for that, this match is somewhere in the middle. If you hated The Game, you loved the match. But let’s be honest, this wasn’t one of the more entertaining bouts in Triple H’s WrestleMania career.

13. WrestleMania XXIV vs. John Cena and Randy Orton

via whatculture.com

via whatculture.com

Triple H faced off against two of the biggest stars in the company, who were in the midst of putting themselves on the wrestling map the way he had done ages before.

It was an overall exciting back-and-forth match between three future WWE Hall of Famers. Everybody expected Cena to win, since he was the company’s main face at the largest annual event in the industry.

Just when Triple H was about to pin Cena, Orton broke up the count with a punt and pinned Cena for the win. A fairly respectable and entertaining match.

12. WrestleMania XIV vs. Owen Hart

via heavy.com

via heavy.com

This WrestleMania was best remembered for Steve Austin beginning his first major title reign, Mike Tyson’s involvement, and the true launching of The Attitude Era. Along the way, Triple H faced off against Owen Hart.

The future Hall of Famer had a great match against a rightful WWE Hall of Famer; who saved one of his better matches for last, before his extremely tragic and untimely death a year later.

The two competed for the WWE European Championship. Despite Sgt. Slaughter’s best efforts to ruin The Game’s chances of winning, Chyna helped him overcome the distraction and he’d Pedigree Hart for the win.

11. WrestleMania 31 vs. Sting

via nerdopotamus.net

via nerdopotamus.net

This match could have been ranked much higher if the result was different. The main point was the Monday Night War coming back to life; Triple H, a long-time WWE Superstar facing off against Sting, who made his WWE debut and was WCW’s top star for years.

The best part of the match was going back in time. The original D-Generation X members came out to interfere on Triple H’s behalf, while Sting’s former rivals, the New World Order, helped him fight off DX.

Triple H would win after hitting Sting with his signature Sledgehammer weapon. WWE should have booked it for Sting to win his first match, but Triple H just HAD to win. Nonetheless, this was a great match with some shots from the past.

10. WrestleMania X-Seven vs. The Undertaker

via wwe.com

via wwe.com

When over 67,000 fans pack the Reliant Astrodome in Houston, you better hope that two of your top stars put on one entertaining and memorable match. The writers got this one right between the two WWE legends.

In an absolutely stacked card, Triple H and The Undertaker faced off in a match where it looked as though Triple H would actually end The Undertaker’s undefeated streak.

The Undertaker kicked out from a shot to the head with a sledgehammer. Of course, Undertaker was able to deliver his Last Ride finisher to pin Triple H for the victory. Undertaker’s WrestleMania record went to 9-0, just under halfway to his legendary 21.

9. WrestleMania XXV vs. Randy Orton

via cagesideseats.com

via cagesideseats.com

The milestone 25th WrestleMania outing featured two former members of Evolution going up against each other, with the pressure of putting on a match that lived up to the hype.

The Game and Orton faced off for the WWE Championship, the main event of the show. Triple H was bound to beat Orton, who, in storyline, had brutally attacked his in-law Shane and Vince McMahon, and laid hands upon his wife, Stephanie.

Triple H used his sledgehammer weapon to hit Orton, then put him away with the Pedigree to win. Without a doubt, one of the finest matches between these two men who have been involved in multiple feuds against each other.

8. WrestleMania XXX vs. Daniel Bryan

via escapistmagazine.com

via escapistmagazine.com

This match will go down as one of the best from Bryan, who had such a tremendous career in WWE and other promotions.

Bryan and Triple H faced off in the first match of the evening, with the winner getting to face Randy Orton and Batista in a Triple Threat match for the WWE World Heavyweight Championship.

Bryan would win the match, before Triple H would brutally attack him after. This set the stage for Bryan to fight back for the main event and force Batista into submission, providing one of the most epic moments in WWE history.

It wasn’t possible without this first match.

7. WrestleMania 29 vs. Brock Lesnar

via catch-arena.com

via catch-arena.com

Sorry Paul Heyman, but the man who was owned by Triple H was none other than….BRRRRRRRRRRRROCK….LESSSSSSSSSSSSSSSSSNAR!

All jokes aside, Triple H had to win this match or else he was forced to retire; so everybody knew that The Game would win. But it still needed to be performed greatly.

In the No Holds Barred match at MetLife Stadium, Triple H Pedigreed Lesnar on the steel steps to win the match and save his career. Given how Lesnar was once again a huge star in the company, the fans got the show they wanted from two big names.

6. WrestleMania XX vs. Shawn Michaels and Chris Benoit 

via officialfan.proboards.com

via officialfan.proboards.com

No matter how you feel about Chris Benoit, you can’t deny that. at the time, this was one special moment for the WWE. Benoit faced off against Triple H and Shawn Michaels for the World Heavyweight Championship.

Three big names of the company, and the heel, Triple H, appeared ready to hold onto his elusive championship once again.

In an epic finish, Benoit made Triple H tap out to win the championship. Eddie Guerrero, the WWE Champion, came out to celebrate with his buddy, making it a great Hollywood-type moment.

5. WrestleMania X8 vs. Chris Jericho

via wrestlingforum.com

via wrestlingforum.com

In my opinion, no WrestleMania had a better card than this one: Hulk Hogan vs. The Rock, Steve Austin vs. Scott Hall, and Triple H against Chris Jericho for the Undisputed Championship.

Though Jericho was raised in Canada, the Toronto crowd was cheering for The Game to steal the title away from his rival.

Despite Stephanie McMahon fighting to help Jericho win, Triple H would Pedigree her to get her out of the way. He would then Pedigree Jericho to capture the championship, ending a terrific show on an incredibly high note.

4. WrestleMania XXVII vs. The Undertaker 

via celebritypeonz.blogspot.com

via celebritypeonz.blogspot.com

This was the second time these two legends faced off on the grandest stage of them all. Triple H and the Undertaker, seemingly one last time.

A No Holds Barred Match, with Triple H getting a second chance to snap The Undertaker’s perfect WrestleMania record. In a back-and-forth match, it was clear that anyone was capable of winning this one near the end.

The Undertaker would put it away, however, as Triple H tapped out to his Hell’s Gate submission and Undertaker would move to 19-0.

Another great match between these two; but not the best.

3. WrestleMania 2000 vs. The Rock vs. Big Show vs. Mick Foley

via cagesideseats.com

via cagesideseats.com

This was considered the first main event for Triple H and it came at the Milestone WrestleMania 2000, featuring three other legends of WWE.

It was a Fatal Four-Way Elimination match for the WWE Championship. Major credit to McMahon for booking one of the greatest finishes to any WWE match ever.

Triple H would retain the title after last eliminating The Rock, arguably the company’s biggest star at the time. Even though he was already huge, Triple H would just continue to grow bigger following this one.

2. WrestleMania 22 vs. John Cena

via cagesideseats.com

via cagesideseats.com

If John Cena’s theme song lyrics were an indication of the truth, his time surely was coming. And it was at WrestleMania 22.

Though he had already found his way to the top of the card after beating JBL at the previous WrestleMania for the WWE Championship, Cenation would grow to much bigger heights after this matchup.

Cena, the WWE Champion, was able to break up a Pedigree attempt by The Game and slap on his STF submission move to force Triple H into tapping. By now, you’ve learned some of Triple H’s best matches were losses. This one was one of them.

1. WrestleMania XXVIII vs. The Undertaker

via wrestlingwithpopculture.com

via wrestlingwithpopculture.com

Part III of the great Triple H and Undertaker WrestleMania rivalry.

The Cerebral Assassin was more than determined to end the most significant streak in sports entertainment by far. Sadly for him, The Undertaker would not go down easily.

This match was so intense and filled with genuine emotion. The match was a Hell in a Cell, Triple H and The Undertaker’s signature type of bout.

With Shawn Michaels as the special guest referee, he delivered the Sweet Chin Music, which allowed Triple H to hit the Pedigree. The Undertaker still kicked out and finished off the game with a Tombstone Piledriver, going to 20-0.

How do you write a better finish than that between two legends? This was number one, without a doubt.

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