Triple H's Top Ten Greatest WWE Matches

A hybrid performer. A man with an old school 1960s/1970s wrestling psychology, a 1980s look, and the 1990s "attitude." Triple H really encompasses what wrestling was all about in the second half of the 20th Century.

He is the culmination of 50 years of modern professional wrestling and whether you love him or hate him the future of the industry is now, largely, in his hands.

As easy as it is to pick on "The Cerebral Assassin" over some of his life decisions and the way in which he was booked anyone who says he was handed anything obviously does not know their history.

For 20 year, Triple H has been a part of the WWE experience.  Whether he was wrestling for the WWE European Championship with Owen Hart, mocking WWE Commissioner Sgt. Slaughter with Shawn Michaels, or main eventing a WrestleMania in some of the biggest arenas across the country, Triple H has been a constant.

He is probably one of WWE's most important talents to never effectively be the face of the company.

He has always been a rung right below the true faces of WWE. However, his talent and understanding of ring psychology have always made him one their most important commodities.

"The Game" may be one of WWE's most unlikable personalities, but his wrestling ability and old school mentalities in the ring made him one of the 2000's greatest and, in a way,  most under appreciated entertainers.

Honorable Mention:

Two-Man Power Trip vs. Jericho & Benoit (WWE Raw, May 2001)

It's really depressing that one of the greatest Tag Team matches in the history of WWE ended with one of the competitors suffering the worst injury of their entire career.

Miraculously, Triple H finished the match with a quad completely torn from his bone. He even was put into the Wall of Jericho on top of the announcer's desk.

This match was wall-to-wall action and there was zero down time. Whether it was due to all four men being particularly motivated or the fact that the show was running long. It doesn't matter. This is one of the most fast paced matches any of these four men have ever had and it was just a joy to watch.

Chris Jericho and Chris Benoit won the World Tag Team Championships from the duo and unfortunately Triple H would have to sit on the sidelines for the rest of the year.

He would not return until January of 2002 in which he would win the Royal Rumble match.

Also Considered for Triple H's Pro Wrestling Countdown:

  • Triple H vs. The Rock (SummerSlam 1998): This match gets a lot of attention among lists online, however compared to other encounters these two had later on this one looks a little duller in comparison. It was still a wonderful midcard match. These two helped one another get over and a year or two later later they would both be main eventing shows together.
  • Triple H vs. Chris Jericho (Fully Loaded 2000): I have a great fondness for this match and I think it's one of the best matches of Chris Jericho's career, but even still it doesn't quite mean as much to the career of Triple H. This is still a great match. Triple H was one of the first guys to make "Y2J" look like a star.
  • Triple H vs. Chris Benoit (No Mercy 2000): A seriously underrated match from the string of matches that Triple H had in 2000 and 2001. He was on a roll and this was a gem among all of the other iconic matches he had at the time.

10. Triple H  vs. John Cena (WrestleMania 22)

I thought these two would have a slow and clunky main event, but they really surpassed my expectations and ended WrestleMania 22 right.

I also think, historically, this was a big night for both Triple H and John Cena. Triple H had dominated the main even scene for almost four years  when he was finally sent away by his former Evolution cohort, Batista. When Triple H returned Batista had been shipped to Smackdown! and in his place was the new face of Monday Night Raw - WWE Champion John Cena.

These two had to butt heads at some point and it came to ahead in Chicago's Allstate Arena. The man who once ruled over the World Heavyweight Championship on Raw with an iron fist challenged the young WWE Champion for the "throne."

It was the story of the old lion battling the new lion.

It was a great story this match told, one that we could never likely see told again. John Cena was walking in as the underdog champion. He was facing the man who had largely ruled the roost of the WWE for the past three years.

Triple H was the first man to wrestle John Cena at WrestleMania and have a good match with him. Cena was still coming into his own as a "technician" in the ring and being in the main event with a guy like "The Game" was a wise move for his first headlining spot at the biggest show of the year.

The beginning of the match effectively established that John Cena could not match Triple H's wrestling ability and when he came back to win through sheer guts and determination it sold him as a champion even more so.

At the time it felt like the company was shoving the young Cena down our throats  but looking back 2006, and this match in particular, were pivotal in establishing Cena as the main event player he is now.

9. Triple H vs. Jeff Hardy (No Mercy 2008)

The final No Mercy event was a great one in terms of main event  matches.

Honestly, I think Jeff Hardy got more out of losing this match than John Cena did winning his match with Triple H at WrestleMania 22.

Hardy returned to the WWE in the Summer of 2006 and began building momentum, moving up the card, and drawling larger and louder crowd reactions each passing month.

By early 2008 it couldn't be ignored any longer, Jeff Hardy was main event material. After a few speed bumps, Hardy recovered and found himself headlining pay-per-view events for the first time - with Triple H.

These two had several notable television matches  in the early 2000s, but now Hardy, while still the underdog, was on a more level playing field with one of the most consistent performers of the last decade.

If "The Charasmatic Enigma's" match with The Undertaker in 2002 was a sign that he could be somebody in the world of professional wrestling than his WWE No Mercy match was proof that he was.

Hardy was unable to "grab the brass ring" on this night as "The Game" retained the WWE Championship after rolling up Hardy after he hit the Swanton Bomb.

This loss wouldn't kill any of Hardy's momentum as he went on to win the title later that year. Triple H  definitely helped legitimize Hardy as he acceded into the main event scene.

8. Triple H vs. Ric Flair (Survivor Series 2005)

This Street Fight from Survivor Series was truly the perfect playground for "The Cerebral Assassin" to exact his due revenge. Triple H beat the ever loving crap out of his idol, in Detroit.

In full disclosure, both pay-per-view matches these two had were extremely entertaining and engaging. I appreciate them both for very different reasons. Which is why I selected both of them separately, for different reasons.

Ric Flair, obviously, was far from his prime by the early 2000s. The veteran of Jim Crockett Promotions and 16 (21)-Time World Champion spent his final years in the WWE. Somehow the 50+ year old Flair managed to steal the show several times over  during his final run with the WWE.

While not nearly as spry as he was in his heyday, Flair's knowledge of storytelling, ring psychology, and charisma allowed him to somehow thrive in the ring with men 20 or 30 years his junior. I seriously don't think he gets enough credit for working as often  and as hard as he did at his advanced age.

Triple H was in control for much of this match and pretty much full-on assaulted the man who had been his mentor for almost four years.

They popped the crowd at all the right moments and Flair showed the right glimmers of hope that he might win only to have them shut down by the ruthless ruler of Evolution.

It was the classic "Sensei being taken down by his greatest pupil" story.

7. Triple H vs. The Rock (Judgement Day 2000)

I made mention of these two's contest for the WWE Intercontinental Championship at the 1998 SummerSlam in the Honorable Mention section. I very nearly placed that match on the Countdown, but I decided to go with one of their matches that doesn't get mentioned as often.

In all honesty, these two worked much better matches than the 1998 Ladder match. This is definitely a more polished match with a much better story.

When you look at The Rock and Triple H, you see two men who blossomed at the same time in the WWE. They came in around the same time and they had very parallel careers during the late 1990s and early 2000s.
They worked with one another at the bottom of the card, the middle of the card, and later main evented pay-per-views together.

Really, they were both the men who battled over who should be the "second" biggest name in the WWE.

In saying that, the 1 Hour- Iron Man match might be the single most difficult match for a wrestler to pull off.

In 2000, The Rock's popularity might have reached it's apex, and Triple H had one of the greatest single years a wrestler has ever had. With "Stone Cold" Steve Austin gone, these two hungry men got to fight tooth and nail for who would stand above the rest in the WWE.

This position was very nearly given to the Iron Man match between Chris Benoit and Triple H from Monday Night Raw in 2004.

Although, this match serves as one of the most underrated matches in Triple H's catalog and serves as a shining example to how good "The Game" was back then. He was the most versatile and adaptable man on the WWE roster at the turn of the century.

Triple H would win this match and regain the WWE Championship after some unintentional help from a returning Undertaker.

6. Triple H vs. Randy Orton (No Mercy 2007)

2007 was a wonderful year for Orton's character, and one the best years he has ever had in his already decade long career.

Every once in awhile, usually when the WWE roster is thin, some stars have to pull double duty on a show or pay-per-view event. At No Mercy 2007, Triple H wrestled, not twice, but three times.

Orton, who was scheduled to wrestle WWE Champion John Cena in a Last Man Standing match, was awarded the title by Vince McMahon at the beginning of WWE No Mercy. Triple H took issue with Orton being handed a title and challenged him to a match. Triple H would defeat Orton for the WWE Championship and go on to defend the title against his schedules opponent, Umaga, later that night.

The newly christened "Viper" wasn't done. He utilized his rematch clause to make the main event of WWE No Mercy a Last Man Standing match against the WWE Champion, Triple H.

Both men were still weary from their matches earlier in the night, but that desperation they displayed with their physicality was perfect for the match type they were in.

Tooth and nail. Barely able to stand. Scratching. Clawing.

This was such a unique and interesting night for both Triple H and Randy Orton. Three titles reigns in one night? Fast title changes like this should be used very sparingly, but after a year plus of John Cena as WWE Champion this one-night storyline felt very innovative and fresh.

The final match made Randy Orton look so credible and this story arc was, for me, the one that finally solidified him as the top heel in the WWE.

5. Triple H vs. Shawn Michaels (WWE Raw, December 2003)

Few men have had more absolute classics than these two! I mean these two real-life best friends spent the better part of a decade  either teaming with one another or beating the crap out of each other.

SummerSlam 2002, Armageddon 2003, Royal Rumble 2004, and Bad Blood 2004 all featured classic contests from these two real life best friends.

When you take the emotion and grander out of that the best Triple H versus Shawn Michaels match for me took place on a forgotten edition of Monday Night Raw on one of final nights of 2003. Which just happens to be one of the worst years for the WWE's flagship show - ever.

2003 was probably one of the most flat years WWE Monday Night Raw ever had as the premiere program for the company. Triple H and Shawn Michaels ended the year with a  bit of redemption and signaled that 2004 would be a much greener pasture for the show.

The "Heart Break Kid" and "The Game" battled in Three Stages of Hell and even a Hell in the Cell match, but for my taste their one-on-one matches were just better off without the bells-and-whistles.

This was classic Shawn Michaels battling Triple H when he was his most dastardly. He was the heel who did anything to win.

Leading into WrestleMania XX, many of the matches between "HBK" and "HHH" ended without a conclusion. That was the case here as Michaels had his former D-Generation X partner pinned, but it happened that the shoulders of Michaels were down also!

Triple H retained the World Heavyweight Champions, and the two would meet again at the 2004 Royal Rumble. Still, this gem from Raw is an absolute classic television match.

4. Triple H vs. The Undertaker (WrestleMania XXVIII)

The pacing, symbolism, and brutality that was showcased inside of that cage was unlike anything you will see on WWE television today.

Neither of these two could move as quickly as they once did, but they mask that so well by building tension and selling each move like it was a knockout blow. That emphasis made every swing, kick, and hold feel so important.

That, sometimes, is the most clear difference you see with a match between two masters.

The WWE style of wrestling is much more focused on reacting to the action than it is to the action, itself.

One of the greatest philosophies in wrestling is to make all the action in the ring mean something. Doing a double moonsault or any other insane maneuver means nothing without the proper response from the other performer.

Triple H and The Undertaker understood that and lived by that in the arena.

This was as a big of a spectacle as WWE could make it. They brought out every bell and whistle they could think of. Triple H. Undertaker. Shawn Michaels. Three of the men who defined what the Hell in a Cell match was, at the biggest event of the year.

The Undertaker defeated "The Game," again,  at WrestleMania XXVIII and marked his 20th WrestleMania victory.

This ended their trio of matches at WrestleMania that spanned a decade and truly closed  the book on and "era" gone by.

3. Triple H vs. Chris Benoit vs. Shawn Michaels (WrestleMania XX)

A main event contest truly worthy of being the showcase of WrestleMania's 20th Anniversary. This is far and away one of WrestlteMania's best wrestled main event matches ever.

Triple H had some of the best matches of his career with both Shawn Michaels and Chris Benoit. As such, it only makes perfect sense that one of the best was a match featuring both of them.

We all know the story. Chris Benoit won the 2004 Royal Rumble and instead of challenging his brand's champion, on Smackdown!, he challenged the World Heavyweight Champion on Monday Night Raw.

Triple H and Shawn Michaels had been feuding off-and-on for almost two years and Michaels was hungry to finish the man he once called a friend. To them, Benoit was a nuisance and a thorn in their side as they tried to eliminate one another.

These ingredients produced what is quite simply one of WrestleMania's most physical and entertaining main events ever. The story was there, the action was there, and the moment was there.

It was everything the 20th Anniversary of WrestleMania deserved.

Triple H and Shawn Michaels both helped legitimize Benoit, who had been slowly working his way up the WWE card for almost four years.

Benoit made history, and did so by making Triple H tap out to the agonizing Crippler Cross Face.

The three men would go on to have a rematch in Canada, at Backlash, a month later which we talked about in Shawn Michaels Greatest Matches.

However, this match made Triple H's Countdown due to the enormity of him losing the title and his willingness to put over a man who had wrestled all over the world for 20 years.

Triple H, got to give Benoit his greatest moment. Even still, that's pretty special.

2. Triple H vs. Cactus Jack (Royal Rumble 2000)

Widely considered Triple H's definitive classic, this match captures the number two position which might unsettle some readers who believe this was the best match he ever had.

This match sums up everything that made Triple H the definitive "man" during his 2000-2001 run. Sure Austin was the top guy and The Rock had better promos, but it was Triple H who was wrestling the best matches on the show.

This was Mick Foley's definitive classic, and quite honestly the match that solidified Triple H as a top star for the next 15 years.

This was not quite as brutal as Foley's matches with The Undertaker, The Rock, or Randy Orton, but that is in no way a critique on how wonderful this display of ruthlessness from both men.

At one point during the match, Triple H event gets his leg impaled!

Like a true professional, "The Game" sold it and worked the injury into the story of his match. Foley was always the man to put over the younger guys during the late 1990s and early 2000s.

If you notice, Triple H didn't win his first WWE Championship from "Stone Cold" Steve Austin. He won it from Mankind. You know who else won their first WWE Championship from Mankind? The Rock.

I'm not trying to slam Austin, but more show how important Foley was to establishing two men who helped carry the roster. Foley made the future "King of Kings" look like a bonafide bad-ass in Madison Square Garden and he did it with absolute glee.

To this day, it still remains a huge turning point in the career of a man who now is instrumental in the future of WWE.

1. Triple H vs. Steve Austin (No Way Out 2001)

1. Triple H & Austin I.jpg

This match very much reminds me of the match between Shawn Michaels and Mick Foley in that it is a very unappreciated classic.

The Three Stages of Hell match.

A match so difficult to pull off that over nearly 15 years there has only been four of them in total. Triple H, was in all but one of those.

I have a feeling their will be some unrest with me not placing his match with Mick Foley in the number one position, but this match with "Stone Cold" Steve Austin has gone so overlooked over the last two decades that it seems a crime to not finally give it the due it deserves.

The first fall was a normal Singles match. The second, a Street Fight. The final, was a Steel Cage match. The first man to score two victories, would be declared the winner. So, theoretically, if either Austin or Triple H won
both of the first two encounters there would be no Steel Cage match. Unfortunately for them, there was.

I think Jim Ross's famous line, "this match is bowling shoe ugly," is probably the most appropriate call to sum up there three falls of this match.

Austin won the first fall and, naturally, Triple H won the second. The Three Stages of Hell match concluded with both men, exhausted, inside of a Steel Cage. Triple H would win after only being lucky enough to collapse onto Austin after hitting a knockout blow.

Austin, and his Stone Cold Stunner, would get the last laugh, of course.

After this absolute war both men went on to headline one of the greatest WrestleMania events ever, WrestleMania X-Seven, with The Undertaker and The Rock in co-mainevents. Afterwards, they would form the Two-Man Power Trip and would run roughshod over the WWE until Triple H torn his quadricep in the match we talked about in the Honorable Mention section.

Thus, ended probably the most fruitful period of Triple H's in-ring career.