On August 23, 1999, in the Hilton Coliseum in Ames, Iowa, Triple H defeated Mankind in the main event of Monday Night Raw to win his first ever WWE (then WWF) Championship.
As we reach the 20th anniversary of this historic event, I want to look back on some of the best title matches Triple H has competed in.
Some notes up top, before we officially dive in. I’m only including WWF/WWE Title matches since that’s the title he won 20 years ago. Triple H is a five-time World Champion, but those matches aren’t included here. I’m also only including matches where Triple H was victorious. It doesn’t make much sense to celebrate his first title win by looking at matches he lost. So, with that out of the way, let’s get into it!
5. Triple H vs John Cena – Night Of Champions 2008
These two men have competed just six times on WWE television in one-on-one matches. My favourite of those matches took place right here in the American Airlines Center at Night of Champions.
The storyline coming into the match was that Triple H was looking to avenge his WrestleMania 21 loss to Cena, as this was their first televised meeting since that match three years prior. Cena was looking to get back the title he’d never lost, after forfeiting the WWE title some eight months prior. Added to this was the fact that the Raw brand was currently without a champion thanks to the 2008 Draft. Edge retained the World Championship earlier in the night, so going into this main event, John Cena was also looking to bring a top title back to the red brand.
The match itself was excellent and told a really nice story. Triple H sold his leg from the early stages of the match, playing off his recent return from his second quad tear the prior year. The crowd was absolutely red hot for these two men and were mostly split right down the middle. The two were nearly flawless in their execution and the end result of Triple H retaining the title was a heck of a surprise at the time since it meant both top titles were on SmackDown.
It was an awesome outing for two of the very best to ever hold the WWE title and more than deserving of the Number 5 spot.
4. Triple H Vs Jeff Hardy – No Way Out 2008
In 2008, Jeff Hardy was still looking for his first WWE title win. He was looking to grab that brass ring in Portland, Oregon’s Rose Garden by attempting to dethrone Triple H, the same man Hardy defeated for his first Intercontinental Title reign seven years previous. Triple H was coming off PPV defences against The Great Khali at SummerSlam and in a Scramble Match at Unforgiven, so he was probably looking for a standout performance here at No Way Out.
This match is probably overshadowed by the World Title Ladder Match that main evented the show, which saw Chris Jericho retain against Shawn Michaels. But make no mistake about it, it is one of the best Jeff Hardy singles matches and it shows how great Triple H was in 2008. Hardy takes a sick bump on a crash and burn to the outside at one point in the match and it emphasizes Hardy’s want and desire to capture the title. The finish is one of my favourites, seeing Hardy hit the Swanton Bomb on Triple H for what would appear to be the winner before Triple H reverses the pin into a crucifix pin of his own which scores the three count. Triple H retains but it’s obvious he narrowly escaped. As far a straight-up, regular, one-on-one title matches go, I think it’s Triple H’s best.
3. Triple H vs Stone Cold Steve Austin, No Holds Barred – WWF No Mercy 1999
Shortly after winning the WWF Title for the first time, Triple H would lose it to his future father-in-law in a moment that is somewhat mind-boggling today but was part of a hot angle at the time. Vince vacated the title since he wasn’t a wrestler (although that didn’t stop him from being the ECW Champion eight years later) and put it up for grabs in a Six-Pack Challenge match with special guest referee/enforcer, Stone Cold Steve Austin. Triple H would win the match, with Austin making the three count, only to be laid out by a stunner from Austin to close that show. Austin was already the number one contender prior to that Six-Pack Challenge, so that stunner kicked off the feud heading into No Mercy ’99.
Obviously, this show is historic for the phenomenal Hardyz vs. Edge and Christian ladder match. Because of that, this fantastic main event is somewhat forgotten. The match starts out at the top of the ramp and continues as a wild ride from there. This match reminds me of something I would’ve created with my Jakks figures back in the day, and while it is a chaotic scene, it also tells a good story and never loses the viewer. Both men have the match won with no referee to make the count early on and then spill to the outside for more carnage.
This match did a lot to help Triple H become what Jim Ross would later identify as The Cerebral Assassin. It’s a fun bit of chaos that is worth going out of your way to see if you’ve never seen the match.
2. Triple H vs Cactus Jack, Street Fight – WWF Royal Rumble 2000
So many people remember what Mick Foley endured at the 1999 Royal Rumble event, but what he did here in 2000 was so much better. To be honest, the 1999 incident is so graphic that I can’t really watch the match and enjoy it. But, with this match, Mick puts in amazing work and he and The Game deliver one of the greatest matches of that era.
The angle heading into this match was a memorable one, which saw Mankind lose his job in a Pink Slip on a Pole Match (Russo was in WCW at the time, FYI) during Triple H and Stephanie’s reign of terror known as The McMahon-Helmsley Era. Mankind eventually was reinstated after The Rock somehow convinced every WWF superstar not in DX to stage a walkout and form their own wrestling organization unless certain demands were met (including Mankind’s reinstatement). In hindsight, I really would’ve enjoyed seeing what The Rock’s wrestling fed would’ve looked like.
Mankind earned a title match but said he knew he wouldn’t be able to get the job done. Fortunately, he knew someone who could. That someone was Cactus Jack. I remember Triple H selling the Cactus reveal so vividly in my mind. He freaked out so much over Mankind shedding his mask and unbuttoning his shirt and really made the transformation to Cactus Jack seem like a big deal.
The match is incredible. The use of weapons are so well thought out. There’s very little wasted motion in this match at all. If you’re one of those people who are into Dave Meltzer’s star rating system, this was the highest-rated match in Triple H’s career to this point, with Uncle Dave giving the match four and a half stars. I don’t care about stars or thumbs up or any of that stuff, but what I do care about is good wrestling and what these men delivered on this night was beyond good and beyond great.
The finish saw Cactus kick out of the pedigree even though he was supposed to stay down for the three. Mick has said he made the decision to change the finish because he wanted to be pedigreed into the thumbtacks which littered the ring. Triple H did just that and scored the win. If you are unfortunate enough to have not seen this match, stop reading this article and watch it now!
Okay, before we get to the number one spot, I’d like to list a few honourable mentions. Triple H had several solid WWE Title matches during his run in 2008, including a Cage Match win over Randy Orton at Judgment Day, a win over Edge at The Great American Bash, and a win in a rematch over Jeff Hardy at Cyber Sunday. And I’d also be remised if I didn’t mention the Iron Man match with The Rock from Judgment Day 2000. It’s a great match, but Shawn Michaels botching the DQ ending ruins it for me every time. Now, for our number one match…
1. Triple H vs Cactus Jack, Hell In A Cell – WWF No Way Out 2000
When I chose this topic to write about, the very first match that popped into my head was this Hell in a Cell epic from 2000. To me, it’s the epitome of Triple H’s attitude era and quite possibly the best match of his entire career (though his matches with Undertaker at Mania are up there too).
The stakes of this one were more than just the WWF Title. Mick Foley put his career on the line to try one last time to not only win the title but headline WrestleMania. Of course, he would main event that year’s Mania despite losing here, but for all intents and purposes, this was the end of Mick’s full-time WWE in-ring career. He would have a brief return in 2004, and a nice run with Edge in 2006, but this really was it for Mick’s career as we knew it.
My biggest roadblock when mapping this article out in my head was trying to come up with the words to describe this match. It’s nearly indescribable. Sure, I could walk you through the events and moments of the match, but this match really felt magical from start to finish and that only comes across if you’re experiencing it first hand. Uncle Dave may have given this match the same rating as the Royal Rumble match, but I think this match was better. It’s one of my all-time favourite matches that turns up the physicality to a level that I don’t think we’d ever really seen in the WWF at that point. Mick’s bump from the top of the cage is breathtaking to this day and the thought that this was how his career (kinda, sorta, in a way) came to an end was beautifully fitting. It’s not only Triple H’s best title match of all time (and that’s for ANY title he’s ever held) but it is one of the best WWE Title matches period.
So, there you have it. Triple H has competed in some amazing matches throughout his career and these five show him at his best when he was the top guy in the company. It’s hard to believe his first reign started 20 years ago, but it is easy to see how his ascension to the top changed the way the business looked forever. Congratulations to The Game on such a monumental occasion!
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