10 Times Triple H Won WWE Matches He Should Have Lost

Nobody played The Game as well as Triple H, but this list only goes to 10. Who did we miss?!

Triple H
WWE.com

Booker T.

The answer is Booker T. At WrestleMania XIX. You know the one.

No, the title of the article didn't pose the question in the first place, but the answer's still Booker T.

It gets spoken about a lot, if only because it's perhaps the best shorthand example of a tenure that chased away legions of fans that had dared to stick around after the turn-of-the-century boom. It didn't seem possible that, by 2003, WWE could do the things they chose to do in the run-up to and execution of a major WrestleMania match, and yet they did. All of them.

That World Heavyweight Championship feud was amongst the ugliest in company history, but could have reclaimed a minuscule shred of kudos had Triple H laid down on 'The Grandest Stage'. "Racist dude is racist then is validated for his racist opinions in predetermined contest" was a ridiculous Reign Of Terror pitch too far during the worst excesses of his most insecure years, but it happened and must never be forgotten.

There, Triple H won a match he absolutely should have lost. And he did a lot of that...

10. Vs Sting (WrestleMania 31)

Triple H
WWE.com

Legendary brother brother bullsh*t this, if it wasn't such a self-own.

For those that still watched WWE week-to-week during the build up to WrestleMania 31's Sting/Triple H showdown, this made absolutely no sense whatsoever. Not that 'The Game' would have cared once the whole thing was over. He got his win and his pay-per-view time after all.

How did any of this bullsh*t make air?

For months, Hunter was a vindictive villain in need of a beating. Until showtime, when he became virtuous bastion of WWE fighting one last Monday Night War against the only WCW holdout. An absurd sales pitch on television, it was one that wasn't picked up on by the live crowd until run-ins from D-Generation X and the New World Order highlighted what this thing actually was (a nostalgic p*ss about) rather than what it wasn't (the expected payoff to a serious feud with actual ramifications).

It was Triple H's night in every sense - the match went 18:36, (not including outlandish entrances and exits), then he was back out there for a lengthy angle with The Rock and Ronda Rousey.

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Michael is a writer, editor, podcaster and presenter for WhatCulture Wrestling, and has been with the organisation nearly 8 years. He primarily produces written, audio and video content on WWE and AEW, but also provides knowledge and insights on all aspects of the wrestling industry thanks to a passion for it dating back over 35 years. As one third of "The Dadley Boyz" Michael has contributed to the huge rise in popularity of the WhatCulture Wrestling Podcast and its accompanying YouTube channel, earning it top spot in the UK's wrestling podcast charts with well over 62,000,000 total downloads. He has been featured as a wrestling analyst for the Tampa Bay Times, GRAPPL, GCP, Poisonrana and Sports Guys Talking Wrestling, and has covered milestone events in New York, Dallas, Las Vegas, Philadelphia, London and Cardiff. Michael's background in media stretches beyond wrestling coverage, with a degree in Journalism from the University Of Sunderland (2:1) and a series of published articles in sports, music and culture magazines The Crack, A Love Supreme and Pilot. When not offering his voice up for daily wrestling podcasts, he can be found losing it singing far too loud watching his favourite bands play live. Follow him on X/Twitter - @MichaelHamflett