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

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

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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We Need To Talk About Kevin (Nash). Michael can be found in articles or on podcasts extolling the virtues of New Generation WWF, new AEW storylines or the new WWE push they definitely definitely won’t ruin this time.