10 Superstars With The Most WWE PPV Wins Ever

Who gets it done on the Grandest Stages Of Them All most often?

Momentum is a massive thing in WWE these days - so big, in fact, I'm shocked there isn't a Momentum Championship residing on both Raw and SmackDown Live.

Momentum is a myth, in my opinion. Yes, sports teams might win a few games and then feel unstoppable for a while. Manchester City won the Premier League by many, many miles this season and even lost a couple of games along the way. Did their season fall apart when they scored a big, fat 'L'? NOPE! Their momentum wasn't stopped as they simply dusted themselves down and pulled the metaphorical trousers down of most PL teams once more.

I bring up momentum because in WWE today, it's apparently a necessity to win a big match. If you haven't won your last five matches on weekly television, there's very little point in you turning up for a PPV match as you've got no chance, son. And it's in PPV matches where it really counts in WWE land. Most of the time, that's where the big bucks and championships are on the line - unless you're the current incumbent of the Intercontinental or United States titles, of course.

With that in mind, here are the 10 most winningest - I've been reliably informed that's an actual word in America - Superstars in WWE pay per view history!

(a '*' has been noted next to numerous members of this list as at the time of writing, their in-ring careers have not come to a conclusion. Treat it like a not out score on a cricket scoresheet)

10. Kurt Angle (43*)


First WWE PPV match: Survivor Series 1999 - won (via pinfall) vs. Shawn Stasiak

Last WWE PPV match: WWE Greatest Royal Rumble 2018 - eliminated by Elias

Best WWE PPV match: No Way Out 2006 vs. The Undertaker

World Heavyweight Champion Kurt Angle put his title on the line against The Undertaker in a match that felt like a coming of age for him inside a WWE ring. Of course, the Olympic gold medalist was already recognised as one of, if not the best wrestler in the world - but even he admitted his best performances didn't arrive until he'd left WWE for TNA.

This is a match where Angle, the Wrestling Machine of WWE, wrestled circles around The Deadman. Few times before had we seen The Phenom on the defensive so much, with Kurt bringing out so much innovative offence to better his opponent. The finish to the match was a beauty as well, with a 'Taker Hell's Gate submission hold reversed into a pinning combination for an Angle win.

9. The Big Show (52*)


First WWE PPV match: WrestleMania XV - lost (via DQ) vs. Mankind

Last WWE PPV match: SummerSlam 2017 - lost (via pinfall) vs. Big Cass

Best WWE PPV match: Vengeance 2003 vs. Kurt Angle vs. Brock Lesnar

You're probably thinking that Show played a backseat role in this match, allowing two of the best ever to go at it hammer and tong - you'd be wrong for doing so. The Giant was an absolute monster in this contest, continuing the momentum (a myth, I know) from the ring-breaking Superplex on SmackDown a couple of weeks prior.

Of course, Angle and Lesnar brought intensity and fire few others in the history of WWE could bring, but this was a match booked as if all three Superstars were playing as themselves on a video game and had an endless supply of finishers stored up. Massive move, after massive move, after massive move made this an unadulterated Slobberknocker. Despite suffering an F-5 and Powerbomb from The Beast Incarnate, and being put through the announce table by Angle, Show powered back and hit a double Chokeslam. Angle would win the match, but there are few times (Extreme Rules 2015 vs. Roman Reigns immediately springs to mind) where Big Show brought it harder than he did here.

8. Shawn Michaels (52)


First WWE PPV match: Survivor Series 1988 - Shawn, Bret Hart, Davey Boy Smith, Dynamite Kid, Jim Neidhart, Jim Powers, Marty Jannetty, Paul Roma, The Barbarian & The Warlord defeated Arn Anderson, Ax & Boris Zhukov, Conquistador Dos, Conquistador Uno, Jacques Rougeau, Nikolai Volkoff, Raymond Rougeau, Smash & Tully Blanchard

Last WWE PPV match: WrestleMania XXVI - lost (via pinfall) vs. The Undertaker

Best WWE PPV match: WrestleMania XXV vs. The Undertaker

Simply put, the best professional match of all time. Just go and watch it if you haven't already, and even if you have seen it before, you should go and watch it again. Now. You deserve it.

7. Chris Jericho (53*)


First WWE PPV match: Unforgiven 1999 - lost (via DQ) vs. X-Pac

Last WWE PPV match: Greatest Royal Rumble 2018 - eliminated by Braun Strowman

Best WWE PPV match: WrestleMania XIX vs. Shawn Michaels

In what was Michaels' first 'Mania match in five years, he was taken to a classic by Chris Jericho. The story was fantastic, with Y2J the jealous prodigy of the piece looking to take down his hero and inspiration on the Grandest Stage of them All.

Many rank WrestleMania XIX as the (second) best 'Mania of all time, with this match the best offering on the card. Since this is the best match from the (second) best 'Mania, that should be enough to convince you it's a bloody great match and the best from Chris' storied WWE PPV career.

After the final bell is where the emotions really get notched up. With the bitter taste of defeat fresh in his gums, it looks like Jericho is ready to respect his hero and inspiration once again, offering HBK a handshake and hug combination. However, it was a ruse, as the Ayatollah of Rock 'n' Rolla kicked Michaels in the crotch and left 'Mania 19 with the last laugh.

6. Edge (61)


First WWE PPV match: SummerSlam 1998 - won (with Sable) vs. Jacqueline & Marc Mero

Last WWE PPV match: WrestleMania XXVII - won (via pinfall) vs. Alberto Del Rio

Best WWE PPV match: WrestleMania XXIV vs. The Undertaker

WrestleMania XXII's efforts against Mick Foley just miss out here, as Edge and Undertaker main evented 'Mania in a match that is underrated by far too many people - we can thank Ric Flair's retirement bout against Shawn Michaels for that.

Heading into the match it appeared to be a foregone conclusion that Undertaker would be walking away with the World Heavyweight Championship. However, the longer the match went on, the more likely an Edge victory seemed. Even though he was known as the Ultimate Opportunist, Edge showed all the traits of a thinking man's wrestler by countering everything 'Taker threw at him. And I mean everything (apart from one move). With all of his regular finishing moves not working, The Deadman applied a Hell's Gate outta nowhere for the win.

We walked into this match expecting one thing and walked away from it having seen something completely different. This is a match where Edge and 'Taker told a story that suited both of their personas down to the ground, while minimal interference from the Edge Heads and the like kept proceedings pure. A special shoutout must be given to Charles Robinson, who ran roughly 8 miles down the ramp in order to replace the stricken referee for a hilariously dramatic near fall.

5. Randy Orton (66*)


First WWE PPV match: SummerSlam 2003 - World Heavyweight Championship Elimination Chamber won by Triple H

Last WWE PPV match: Backlash 2018 - lost (via pinfall) vs. Jeff Hardy

Best WWE PPV match: SummerSlam 2011 vs. Christian

It was by this point of the Randy vs. Christian feud that the pair had the finest chemistry of any adversaries in the modern era. Their matches were crisp, the action was scintillating, and this was the event where the notch was turned up a couple.

With Christian playing a more defensive, damaged limitations game, Orton was the literal Apex Predator of the piece. The story is what made this match so great - it harks back to a thought process and execution from an era that we just don't see all too often these days. With emotions boiling over, weapons entered the ring and all hell broke loose. This was how to build a rivalry, taking things up step by step, bettering the matches from before.

4. Kane (70*)


First WWE PPV match: Survivor Series 1997 - won (via pinfall) vs. Mankind

Last WWE PPV match: WrestleMania 34 Andre The Giant Memorial Battle Royal - eliminated by Baron Corbin

Best WWE PPV match: 2001 Royal Rumble

I'm sure some of you out there will have Kane's debut during the first-ever Hell in a Cell match as his best ever PPV performance - and while I wouldn't disagree, he wasn't officially in the match so it doesn't count.

What certainly does count is The Big Red Machine's outing as part of the 2001 Rumble where he eliminated no less than 11 participants, a record that stood for a lifetime. The pièce de résistance of Kane's outing was the elimination of The Honky Tonk man, who upon starting to sing was clobbered upside the head by The Brother of Destruction with his own guitar.

Many view the 2001 Rumble as the best of all time, and since Kane was the match's best performer over a stint that surpassed 53 minutes, it's got to go down as the best pay per view performance of his storied career - a career that might not be over despite his work in politics seemingly taking precedence.

3. Triple H (87*)


First WWE PPV match: SummerSlam 1995 - won (via pinfall) vs. Bob Holly

Last WWE PPV match: Greatest Royal Rumble 2018 - lost (via pinfall) vs. John Cena

Best WWE PPV match: No Way Out 2001 vs. Stone Cold Steve Austin (3 Stages Of Hell)

Street Fights against Cactus Jack and WrestleMania classics against The Undertaker come close, but nothing beats the story and match combination from No Way Out 2001.

Traces of this match can be found as early as a year-and-a-half prior, as The Game, Austin and Mankind faced off for the WWF Championship. Following the match, HHH attacked Austin with a chair and set up their bout at No Mercy. Not long after, The Texas Rattlesnake had to take time away from the ring to undergo surgery and so was hit by a car - as you do. Upon his return in late 2000, Stone Cold was trying to work out who was driving the car, and after first believing Rikishi "did it for The Rock," it was revealed Hunter had orchestrated the entire thing. Then, after costing each other in a series of matches, the stage was set for No Way Out, with a Singles Match, Street Fight and Cage Match making up the 3 Stages of Hell.

It was as hard-hitting and as brutal as you'd come to expect from these two under the circumstances, with the backstory making things all the more meaningful. This one had everything.

2. John Cena (92*)


First WWE PPV match: Vengeance 2002 - won (via pinfall) vs. Chris Jericho

Last WWE PPV match: Greatest Royal Rumble 2018 - won (via pinfall) vs. Triple H

Best WWE PPV match: Royal Rumble 2017 vs. AJ Styles

"John Cena can't wrestle."

Hold my beer, said this match.

John equalled Ric Flair's record for world title reigns in this match, just about keeping up with AJ Styles throughout. Saying 'just about' is no knock on John's abilities, by the way. This is AJ Styles we're talking about here.

This has to be the most fluid match of Cena's career, with both men countering the other's movesets with lovely transitions. While looking bloody beautiful, there were those gritty moments that looked like they belonged in a New Japan ring rather than WWE's.

Near falls was the other masterfully executed facet of this contest, with both Styles and Cena kicking out when perhaps they shouldn't have. After surviving multiple Attitude Adjustments - one off the second rope, by the way - The Phenomenal One was caught going for the jugular one too many times, with John reversing an attempted Phenomenal Forearm into an AA, holding onto the arm, rolling through, and hitting a second to secure the win. This was arguably the single best finish to a John Cena win in a match that had everything.

1. The Undertaker (101*)


First WWE PPV match: Survivor Series 1990 - The Million Dollar Team (The Honky Tonk Man, Greg Valentine, Ted DiBiase and Cain The Undertaker) defeated The Dream Team (Bret Hart, Dusty Rhodes, Koko B. Ware and Jim Neidhart)

Last WWE PPV match: The Greatest Royal Rumble 2018 - won vs. Rusev in a Casket Match

Best WWE PPV match: WrestleMania XXV vs. Shawn Michaels

It's the greatest professional wrestling match of all time. But since I've already covered it during the course of this list, 'Taker's second best match of his near-three decade career has to be the second 'Mania meeting between The Deadman and HBK a year later - the night Undertaker sent Michaels into retirement.

You would have to say that if the pair's meeting at WrestleMania XXV didn't exist, then this would be the greatest match in the history of professional wrestling - and that's just about the highest praise you can give it. There's no need to say any more.

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Ross Tweddell

Written by Ross Tweddell

Presenter over on the Cultaholic Wrestling YouTube channel. Email: [email protected]