The Undertaker character has been around for nearly 27 years, and while he’s most famous for his two-decades-plus winning streak at WrestleMania, he has a chance to set a different sort of winning record next week, when he takes on Roman Reigns at WrestleMania 33.
According to Wrestling Data (which is a really fun resource if you’re interested in stats, and I encourage you to mess around with their toggles and whatnot for a while), Undertaker has won 99 pay-per-view events (either as a singles competitor or part of a team), and no one has ever won 100 PPV events. He’s already the winningest PPV wrestler of all time, with a 99-66-5 record, but everyone likes nice round numbers, and “100” sure has a great ring to it.
If he manages to defeat Reigns for the rights to full possession of the yard, he will be the only person to make it to 100 since pay-per-views have been around.
The only other active wrestler on the WWE roster who is within spitting distance of that 100 PPV wins mark is John Cena, with 82. While Cena still has his 17th world title to win, him picking up another 12 PPV wins before he calls it quits might not be as much of a given as you might think. Since the beginning of 2016, Cena has only won two (2) pay-per-view matches, while only appearing on a half-dozen or so PPV cards.
Triple H stands at also in second with 86 wins, but is on the Undertaker schedule of a match per year, more or less, so he would need to wrestle and win a match per year for the next 14 years, which … isn’t out of the question, but still a pretty long shot. Then Kane with 70, and he’s about to enter the world of politics and will be 50 years old this year. Randy Orton’s 62 wins in fifth place give him an outside chance, but he would really need to pick up the pace.
While there’s no combined WCW and WWE lists, the winningest WCW wrestler of all time was Sting, with 57 PPV victories, followed by Scott Steiner and Booker T, both with 37 wins. I uh … I don’t think any of them are really going to challenge Undertaker on this list.
Regardless, if Undertaker does set that mark, it will likely stand for a very, very long time. Heck, 99 PPV wins will stand for a long time. The Undertaker remains the Barry Bonds of pro wrestling.