Looking at the Best WrestleMania Matches of CM Punk’s WWE Career

Thanks to the events of the March 25 episode of Monday Night Raw, CM Punk is officially part of WrestleMania 40 – albeit in a commentary role rather than competing in the ring.

It should go without saying, but the WWE Universe is suitably excited. He’ll be ringside for the World Heavyweight Championship match between the defending champion, Seth Rollins, and the challenger, Drew McIntyre. CM Punk’s close proximity to the match means there’s a high likelihood he’ll impact who walks out of Philadelphia as the World Heavyweight Champion at the end of the night! 

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In celebration of CM Punk – still nursing a triceps injury suffered at the 2024 Royal Rumble – joining the WrestleMania festivities, we’re looking back at the five WrestleMania matches that have defined his career.

Yes, CM Punk is technically one of The Undertaker’s countless victims en route to the Dead Man’s 21-match WrestleMania winning streak. But we’d be remiss if we didn’t believe that CM Punk came closer than any other WWE Superstar to ending that streak long before Brock Lesnar did!

The buildup to the match is the stuff legends are made of – CM Punk dug deep into his bag of dirty tricks, even going as far as desecrating the memory of The Undertaker’s longtime manager, Paul Bearer. It was borderline evil – but CM Punk’s alignment with pre-Wiseman Paul Heyman led Punk down a far darker road than the WWE Universe could ever imagine.

The match itself? An instant classic. Every near fall and every submission had the fans in New Jersey’s MetLife Stadium on the edge of their seats. On more than one occasion, it looked like The Undertaker’s vaunted WrestleMania undefeated streak would come to a crashing end, but each time, The Undertaker proved the doubters wrong. Although he wouldn’t hand The Undertaker his first WrestleMania loss, CM Punk cemented his incredible legacy by turning in one of the best performances in any WrestleMania match ever. 

Not all great matches are 20-minute-plus bangers – some of the greatest matches are blink-and-you-miss–performances tucked into sub-ten-minute packages. That’s exactly what the CM Punk/Rey Mysterio match at WrestleMania 26 was.

Firmly entrenched in full-on villain mode, CM Punk spent the weeks leading up to their WrestleMania 26 encounter doing what many Superstars have done before and since – by making his rivalry with Rey Mysterio a family affair. Punk made his feud with Rey Mysterio personal, which led to one of the most frenzied matches in WrestleMania history. Of course, in the end, CM Punk got his comeuppance courtesy of a well-placed 619 by Mysterio that marked the end of the bout, but that doesn’t lessen the gravity of such an entertaining contest.

Even in a loss, CM Punk proved that he always delivers, whether he’s in the main event or an opening match.  

We still can’t believe CM Punk ran it back in 2009.

Winning WrestleMania’s Money in the Bank match once is impressive enough, but twice? In a row? That’s unheard of. Nevertheless, CM Punk won the iconic ladder match at WrestleMania 25, again claiming the Money in the Bank briefcase and preparing himself for another successful cash-in.

Like the 2008 edition (which we’ll discuss later), CM Punk’s opponents were more than formidable: Mark Henry, Christian, Kane, MVP, and other elite WWE Superstars all fought valiantly, but CM Punk used a clever combination of high-impact moves and general ring savviness to win the briefcase again. While this particular match is arguably devoid of the wild highlights that marked other Money in the Bank affairs, Punk’s ability to win against all odds – for the second year in a row – is more impressive than any moonsault off a ladder through a table.  

If you’re anything like us, you completely forgot this match even happened. It’s lost in the endless legacies of both Superstars, overshadowed by the accomplishments of CM Punk and Randy Orton over the decades.

But that doesn’t mean it wasn’t an unbelievably dramatic match.

Although he didn’t win, this match marks an important point of Punk’s career: his association with the New Nexus, a faction originally devised to cause mass destruction throughout the WWE locker room. In the eyes of the WWE Universe, it was only a matter of time before these larger-than-life Superstars crossed paths on the Grandest Stage of Them All, but unfortunately, CM Punk and the New Nexus were no match for the Viper this evening. A dramatic back-and-forth bout ended when a springboard clothesline attempt was met with a well-timed RKO. (We’re happy to report that WWE Superstars still haven’t learned not to leap into Orton’s iconic finishing move, even in 2024!)

CM Punk’s inaugural Money in the Bank victory will forever live on in the memories of fans worldwide – and for good reason.

Although the WWE Universe had been firmly behind CM Punk since his arrival in ECW years earlier, most fans were worried that CM Punk—an independent star with a “look” that many assumed wouldn’t work in modern-day WWE—would be unable to break through the metaphorical glass ceiling. His opponents in this ladder match made it all the more insurmountable: Superstars like Chris Jericho, Ken Kennedy, Carlito, and MVP made CM Punk an underdog. 

Oh, and it didn’t help that CM Punk was already unsuccessful in his first Money in the Bank match, which took place a year earlier at WrestleMania 23.

Ultimately, CM Punk wouldn’t let anyone stand in the way of his destiny –by the end of this hard-hitting, jaw-dropping ladder match, the Straight Edge Superstar stood tall with the Money in the Bank briefcase in hand. It was a match that officially jump-started his career in WWE’s main event – a position CM Punk still holds in 2024. 

You can tune in to Peacock to watch WrestleMania on April 6 and 7. In the meantime, catch up on all things WWE Universe on Peacock.