When we do Top 5 lists, they’re usually about the 5 best or worst of something.  But a match or angle’s quality (which is of course totally subjective) doesn’t measure it’s impact or importance.  Did a match usher in a new era of success?  Did it enact some lasting change in the business?  Or cement the company’s position in some kind of way or crown a new king of the company?  Those are the kind of things that are bigger than just how many stars a match may have gotten in somebody’s rating system.

5. John Cena vs The Rock, WrestleMania XXVIII

At a time when WWE was coming off one of it’s worst ever WrestleManias, it badly needed a shot in the arm, which this match provided.  It was the match that brought me (and I believe lots of others like me) back to paying attention to wrestling and WWE.  Rock was the top dog from when I was last a full time fan while Cena was the current one and a guy we’d mostly just heard about, so the prospect of the former coming back for one more match against the current boss was enough of a hook to reel us back in.  The match was a bridge between generations of fans and got more than a few of us older ones to give it a chance again.  14 years later, here we still are.

4. Roman Reigns vs Brock Lesnar, WrestleMania XXXI

This was the match that set up the company for the last 11 years. Lesnar was a year off of breaking the Undertaker’s streak and into a run that would make him the in ring final boss of the company for almost a decade while Reigns was the embattled heir apparent to Cena trying to prove he belonged in that spot.  The match itself was one of the best main events ever, and then was punctuated with the arrival of Seth Rollins to cash in the Money in the Bank briefcase and assume his place ruling next to Roman.  One man went in already established as a King and two more would come out of ready to build their own thrones.

3. Steve Austin vs Shawn Michaels, WrestleMania XIV

The first of many rebirths of WWE happened here.  In 1997 Austin ascended to the top of the popularity totem pole in WWE with his outlaw persona that took on all comers and didn’t trust anybody.  The Stone Cold character was some light at the end of the tunnel that WWE had been stuck in for well over a year, getting their heads handed to them week after week by WCW in the Monday Night Wars.  His coronation at WrestleMania XIV wasn’t just a title victory, it was the official beginning of the Attitude Era where WWE would fully embrace a more risqué product and turn the tide against WCW while entering it’s most lucrative and popular period arguably ever.  While the stories of them being almost out of business in the mid 90s are a tad overblown they were in danger of being relegated to second place on a more permanent basis had things continued.  But Austin gave them an answer to the NWO, and this is where he began to cement his place in company and wrestling history.

2. Hulk Hogan vs Andre the Giant, WrestleMania III

The first WrestleMania was Vince’s biggest gamble, and this was the payoff.  The biggest match that Vince could have made among his roster at the time, and it drew 93,173 (yes, I know) fans and showed the country what was possible to do in professional wrestling.  It was the ultimate ‘scoreboard, MFers!’ moment for the WWF to throw in the face of the old territory bosses who thought Vince was insane for trying to create a national wrestling company and turn it into a major entertainment vehicle.  And it provided the first iconic WrestleMania moment – Hogan slamming Andre, a moment that would cement Hogan’s place in history forever.

1. Hulk Hogan and Mr T vs Roddy Piper and Paul Orndorff, WrestleMania I

To be blunt, none of us here are doing this without this match or this show.  This was Vince’s first big gambit to show that he could create a bigger and better wrestling company than all his competitors.  Leveraged to the gills to put on this event, Vince was wagering his entire project on the success of this event, and this was the match that sold it.  It was the perfect marriage of pro wrestling and popular culture that he’d been seeking. It parlayed Hogan and Mr. T’s previous work experience on Rocky III into a marquee match that captivated millions, even getting Hogan on Saturday Night Live.  Without this match, the last 40 years don’t happen.

Who missed the cut?

There are a couple that were contenders at the moment they occurred but ultimately did not have the longer term impact that these five had.  The Ultimate Challenge at WrestleMania VI was supposed to be a passing of the torch but the Ultimate Warrior’s flameout as world champion rendered that moot.  Batista defeating HHH at XXI was deflated by the Animal’s injury prone and short post-Mania career.  The first ever women’s main event at XXXV looks a lot more like a peak in hindsight and not a gateway to bigger things for women’s wrestling.  And finally WrestleMania 40 was being hailed as the beginning of a new golden age but, it only took a year for much of the bloom to fall off of that rose.

Relive The Undertaker’s greatest WWE WrestleMania Streak matches, ranked from 5 to 1, including classics against Shawn Michaels, Triple H, CM Punk, and more.

The Undertaker’s Streak wasn’t just about wins. It was about expectation. It was a match that became more important than wrestling for a world title on the grandest stage.

Every year, WrestleMania came with one constant: no matter what else was on the card, The Undertaker was going to deliver something that felt important. Sometimes it was about dominance. Sometimes it was about survival. And in the later years, it became about legacy.

Not every match was equal, but the best ones didn’t just protect the Streak. They elevated it. These are the matches that defined what the Streak meant.

5. WrestleMania 21 — Randy Orton vs. The Undertaker

This was the moment the Streak became a story.

Randy Orton didn’t just challenge The Undertaker. He targeted the Legend himself. The “Legend Killer” angle gave the match purpose, and for the first time, it felt like a loss for The Undertaker was a real possibility.

The match delivered on that premise. Orton controlled long stretches, played the role perfectly, and created believable near-falls that made the outcome feel uncertain. It wasn’t the most dramatic Streak match, but it was the one that shifted the perception. From here on out, the Streak wasn’t just a record. It was something people wanted to see broken.

4. WrestleMania 29 — CM Punk vs. The Undertaker

This match had a different kind of weight to it, all thanks to the work of CM Punk.

Coming off the real-life passing of Paul Bearer, CM Punk leaned all the way into the role of antagonist, pushing the story into uncomfortable territory. That edge gave the match a level of intensity that went beyond the usual WrestleMania build.

Inside the ring, it delivered exactly what it needed to. Punk’s pacing, combined with Undertaker’s presence, created a match that felt deliberate and physical without relying on spectacle. It wasn’t about topping previous Streak matches. It was about telling the right story at the right time, and it did that extremely well.

Honorable Mention – WrestleMania 26 — Shawn Michaels vs. The Undertaker

The rematch added stakes with Shawn Michaels’ career on the line, giving the match a different kind of emotional weight. It didn’t quite reach the same level as their first encounter, but it didn’t need to. The story was about finality, and the ending delivered exactly that.

3. WrestleMania 24 — Edge vs. The Undertaker

This is simply one of the most complete Streak matches from top to bottom, and Edge’s first WrestleMania main event.

Edge entered as World Heavyweight Champion and fully embraced the role of opportunist, constantly looking for openings and advantages against The Undertaker. The dynamic worked perfectly, creating a match where the challenger wasn’t just trying to survive. He was trying to outthink his opponent.

The pacing, the counters, and the finish all landed. Edge never felt outmatched, and Undertaker never felt vulnerable in a way that broke the aura. It was a balance that’s hard to achieve, and it made this one of the most satisfying Streak matches without needing extra stipulations.

2. WrestleMania 28 — Triple H vs. The Undertaker (Hell in a Cell)

By this point, the Streak had grown into something bigger than wins and losses.

Triple H vs. Undertaker inside Hell in a Cell, with Shawn Michaels as special referee, was built around legacy, pride, and the idea that the Streak might cost Undertaker everything. It wasn’t just about whether he would win. It was about whether he should keep going.

The match leaned into that completely. It was slower, more deliberate, and more emotional than previous entries, with every moment carrying weight. The finish didn’t just preserve the Streak. It reinforced what it represented. At this stage, the Streak wasn’t just intact. It was almost untouchable.

Honorable Mention – WrestleMania 23 — Batista vs. The Undertaker

Batista vs. Undertaker is often overlooked, but it played a key role in evolving the Streak into a main event-level attraction. The match was physical, fast-paced, and centered around the World Heavyweight Championship, helping elevate the importance of Undertaker’s WrestleMania presence moving forward.

1. WrestleMania 25 — Shawn Michaels vs. The Undertaker

This is the standard for big matches in all of professional wrestling.

Shawn Michaels vs. Undertaker at WrestleMania 25 is widely regarded as one of the greatest matches in WWE history, and for good reason. It had everything: pacing, storytelling, near-falls, and a level of crowd investment that elevated every moment.

What made it stand out wasn’t just the quality. It was the balance. Michaels felt like a legitimate threat without undermining the Streak, and Undertaker delivered a performance that matched him step for step. The result was a match that didn’t just define the Streak. It defined WrestleMania itself.

The Undertaker’s WrestleMania Streak worked because it evolved with the character, and the event itself.

It started as a statistic, became a storyline, and eventually turned into one of the defining legacies in wrestling history, and it’s biggest trophy. The best matches weren’t just about keeping it alive. They were about making it matter. And when it mattered most, it delivered.