The Undertaker's streak of 21 consecutive WrestleMania victories is among the greatest stretch runs in the history of sports entertainment. For nearly a full quarter-century,The Undertaker defied the odds and kept conquering opponents (some bigger, some faster, some smarter on the Grandest Stage of Them All.
The streak began at WrestleMania VII in 1991, where he defeated Jimmy Snuka.It wouln't end until WrestleMania XXX, when Brock Lesnar took down The Deadman to stop the streak at 21-0. He now stand at 34-2 at WrestleMania, having defeated John Cena at last year's event. Even if the streak is no more, fans will continue to reflect on its history for many more years to come, like we are here. Let's take a look at the five best and the five worst matches of Undertaker's streak.
10 Best: Vs. Randy Orton (WrestleMania 21)
Randy Orton was a 24-year-old phenom during his feud with The Undertaker. He had recently completed a reign as the youngest World Champion in WWE history, and Orton was quick to point out his status as "The Legend Killer." So he turns his attention towards The Undertaker, looking to hand The Deadman his first loss at WrestleMania.
The two superstars delivered an excellent match full of "wow" moments, and their in-ring chemistry was nothing short of superb. When all was said and done, Undertaker held off Orton after hitting him with the Tombstone Piledriver to score the pinfall victory.
Bonus points awarded for an amazing buildup towards this showdown.
9 Worst: Vs. Jimmy Snuka (WrestleMania VII)
This marked The Undertaker's first WrestleMania match, and the very beginning of his streak. But we can't really sit here and tell you that his first win on the Grandest Stage of Them All was something of legendary proportions.
This was a quick and extremely rushed match, like many others on the WrestleMania VII card (there were 15 matches). As such, Undertaker and Jimmy Snuka didn't get a chance to steal the show. The Phenom emerged victorious after defeating Snuka in just four minutes and 20 seconds.
8 Best: Vs. Triple H (WrestleMania XXVIII)
One year after Undertaker narrowly defeated Triple H at WrestleMania XXVII, they agreed for a second go-around at WrestleMania XXVIII in Miami. This time, Shawn Michaels would serve as the special guest referee in a Hell in a Cell match.
The Game and The Deadman traded blow for blow in what turned out to be an extremely entertaining and jaw-dropping match. On one occasion, Undertaker kicked out despite being hit with the Pedigree by Triple H immediately after receiving Sweet Chin Music from Michaels. Undertaker finally managed to put away Triple H after hitting him with the Tombstone Piledriver, en route to a pinfall victory. Undertaker now stood at 20-0 at WrestleMania.
7 Worst: Vs. Sycho Sid (WrestleMania 13)
Sycho Sid returned to the WWE in 1995 after a brief run with WCW, and he was thrown into a feud with The Undertaker, thus entering the main event spotlight. The two superstars headlined WrestleMania 13 - a no disqualification match where Sycho Sid defended his World Heavyweight Championship.
But unfortunately for fans, this was far from a memorable main event match. The overall pace just wasn't there, and the two wrestlers didn't have much in-ring chemistry to work off of here. The match dragged on for far too long (21:19), and it finally ended with Undertaker winning by pinfall.
6 Best: Vs. Edge (WrestleMania XXIV)
This match simply had it all. It was the prime example of what a main event match at WrestleMania should look like. The entire buildup between The Rated-R Superstar and The Deadman was top-notch stuff. And when it came to the big showdown in Orlando, Edge and Undertaker simply saved the best for last. Being two of the elite in-ring performers, both Edge and Undertaker stole the show with excellent technicality and execution in this match.
At one point, it looked like Edge was about to come away with a victory after he hit Undertaker with the Spear. But the latter kicked out, and he put a dramatic end to this clinical match by forcing Edge to submit to the Hell's Gate finisher.
5 Worst: Vs. Big Show & A-Train (WrestleMania XIX)
Nathan Jones was initially going to team up with Undertaker to face A-Train and Big Show at WrestleMania XIX, but it was changed to a handicap bout. And unfortunately, this match really left a lot to be desired for fans.
This match just wasn't able to leave much excitement in any way, and Undertaker was able to come away with victory thanks to help from Jones (put a minor asterisk beside this win). The card was also stacked with better matches, including Brock Lesnar vs. Kurt Angle and The Rock vs. Steve Austin
4 Best: Vs. Shawn Michaels WrestleMania XXVI
A year after their epic showdown at WrestleMania XV, Undertaker agreed to face The Heartbreak Kid one last time, with the stipulation being that Michaels would have to retire if he lost.
Fans in Phoenix received the experience of a lifetime as Michaels and Undertaker executed numerous finishing moves on one another. There were a handful of instances where you thought the match was over, only for Michaels or Undertaker to kick out.
At his mercy, Michaels managed to to send one last message by getting on his feet, where he slapped Undertaker across the face. Finally, Undertaker executed another Tombstone Piledriver to pin Michaels, moving to 18-0 while ending the legendary and illustrious career of The Showstopper.
3 Worst: Vs. Big Boss Man (WrestleMania XV)
Even the Hell in a Cell stipulation wasn't able to rescue the lackluster match here. Overall, the actual pace and technically was far from ideal. Not only that, but the ending was extremely gruesome and disturbing; one that would never fly in the WWE Today. After Undertaker defeated Big Boss Man, he managed to tie a knot around his opponent's neck. The Phenom then raised Big Boss Man to the top of the cell.
Did I mention the match itself wasn't really anything spectacular? At least Steve Austin and The Rock took over the show in the main event.
2 Best: Vs. Shawn Michaels (WrestleMania XXV)
Not only was this the best ever WrestleMania performance by both Shawn Michaels and The Undertaker, but many consider it to be the greatest WrestleMania match of all-time. Quite frankly, it had everything fans look for in a WretleMania showdown.
If you thought their aforementioned WrestleMania XXVI was practically flawless? Well, you only had great things to say about this showdown. For the first time in years, it felt like The Undertaker actually stood a realistic chance of losing a WrestleMania match.
They laid everything out for 30:44, and The Undertaker finally conquered his greatest WrestleMania challenger yet by performing the Piledriver while Michaels tried to perform a Moonsault. With that, Undertaker was now 17-0.
1 Worst: Vs. Giant Gonzalez WrestleMania (IX)
If anybody wanted to put an asterisk on The Undertaker's perfect WrestleMania streak, this was the time to do it. The Undertaker went up against Giant Gonzalez (billed at eight feet in height) at WrestleMania IX in Caesars Palace. The match was extremely slow in pace, with no true "wow" moments - and Undertaker only picked up the victory via disqualification after Gonzalez knocked him out using Chloroform.
The match only lasted 7:33, and it marked Undertaker's only non-clean WrestleMania victory. As such, this was unquestionably the worst match in his storied WrestleMania career.