My Favorite Wrestlemania Matches, #3 – The Undertaker vs. Shawn Michaels at Wrestlemania XXV and XXVI

From now until Wrestlemania, I will be counting down my five favorite Wrestlemania matches of all time, from how they came about to what impression they left on the show, the company, and the business. Today, I will revisit the classic rivalry between the Undertaker and Shawn Michaels that defined that latter stages of two legendary careers.


The Background

The rivalry between Michaels and the Undertaker dates back much farther than their final run together at Wrestlemania. The two wrestled in the first ever Hell in a Cell match at Badd Blood 1997. To give some context, that match was a month before the Montreal Screwjob and featured the debut of Kane. A few months later, Michaels survived a casket match with Undertaker at the Royal Rumble, but a bad fall on the casket was partially responsible for the back surgery that would put him out of action for four years.


On TV, the build for the match had to do with good and evil, light and dark. Even with those lofty associations, Michaels was the more heelish of the two since Undertaker could never get the fans to boo him at that point in his career. The storyline mattered very little in the first match, though, because the allure of the classic match was more than enough.


In year two, Michaels was a more sympathetic figure because Undertaker forced him to put his career on the line to get a rematch. His preoccupation with ending The Streak bordered on obsession. Again, the story was strong without any additional work by the wrestlers, but they created more pre-match intrigue the second time around.


The Matches

A simple glance at the wrestlers makes it clear that the natural storyline would be size and strength against speed and skill. Michaels jumped into that narrative with a stick-and-move strategy to open the initial match. As Jim Ross aptly pointed out only a few moments into the match, Undertaker was able to dictate the pace and quickly nailed Old School for the first signature move. Along the same lines, Michaels tried to take out Undertaker’s power advantage with a figure four.


Michaels continued to wear down the big man with a crossface to counter an attempted chokeslam. Undertaker escaped the move with a big side slam that yielded the first near fall, a dramatic flourish that would become a big part of both matches. Michaels recovered and climbed to the top rope to set up a crazy sequence of counters- Undertaker caught Michaels for a chokeslam; Michaels wriggled free to try Sweet Chin Music; Undertaker fell back to dodge the kick; Michaels tried to reapply the figure four; and Undertaker countered into the Hell’s Gate to nearly cause Michaels to submit.


The action moved outside the ring, where Michaels missed a moonsault to the floor. Undertaker tried to take him out with a tope to the floor, but famously crashed and burned into the cameraman. Undertaker barely beat the referee’s count back into the ring and Michaels showed his disappointment that he had not done enough to win the match. The resilient Undertaker side-stepped Sweet Chin Music and hit a chokeslam for a two count. Michaels made it back to his feet and hit Sweet Chin Music for his first near fall.

The match would have been a classic if it ended at that point, but Undertaker recovered to hit a Last Ride, again, only for two. It took a nine count for the wrestlers to regain their footing. Michaels tried to skin the cat rather than going to the floor. Undertaker caught him and hit a Tombstone. Michaels kicked out, to the disbelief of Undertaker and the fans.


Michaels countered another Tombstone into a DDT, an elbow drop, and a clean Sweet Chin Music. The fans were breathless when Undertaker managed to avoid the three count. They slugged it out in the middle of the ring until Michaels went for a moonsault. Undertaker caught him in midair and hit another Tombstone to get the incredible win.


Going into Wrestlemania XXVI, the prevailing feeling was that Michaels and Undertaker could not duplicate their success. Instead, everyone seemed satisfied to see the greats work together one more time. Michaels did his best to differentiate the start of the match with a throat slash gesture to taunt Undertaker out of the gates.


This time around, Undertaker dominated the start of the match with Snake Eyes and Old School until he tweaked his knee. Michaels took note and started to focus his attack on the knee. Through moves like an apron leg drop, Undertaker was able to find some success while he favored that leg. Michaels used a figure four to do further damage until Undertaker flipped to reverse the leverage.


With both men on the mat, Michaels kipped up and went straight into a chokeslam by Undertaker. When he tried to follow it with a Tombstone, Michaels countered into an ankle lock. The match’s no-DQ stipulation came into play when Undertaker caught Michaels outside the ring and hit a Tombstone on the floor. It took him long enough to get Michaels back in the ring that he kicked out of the pin and countered the ensuing Last Ride into a facebuster. Nonetheless, Undertaker got his knees up to block an elbow drop. He locked in Hell’s Gate, only for Michaels to counter into a jackknife to force a break.


Michaels was first to his feet to hit Sweet Chin Music and Undertaker kicked out at two. He immediately tried for another superkick, but Undertaker blocked it and hit the Last Ride for a near fall. In control at that point, Undertaker hurled Michaels to the floor. While he cleared off the announce table, Michaels got to his feet and superkicked him onto the table. He climbed to the top rope and delivered an outrageous moonsault through the announce table. In spite of all the damage to both wrestlers, Michaels got back in the ring and hit Sweet Chin Music for a third time, only for Undertaker to kick out again.


Undertaker blocked yet another superkick into a chokeslam, but could barely stand on his bad leg. He managed a Tombstone and Michaels kicked out. Undertaker yelled at Michaels to stay down while he defiantly grasped at Undertaker’s legs. He made another throat slash gesture and slapped Undertaker, which only enraged Undertaker. After another Tombstone, Undertaker got the win.


The Fallout

The obvious fallout from the final chapter in the Michaels-Undertaker rivalry was the retirement of the man with more great Wrestlemania matches than anyone. Michaels also helped Undertaker elevate his Wrestlemania streak to a level it had never seen. While he had wrestled good matches with the likes of Edge and Batista, it was Michaels who brought The Streak to mythical heights. Without these two matches, the subsequent showdowns with HHH and CM Punk would not have meant as much, and Brock Lesnar’s ultimate triumph would have had a smaller impact.


Michaels and Undertaker also set a very high bar for Wrestlemania in general. From the early days, the show was more about pageantry than the in-ring performance. Greats like Savage, Hart, and Austin made sure there were great matches. These two matches elevated the expectation level for all time. They allowed fans to expect that putting big names on the card would not be enough. Now, the wrestlers are expected to wrestle some of their best matches on the biggest show, as well.


Why It Worked

When I watched the Wrestlemania XXV match live, I did not fully appreciate it. Upon each viewing, I see more of the careful storytelling by both wrestlers that starts at the very beginning of the match. Both wrestlers challenge their resilience and toughness through their distinctive, individual skills. It was much more than a spotfest- nearly every move was an extension of the character traits we had seen develop over twenty years.


Both wrestlers also deserve a great deal of credit for differentiating the two matches. They used the no-DQ stipulation in the second match, but not in a gratuitous way. Where the first match focused on one-upping each other, the second one dealt with Undertaker’s bad leg. While Undertaker left the first match as a pure loner, Michaels clearly earned his respect the second time around.

2 thoughts on “My Favorite Wrestlemania Matches, #3 – The Undertaker vs. Shawn Michaels at Wrestlemania XXV and XXVI

    1. Andrew Berg

      No doubt it was great. If you’re picking between that, Steamboat-Savage at III, and what will be #1 on my list, I wouldn’t argue with any choice.

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