TJR WrestleMania’s Greatest Matches: The Undertaker vs. Shawn Michaels @ WrestleMania 25

It’s a match that a lot of fans consider to be the greatest WrestleMania match of all time and perhaps the best WWE match ever. It took place at the 25th WrestleMania in 2009 – The Undertaker vs. Shawn Michaels.

They are two men that helped make WrestleMania as special as it is in a match that should have been the main event, but it wasn’t. Let’s go back to 2009 for this one.

Who: The Undertaker vs. Shawn Michaels @ WrestleMania 25

When: April 5, 2009

Where: Reliant Stadium in Houston, Texas

The Build

When Michaels returned to WWE as a regular in the summer of 2002, he was a Raw guy from that point forward while Undertaker was a Smackdown guy. Their paths didn’t cross until the 2007 Royal Rumble when they were the last two men in the match. They had a legendary sequence to end that match with Undertaker ending up victorious. A year later in 2008, they were numbers 1 and 2 in the Rumble, so it was furthered that way as well.

The match was set up after Shawn Michaels ended his feud with JBL in early 2009. He was very happy, so he decided to challenge Undertaker at WrestleMania and try to be the first person to get a win after Undertaker was 16-0 at WrestleMania. It was the man with The Streak versus the man known as Mr. WrestleMania. Since it was the 25th WrestleMania, it was fitting that this was the matchup. They mixed religion with the match a bit as Michaels talked about having eternal life and Undertaker telling him that sometimes it was hell trying to get to heaven.

Perhaps the build could have been more, but they really didn’t need to do that much. Michaels had been in WWE since the late 1980s and The Undertaker started in 1990. They had an awesome feud in 1997 and went their separate ways after that. Setting this match up at the 25th WrestleMania was a smart move.

What I Thought Back Then

My expectations were very high. Their match at In Your House Badd Blood in October 1997 was one of my favorite matches ever. Their last singles match was at the 1998 Royal Rumble. We had to wait 11 years to see it again. I can remember re-watching the end of the 2007 Royal Rumble before I watched this match because it got me excited about what they could do in a WrestleMania match.

I didn’t think Michaels was going to be the guy to end The Streak of The Undertaker. I don’t think most people did. The feeling was always that somebody younger was going to do it rather than somebody that was of similar age to Undertaker like Michaels was. That didn’t matter, though. It’s not about wins and losses all the time. It’s about having great matches, which I expected them to do.

It’s also worth noting that both guys are the same age. Undertaker turned 44 years old a few weeks before the match and Michaels turned 44 a few months later. In pro wrestling, sometimes guys in their 40s slow down significantly to the point that you can say they lost a step. That doesn’t apply to these two legends. They were still capable of having amazing matches as they proved many times over the years.

This was the first WrestleMania match between two of the biggest legends in the history of WWE. I was pretty f’n excited.

Here’s my full review of the match, which was written in 2012.

Michaels made his entrance in a white coat, descending on a platform. When he reached the stage, his music started up. He said a prayer and walked to the ring with a purpose. The crowd gave him a big ovation. Michaels looked towards the entrance as Undertaker arrived on the scene.

He rose from under the stage. I guess he rose from hell while Michaels descended from heaven? The announcers put over the light vs. dark idea too. What’s cool is that they were both guys from Texas and this match took place in their home state, so it likely meant a lot for them to have this match in Texas. Four minutes after Taker’s music started, he entered the ring.

The Undertaker vs. Shawn Michaels @ WrestleMania 25

The story was that Michaels wasn’t intimidated by Undertaker. He was ready for him. Michaels used his speed to get some shots in early, hitting in a few hard chops to the chest. Undertaker overpowered him in the corner, Michaels faked a knee injury and then recovered quickly to attack Undertaker with punches to the head. Undertaker hit him in the head with punches of his own. Michaels was whipped into the corner, which flipped him upside down and then Undertaker gave him a back body drop. Undertaker gave him a Gorilla Press Slam followed by an elbow drop. Undertaker hit the Old School clothesline to a standing ovation. A running boot in the corner by Undertaker was avoided in the corner. Undertaker sold the right knee so Michaels focused on it with an attack to the back of the knee. Michaels put Undertaker in his inverted Figure Four Leg Lock submission. Undertaker fought out of it with punches to the head. Michaels dropkicked the knee. Undertaker was able to catch him and drove Michaels back to the corner. Running clothesline for Undertaker in the corner. Two of them. Snake Eyes into the corner turnbuckle followed by the big boot to the face and a leg drop to Michaels. That was an Undertaker sequence of moves that we would get used to over the years. Undertaker went for the Chokeslam, but Michaels countered it with a Crossface. That was an awesome counter. Undertaker countered it into a side slam for two. Crowd was popping for that. They were loud for much of the match, chanting the name of each man at various times. Michaels hit Undertaker with a flying forearm to the face. Kip up. Michaels hit two inverted atomic drops and then a clothesline. Michaels went to the top, Undertaker caught him with a Chokeslam, Michaels countered that, went for the Superkick, Undertaker dropped to his back to avoid that and Michaels went for the Figure Four. Undertaker countered that with Hell’s Gate to a huge ovation! Michaels was able to get his feet on the ropes. Ref made Undertaker break it. That was an outstanding sequence of moves right there. With Michaels body hanging off the apron, Undertaker hit a boot to the face and then his leg drop on the apron missed because Michaels was able to avoid it. Baseball slide dropkick by Michaels. Michaels went to the top rope and he jumped off the top with a moonsault. Undertaker moved out of the way. Michaels went crashing to the floor. His knee went smashing into the floor. The ref Marty Elias was checking on him. Undertaker got to his feet. He ran the ropes, he jumped over the top rope and Michaels put a camera man in front of him. JR: “Oh my God!” The camera man was Deuce from the Deuce & Domino tag team aka Sim Snuka, the son of Jimmy Snuka. He failed to get in the right spot to catch Undertaker for that spot. Soon after, he was released from his contract. It was a very scary landing for Undertaker. I remember thinking he was legit hurt because he dove all the way over the top rope and landed right on his head. What a tough man he is to be able to continue. The ref was also down because Michaels pushed him out of the way, so everybody was out on the floor. On the replay, you could see that Deuce should have been up about a foot to break Undertaker’s fall.

Back in the ring, Michaels was the first one to recover as he pulled himself into the ring. He grabbed the ref Marty Elias while another ref Chad Patton checked on Undertaker. Then Chad ran to the back. That was likely done to check on Undertaker’s health. Michaels stood the ref up in the corner, telling the ref to count Undertaker out. The crowd wasn’t a fan of the countout win, but Michaels was hoping it would be good enough. Undertaker got back to his knees and then rolled in after a count of nine to a standing ovation from the crowd. How many times do you see a standing ovation from a guy getting back into the ring to break a countout? Special match. Michaels went for the Sweet Chin Music. Undertaker caught him, gave him a Chokeslam and Michaels kicked out at two. It wasn’t just a Chokeslam, but it was one of the most impressive ones you will ever see because of how Michaels took the move. Great nearfall. Undertaker went for Tombstone, Michaels slipped out, Taker choked him, Michaels broke it and hit Sweet Chin Music out nowhere. Michaels was slow to cover, so Undertaker got his shoulder up at two with the crowd cheering loudly. Michaels kipped up again. Undertaker choked him and went for the Last Ride powerbomb. Michaels slipped out, attempting to get a sunset flip. Undertaker countered that, booted him in the gut and hit the Last Ride powerbomb for one…two…no. Another amazing nearfall. The crowd popped HUGE for that. Undertaker sold it great by selling his frustration at the move. Undertaker went to the top rope. He went for a Michaels-like Flying Elbow out of desperation. Michaels moved. Undertaker whipped him in the ropes, Michaels did his skin the cat move, Undertaker caught him off of that and gave him a Tombstone in the center of the ring. Wow, that was such a great spot to do. Undertaker folded his hands on his chest for the one…two…no. Michaels got his shoulder up. Best nearfall ever? Everybody thought that was it. The crowd was popping loud for everything in this match as they should have been. The camera shot immediately after the move was perfect because it focused on Undertaker’s “what the hell?” face because he was shocked that Michaels had kicked out. The replay showed how great Michaels was at selling that sequence because he was shaking trying to get out of the hold. Undertaker did his throat slash gesture. He tried to pick Michaels up for another Tombstone, but Michaels countered it into a DDT, which was a very unique counter. It didn’t connect perfectly. It got the job done, though. Michaels found the strength to get to his feet and he climbed to the top rope. Flying Elbow for Michaels. He pulled himself to the corner where he tuned up the band for the Sweet Chin Music. Michaels connected with Sweet Chin Music right on the jaw to a huge pop. One…two…no! JR: “Good God almighty the match continues! This classic is continuing! The world is watching a classic!” If the Tombstone spot was the best nearfall in wrestling history, that one might have been the second best. Amazing. They were on their knees, then made it to their feet as Michaels threw chops while Undertaker threw punches. The crowd responded to every blow. Then Undertaker decided that was enough, so he just booted him in the face. Michaels slipped out of a Tombstone attempt. Undertaker’s charge into the corner was countered with a Michaels boot to the face. Michaels went to the top. Moonsault is caught by Undertaker. Tombstone. One…two…three. The match ended at 30:44. The Undertaker is 17-0 at WrestleMania. JR: “Seventeen and zero!”

Winner by pinfall: The Undertaker

Analysis: ***** Wow, what a match! They followed the Austin/Rock formula for the WrestleMania match by having each guy kick out of the big spots. I never thought Michaels was going to win at any point, but those nearfalls were as believable as any Undertaker Mania match I’ve ever seen up to this point. Even when Taker went for covers and didn’t get them his facial expressions were great. I loved some of the spots in there and there’s no point in going over the big ones because everybody knows why they work. To me, the things that stand out were moments like when they were slugging it out at the end and Undertaker just booted him down forcing Shawn to collapse in a heap. That’s great. That’s how you properly do big man/little man spots. I thought Undertaker broke his neck when he jumped over the top rope and landed violently on the floor. I’m not sure what others felt when they saw it, but I thought he was done. I loved the story of the match being about Michaels heart and ability to never gave up. He took everything Undertaker had, yet he kept on fighting. He also nearly beat Undertaker multiple times and each time he didn’t he sold that frustration. That’s what I loved so much about this time. It was about the win. It was about who the better man was. After all, that’s what wrestling should be about.

Post match, both guys were lying on their back. Ross said he was honored to sit at ringside to see a match like this. The crowd was still cheering minutes after the match was over. They showed replays of all the big moments too. Michaels left. Undertaker posed in the ring as his music played. I would have loved to see them shake hands or something to allow the crowd to give them a standing ovation, but I understand why it wasn’t done.

What They Said

Shawn Michaels talked about the match to WWE magazine in 2012:

“To fully appreciate these matches, you have to understand that there was simply a moment in time when people who made the decisions in WWE thought Undertaker and I would never wrestle. He’s too big and ominous, and I’m too small and flaky. And so, for it to come down to him and me being the guys who were the cornerstone of WWE for two decades, that was pretty cool. I don’t know if I’ve ever wrestled a perfect match, but that one in Houston came pretty darn close. It worked—and I couldn’t think of a better Superstar to have done that with.”

Here are comments from Shawn Michaels talking about the match and if it’s the best ever.

Shawn Michaels:

“It was a phenomenal match from my standpoint. I don’t know if you can wrestle a perfect match but it certainly felt that way to me. On the ride home, I can remember saying, ‘Well, that might have been the one to end it on. That was pretty darn special.’ So you knew it was good when you were doing it. You knew it was special afterwards. I will let history decide where it ranks because again, all that stuff is subjective, and depending on who you ask, all those opinions differ as well. So I try not to get too caught up into it, but it was certainly special to me.”

The Undertaker didn’t do a lot of interviews prior to 2020 when The Last Ride documentary came out on WWE Network. Here’s what Undertaker said in an interview about the match:

“I’ve got a lot but I tell you what, WrestleMania 25 with Shawn. Man, that’s just one of those matches that everything went the way it was supposed to go, for the most part. It would’ve been nice to do the dive and land on somebody but, other than the lawn dart over the top rope, that was really special.”

The Undertaker had a lot of love for the match when he talked to ESPN about it in 2021:

“That’s probably, as far as I’m concerned and my body of work, that is the epitome of a great story, great characters, and then the ability to pay it off in the ring with a quality match. I think it was probably one of my finest moments technically. There was such a huge buildup to that match, and with Shawn’s storied career and my storied career, we were in the twilight of our careers. But I remember them not putting us on last, and we both kind of took that as a slap in the face. It was looking at each other and going, ‘Alright, who’s gonna follow us?’ That’s good because you always want to go out and you always want to be at the top of the page and have people try to follow you. That night, I think we delivered on every aspect of storytelling and match quality. It was just a really special night where everything clicked. It was everything good about what wrestling is.” (Thanks 411Wrestling for the transcript.)

The Undertaker also spoke about his reaction to the match and what made the match so special to him:

“I’ve always kind of a pessimist when it comes to my matches. I would never watch my matches back with anybody else. I’d have to sit by myself so I can pick them apart and say, ‘Wow, I should have done this.’ That night, other than missing the cameraman on the dive over to the top which even added to the story because it was such a nasty bump that I took, but even that ended up turning something bad into something really good. Just everything was the way it was supposed to be and there was so much ad-lib in that match, and that is something that you can do when you have guys that you trust and have that kind of ring acumen. All I had to worry about that night was being The Undertaker. I didn’t have to worry about Shawn and what Shawn was going to do because I knew he was going to be right there. So, those are those kinds of special nights that you don’t have to think for your opponent, you don’t have to come up with something because you know he’s on the same wavelength as you are. It was the perfect storm, and I couldn’t have been more happy with how that turned out.”

Jim Ross:

“I was kind of on the outs and fading away at Wrestlemania 25. Probably one of the greatest gifts I’ve ever had was to be able to call that match with Cole and Lawler. And I just thought it was a piece of art. And I’ve seen a lot of matches and I’ve seen Shawn since day-one in the Mid-South territory. I tell kids this all the time when I do my one man show; they say ‘well, if I want to watch a match and understand psychology…’ I say I can give you a lot of matches that have great psychology. Because back in the day, there were some amazing in-ring psychology. But if you want to go in modern time and I certainly consider Wrestlemania 25 a modern era match, I have never seen a more psychologically compelling match than Shawn and Taker had that night. I had goosebumps. I had tears in my eyes. I was so emotionally wrapped up in that presentation. So if I was, as the grizzled veteran, if I was emotional, I can only imagine the impact it had on younger wrestling fans. I think on our drive home we were on the money, that might have been the one to go out on.”

Here are some comments from the referee of the match, Marty Elias:

“It was amazing. For me personally, it was something that I was in awe of being in the ring with Taker and Shawn but not to the sense where I was “marking out” (and of course we are all marks, I’ll admit that) but it wasn’t a sense that I was marking out because “Oh My God” this is WrestleMania and this is Shawn vs. Taker. I was marking out because I had this opportunity to get in and do this and for me it was everything that I had worked for. The blood, sweat and tears and all the BS and the stuff like no pay days and long car rides and if I am doing the right thing for my family and relationships going bad or whatever but for me being in that match and the match turning out to what it is today, it was all worth it. All that stuff paid off and that match was voted the greatest WrestleMania match in the history of WWE. Being a part of it and being in there is an experience I’ll never forget but it is funny that when I got to the building and we got to the outside, right before Taker did the dive and Shawn did the moonsault out and I got thrown against the barricade, you felt it. You felt the momentum that this was going to be something special because the way they had that match built you could just feel it and we had the crowd from the get-go. For it to turn out the way it turned out, I still pinch myself and am blessed every day and if my life ended today I could say that I had a great match in WWE history and I’ll always be a part of WWE history and Taker’s history and Shawn’s history and nobody else can say that.”

What I Think Now

When there’s a big man vs. a smaller man in a match like this, it’s easy to root for the smaller guy, which was Michaels. He’s at a disadvantage because the other guy has more power. We all know that. It’s what we’ve learned known since we were kids. That’s why the match is so compelling. We loved both guys due to their history as legends in WWE, but I’m sure a lot of you rooted for Michaels like I did just because he came into the match as the underdog.

It was no surprise that the crowd was into the match the whole way. Watching it again today, you can really appreciate how hot they were from start to finish. As the nearfalls started piling up, they got more into it and helped make the atmosphere even more special. Good job by everybody in the crowd in Houston that night.

That Undertaker’s leap over the top rope that ended poorly still makes me cringe. We had seen him jump over the top rope like that many times in his career, but for him to land hard on his head/neck like that was scary. Sim Snuka (Deuce) was the cameraman there and he was supposed to be there to help with the fall. The Undertaker appeared to be fine, though. He got through the rest of the match without a problem, so kudos to him for being such a tough guy.

The final third of the match was so good. Listen to the crowd after Taker got back in the ring following the dive on the floor. There were so many incredible nearfalls that the crowd bought into. An Undertaker Chokeslam nearly did it, but Michaels kicked. Michaels came back with a Superkick for just two. Undertaker nailed the Last Ride Powerbomb for two and he was so frustrated that Michaels kicked out of it. Selling emotion on his face has always been a strength of The Undertaker. Undertaker came back with a Tombstone, Michaels kicked out and Undertaker had the greatest shocked look expression he’s ever done in his life. Perfect. Michaels countered another Tombstone attempt into a DDT that didn’t connect perfectly, but it got the job done. That set up the top rope elbow and Superkick from Michaels for a dramatic nearfall that drew a standing ovation when Undertaker kicked out. The finish was brilliant. Michaels went for a moonsault, Undertaker caught him in his arms, Michaels tried to break free and Undertaker hit another Tombstone to end. What a finish.

The big question following it was where does it rank among the greatest matches ever? It’s still hard for me to say. My number one was always Hart vs. Austin at WrestleMania 13. That match was 12 years before this match. I’ve since watched this match many times. I think this match is better. There are others I really like as well, which I’ve covered over my entire writing career. This one is at the very top for me as the best match ever. It was everything I like about professional wrestling. I think Jim Ross said it best as they were going through the replays: “As a wrestling fan how can you ask for anything more?”

What a perfect way to end the show, right? Nope. Instead, we had two matches left. I think if they could do it again they would have ended the show there. It was an incredible match that could not be topped. I know that on a Legends with JBL special about The Undertaker they featured Shawn Michaels saying that it motivated Undertaker knowing they weren’t on last. Also, Triple H admitted that he didn’t think he should have been last with Randy Orton that night, but that’s what happened.

Oh and here’s that shocked Undertaker face that I love so much.

If you want to read even more about this Undertaker/Michaels match, check out Alex Podgorski’s in-depth review about it also on TJRWrestling right here.

What Happened Next

They did it again one year later, which was the last match in the career of Michaels (if you ignore a return in Saudi Arabia many years later). I thought the setup for the match was brilliant with Michaels talking about how he was so close to winning and wanted one more shot at The Undertaker. The setup of that match was brilliant. That was a five-star match just like this one was. I like this one more, but if you need an hour of entertainment in your life it’s a good idea to watch them back to back.

Final Thoughts

I think it’s the best match in WWE history, not just WrestleMania history. There may be matches with better stories going into it that might make people think another match is superior, but I rank this match right at the top.

Thank you, Undertaker. Thank you, Shawn. I’ll never forget your match at WrestleMania 25. The greatest of all-time.

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That’s all for me. Check out the full list of my WWE PPV Review archive right here. Thanks for reading.

My contact info is below.

John Canton

Email mrjohncanton@gmail.com