Top 25 Greatest Matches From 25 Years of The Undertaker

This year's Survivor Series marks the 25th anniversary of The Undertaker's debut in WWE. The company has been plugging this like crazy with vignettes and specials on the WWE Network, and I thought I'd celebrate the occasion by taking a look at 25 of the biggest matches in The Phenom's storied career.

Over the course of a quarter century, Mark Calaway has battled some of the biggest names in the history of the business, but who could have thought that after his debut at Survivor Series in 1990 that would be the case? There were a lot of gimmicks that came and went during that time period, and sure, he was a big guy, but the character was very over the top, and honestly, in today's WWE, it might not even get over with fans. However, he was in the right place at the right time, and the fact that he could actually wrestle, and move the way he did for a big man, certainly didn't hurt. Back then, so many big guys didn't have the agility they have today, and they would do a lot of the power moves and would eventually just be fed to Hulk Hogan.

After floundering for six years in other promotions, including his "Mean" Mark Callous run in WCW, Calaway owned his gimmick, believed in his gimmick, and worked hard in and out of the ring to become one of the true leaders of WWE. He stuck with the company when everyone else was leaving for Ted Turner's money, and over the past 25 years, he has become one of the most respected men in the business.

Putting these 25 matches together was not an easy task, as The Undertaker has been involved in so many classics, and just in case you're wondering, no, the WrestleMania match with Brock Lesnar that broke the streak is not here. But there's so many great ones that you'll find below. Let the arguments begin.

Honorable Mentions:

-2007 Royal Rumble

-vs. Kane: WrestleMania XX

-vs. Steve Austin: SummerSlam 1998

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25 vs. Hulk Hogan - Survivor Series 1991

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Okay, I had to include this match. Was it a great technical affair? Obviously not, but this match was historic, and that's why it starts the list at number 25. First of all, it was the first ever singles match in Survivor Series history. Secondly, it was the first time that The Undertaker would capture the championship, and he did it at a time where nobody really beat Hulk Hogan. Granted, he would drop the belt back to the Hulkster six days later at the This Is Texas Tuesday pay-per-view, but winning the belt one year after your debut against Hulk Hogan is a pretty big deal.

24 vs. Stone Cold vs. Bret Hart vs. Vader - Final Four 1997

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This was a different kind of match, but I've always found it fascinating. The title had been vacated when Shawn Michaels dropped it to find his smile, and these four guys put on a show at a lackluster pay-per-view in February of 1997. In what was essentially a four-man battle royal, this is one of the better Fatal 4 Way matches, mainly due to the talent involved. These are hard to pull off, but the match went nearly half an hour, and The Undertaker would be eliminated at the end by Bret Hart, who lost the title to Sid the next night, who would lose it at WrestleMania 13 to....The Undertaker.

It's also been rumored that they had to improvise the finish, as Austin was at one point scheduled to win his first title, but was sick with the flu going into the match.

23 vs. Batista: Last Man Standing Match - Backlash 2007

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Honestly, I never thought I'd ever put Batista on any top 25 list, but this is the first of two matches on this list featuring The Phenom and The Animal. Okay, the end of the match is a bit of a cop out (double countout), but the action leading up to it is very solid. Batista proved that he actually can act by selling a leg injury throughout the match, and there were plenty of intense spots with the steps, the announce tables, and a few chairs, and of course, the obligatory nine-counts, but this is a very solid match.

22 vs. CM Punk - WrestleMania XXIX

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This match has a special place in wrestling history, as it's the last win of "The Streak". The beginning of this match was a little slow, but after a while, these two really found a groove. As is typical in these later matches of Taker's career, there were a lot of false finishes between the two. This was a nice mix of submission holds and striking, and even the urn came into play before an absolutely fantastic finish full of reversals that ended with Punk finally getting pinned after a Tombstone.

21 vs. Kane -  Inferno Match - Unforgiven 1998

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Maybe it was the novelty of the match, or maybe it was the unbelievable chemistry that these two guys had over the course of their feud that started in 1997, but I love this match. The fire surrounding the ring was something that WWE hadn't done before, and these two guys were perfect for it. And let's be honest, Taker flying over the fire into Kane on the outside was great. This is a match that will likely never be done again.

20 vs. Ric Flair - WrestleMania X8

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Shocking...a match involving Ric Flair got bloody. In a WrestleMania that featured The Rock versus Hulk Hogan, this one often gets overlooked. This was during The Undertaker's biker gimmick phase and a pipe from his motorcycle came into play during this match, which is what caused all the blood. Ric Flair was absolutely destroyed in this match, but it was very cool to see two icons of the business get after it on the grandest stage. And we got an Arn Anderson run-in, which is always nice. The win also took The Undertaker to 10-0 at WrestleMania.

19 vs. Randy Orton - WrestleMania 21

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There was no stealing the show on a card that featured Kurt Angle versus Shawn Michaels, but this match was still very solid, and really proved that Randy Orton was going to be a big star in the years to come. He had been running "The Legend Killer" for a while, and the buildup to this match was great. Obviously, The Undertaker won this match (the finish is great) to move to 13-0 at WrestleMania, but it's been said that he really wanted Orton to be the one to break the streak, but Randy wouldn't do it because of the immense respect he had for The Deadman.

18 vs. Bret Hart -One Night Only 1997

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As is the case with a lot of wrestling matches, I wasn't crazy about the ending, but the 30 minutes leading up to it were very good. This pay-per-view from the UK actually wasn't even originally shown in the United States (it was released on VHS later), but featured some great matches including this rematch from a bout you'll see later in this list. There was a lot of great back and forth in this match, but yes, the disqualification ending that gave Bret Hart the win is upsetting. I know why they do this sometimes, but in a pay-per-view that didn't really matter for storyline purposes, let's get a clear winner.

17 vs. Edge - HIAC Match - SummerSlam 2008

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This was the culmination of one of the best feuds in The Undertaker's career, one that put three matches on this list, including the very next entry. This match had a ton of great spots, including Edge spearing Taker through the cage, another spear that saw Edge run across the announce tables, a few chair shots, and just overall great storytelling. In yet another match that went nearly half an hour, The Undertaker would win with a Tombstone, but that wasn't quite it. After the match, he would send Edge through the ring with a chokeslam as the ring went up in flames. Good stuff here.

16 vs. Edge - WrestleMania XXIV

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You could easily flip-flop this match with the last one, but it was the main event at WrestleMania for the title (and I was there), so that's why this gets the nod. And it really is a great match. If you can believe it, this was Taker's first main event at a WrestleMania in over a decade, and he delivered. Edge was at the peak of his career at this point, but The Undertaker was able to keep up and at times, I thought that Edge seriously might be the one to end the streak. He got a lot of offense in, but in the end, The Undertaker moved to 16-0. I won't mention the fire that happened in the stadium afterwards due to his pyro.

15 vs. Brock Lesnar - HIAC Match - No Mercy 2002

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Hey look, it's a Brock Lesnar versuss Undertaker match. I know that Vince really only wants everybody to remember the trilogy of matches over the past year and a half, but this is the best match the two ever had together. After Lesnar beat The Rock at Summerslam that year, they needed a big name to solidify "The Next Big Thing", and who better to put him over than The Undertaker.

This was exactly the match you thought it would be back when every Hell in a Cell match had tons of blood, and Taker lost a lot of it. He lost the match too, but his willingness to put Lesnar over showed that he never thought of himself as bigger than the business, which is probably the same reason Lesnar went over at WrestleMania XXX.

14 vs. Batista - WrestleMania 23

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This may be one of the most underrated matches in WrestleMania history. Again, I know it's strange to see Batista on any "best matches" list, and while it's not the best match in The Undertaker's career, it may be the best of Batista's. When two big guys match up, you often see a lot of holds to waste time and rest, but these guys just went for it right from the start. I'd have to say the most impressive spot in the match came when Batista picked up Taker on one announce table and hit a running power slam on another. This match also made a little history, as the win from The Undertaker made him the first person to win both the WWE Championship and the World Heavyweight Championship at WrestleMania.

13 vs. Kurt Angle vs. The Rock - Vengeance 2002

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The Undertaker walked into this match with the big gold belt, but would not leave with it, and I'm completely okay with that because this match was so phenomenal. Normally, I'm not the biggest fan of triple threat matches, as they can tend to go to the "this guy needs to be out of the ring for a while" well a bit too much, and I'm not saying that doesn't happen in this match, but in this one, it doesn't take away from the quality. In a match that saw everyone do everyone else's finisher (which I always find entertaining), The Rock would emerge victorious after pinning Angle, but it was awesome to see The Undertaker keep up with two of the best athletes in the company.

12 vs. Edge: TLC Match - One Night Stand 2008

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Welcome back to the third installment of The Undertaker versus Edge in this countdown. This match is insane, and Taker goes through so much. Facing a guy that's used to this type of match couldn't have been easy, but I think he held his own quite nicely. Edge took a lot of bumps in his own right, which he should have being the younger guy, but it really was great to see The Undertaker perform at such a high level in a match that he's not best suited for.

In the end, Edge won the vacant title after sending Taker off a ladder onto four tables set up on the outside of the ring, but The Deadman got a huge ovation to end the show.

11 vs. Triple H - WrestleMania XXVII

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This match was brutal, and was the second of three legendary encounters between two of the biggest stars in company history. The Undertaker had spent the previous two WrestleManias battling Shawn Michaels and those two matches were extremely difficult to top, but these two sure tried. Triple H kicked out of a chokeslam, a Last Ride, and a Tombstone, while The Undertaker withstood three Pedigrees from The Game and took a barrage of chair shots before locking in Hell's Gate to move to 19-0 at WrestleMania.

10 vs. Mankind - HIAC - King of the Ring 1998

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This is arguably the most popular match in WWE history, which is why it's included in the top 10. Technical wrestling was never going to be a feature in this one, but I don't think anybody could have expected what happened. The Undertaker won this match, but Mick Foley was the star here. He fell off of the cage, through the cage, and had a tooth come through his freaking nose. The look on The Undertaker's face when he threw Foley off of the structure is priceless, and the sight of him standing on top of the cage as they started to raise it to tend to Mick is awesome.

9 vs. Jeff Hardy - Ladder Match - Raw 2002

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This is the only match on this list from Monday Night Raw, and I firmly believe it's one of the best matches in RAW history. The Undertaker was in full heel mode for this match, and Jeff Hardy played the role of extreme underdog in this one, but gave Taker his best Monday night match ever. The crowd was insane for this one, and for a moment, you almost believed that Jeff was going to win. He came close to grabbing the title on a couple of different occasions before Taker finally ended it by chokeslamming the youngster off of the ladder and securing the title for the win. After hitting Hardy with a Last Ride after the match, Jeff would get up and tell The Deadman he was "still standing" and just when you thought he'd endure a little more punishment, the veteran patted him on the head in a show of respect. This was a very cool moment.

8 vs. Triple H - HIAC Match - WrestleMania XXVIII

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The addition of the cell along with the Shawn Michaels factor over their previous encounter puts this one ahead. The physicality of this match certainly rivals the previous match and that spot where Triple H hit the side slam on the steps is nice. Just go back and watch Taker's back hit that metal. After once again surviving the onslaught of Pedigree after Pedigree and some Sweet Chin Music from HBK, The Undertaker prevailed for his 20th win at WrestleMania.

7 vs. Bret Hart - SummerSlam 1997

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A lot of people might not put this in the top 10, but I think it's one of The Undertaker's best performances. You always had to be at the top of your game when facing The Hitman in his prime, and Taker certainly was up to the challenge. Bret was the ultra-heel at this point with the whole anti-American thing going on and run-ins from the rest of Hart's crew only added to Taker's uphill battle in this one. With HBK as the guest referee, The Hitman and The Deadman put on a show. The end came when Bret and Shawn got into it (shocking, I know) and Michaels went to hit Hart with a chair and instead hit Taker. While Hart got the win, the finish set up a match that's still to come on this list.

6 vs. Kane - WrestleMania XIV

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In the 80s, it was a lot easier to build storylines over a period of time due to the fact RAW wasn't around, and there were only a few pay-per-views each year. I think that's what made this feud so special. After Kane was introduced as The Undertaker's long-lost brother, they spent five months in a program leading to this match at WrestleMania XIV, and the match itself didn't disappoint. In my opinion, this is one of the best matches in history between two big men.

Unlike his previous WrestleMania matches with guys like King Kong Bundy or The Giant Gonzalez or even Sid, these two kept a great pace throughout with Taker getting the win after three Tombstones.

5 vs. Shawn Michaels - WrestleMania XXVI

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If you're wondering why you've only seen Shawn Michaels as a referee on this list, it's because these two put on some of the best matches in WWE history. The size difference never mattered when they The Undertaker and HBK got together and they had amazing chemistry. It was extremely hard to top the match they had the previous year, but "The Streak vs. Career" encounter was one for the ages. This was the first main event in 15 years at WrestleMania that didn't involve a title, and that didn't matter. The back and forth and all the finishers and Taker telling Michaels to "stay down" which resulted in a slap from Michaels to his long-time nemesis made for the best Tombstone finish in history. Taker jumped on this one, his third one of the match, and got the 1-2-3, and in an amazing show of class, left the ring to allow Shawn Michaels one more moment in the spotlight. Amazing.

4 vs. Triple H - WrestleMania X-Seven

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I'm betting that of the three WrestleMania matches between these two, this isn't the one you expected to see in the top five. Remember, this is the match that Vince McMahon wanted you to forget about when the other two rolled around almost a decade later, but this was the best match these two ever had together, and it was part of one of the best WrestleManias of all time.

This wasn't billed as a No Holds Barred match, but it essentially turned into that after the ref got knocked out. The two went all over the place and hit some big spots as well as some big chair shots. I particularly enjoyed the chokeslam off of the scaffolding followed by the elbow drop from Taker. Austin's heel turn in the next match would get the headlines, and the TLC match earlier in the night got the chants, so this match is often overlooked, but not here.

3 vs. Shawn Michaels - HIAC Match - Badd Blood 1997

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I've got the feeling that a lot of people would put this at the top of this list. This match was epic. There have been over 30 Hell in a Cell matches since and I still don't think any of them have been as good as the original. Maybe it was the fact that we'd never seen the structure before and didn't know what to expect, or maybe it was simply because these two guys put on an absolute clinic. As they climbed that structure in St. Louis, we had absolutely zero idea of what was going to happen and that's always refreshing.

Not only was this match entertaining and beautifully crafted, it was historic in so many ways. Of course, it was the first HIAC match, but it was also the debut of Kane, who cost Taker this match and started that great feud. It also led Michaels back into a feud with Bret Hart for the title, one that culminated at Survivor Series that year, and I think we all remember how that turned out. Of the 32 total HIAC matches, The Undertaker has been in 13 of them, and the first is still his greatest.

2 vs. Kurt Angle - No Way Out 2006

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If you were showing a new wrestler how to tell a story in the ring, you'd show them this match. Not only were there a lot of great two-counts on both sides, the close calls from submission holds were even better. I think we sometimes forget how good Kurt Angle really was in his prime, and The Undertaker was in great shape for this match and had to be to keep up with the Olympic gold medalist.

This match gets lost sometimes because it was at the pay-per-view before WrestleMania, but had it main-evented the following month, it would probably be looked at as one of the greatest 'Mania matches in history, and there were no run-ins or extra things needed for this one. I really think WWE dropped the ball on not having this as the main event on the grandest stage of them all.

1 vs. Shawn Michaels - WrestleMania XXV

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The show ended with Triple H and Randy Orton, but there is no question what the real main event of WrestleMania XXV was. Many would argue that this match between The Undertaker and Shawn Michaels is the greatest match in WWE history. The crowd was so back and forth during this match, which actually warranted the "THIS IS AWESOME" chants that get a little watered down today. This match was spectacular. I'd even venture to say that this match, while obviously technically better, is on par with the historical ramifications of Hogan-Andre at WrestleMania III.

This is the best match of the modern era, and the finish is incredible. HBK's moonsault off the top rope, only to get caught in mid-air by Taker into a Tombstone for the three-count took perfect timing, which these two had throughout this match. The pacing of this match was perfect, and although it might not have had the emotion of everyone knowing that Shawn was retiring, the match itself is superior. This is the greatest match in the 25-year career of The Undertaker.

This is my list, but what do you think is The Undertaker's greatest match?

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