Pro Wrestling Countdown: The Undertaker's Greatest Matches

'Rowdy' Ross RutherfordSenior Analyst IAugust 13, 2010

Pro Wrestling Countdown: The Undertaker's Greatest Matches

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    Welcome back everyone to the Pro Wrestling Countdown! I am one of the biggest Undertaker fans you will ever meet and this edition of the Pro Wrestling Countdown has been a long time coming.

    In the past twenty years there has never been a professional wrestler that has stood the test of time better than The Undertaker has. 

    The Undertaker’s gimmick was supposed to be just another goof ball, out of this world, gimmick that the WWE was making a lot of their performs use at the time, but he turned into one of the most legendary characters to ever be seen in wrestling.

    The Undertaker has endured through the years because of his ability to move around the ring like someone half his size and his ability to adapt with the times. He is a cornerstone of the WWE and bridges generations and will be one of the most memorable WWE performers of all time.

    The day that The Undertaker finally decides to walk away forever will truly be a turning point in the history of professional wrestling.

    While most pro wrestlers tend to stick around long after their prime The Undertaker has managed to keep himself around this long by working a limited schedule in recent years and refusing to give the fans anything less than his very best every time he walks in the ring.

    He has wrestled some of the greatest names of all time in the wrestling business and no matter what was going on in the WWE The Undertaker was always there. He is truely loyal.

    He has aged like, in the words of Jim Ross, a fine wine as his ability to have terrific matches has only increased as time has wore on.

     So today I look at ten of the greatest matches by one of my all time favorite professional wrestlers.

    Let us look at only a small portion of the legendary career of The Undertaker…

No. 10: Undertaker vs. Batista (WrestleMania 23)

1 of 10

    Let me begin this by saying that I am by no means a huge fan of Batista or his ability to wrestle, but in this case Batista seemed motivated and ended up having one of the best matches of his career.

    Back in 2007 I really put too much stock into this match. I told everyone I knew that this was The Undertaker’s greatest match ever and obviously I got caught up in the hype of it. However, even after all the hype over this match has died down I can still sit around and enjoy it.

    This was the first time The Undertaker was fighting for a world title at Wrestlemania in over ten years. The last time was with Sid Vicious at Wrestlemania 13. The funny thing about that is that his match with Sid is an example of a horrible match between two “big men” and his match with Batista is a great example of a good match contested by two “big men”.

    This match has a fair share of haters and plenty of people who dislike it, but I still think it deserves to be on this Countdown.

    The match was a brawl more or less. It sort of reminded me of Undertaker’s match with Triple H at Wrestlemania X-7. The match even showcased of couple of “holy shit” moments. For instance, we see The Undertaker fly over the top rope onto Batista and then we see “The Animal” put Taker through an announce table.

    Really this is not even close to being The Undertaker’s greatest Wrestlemania match, but it was still a fantastic match and Taker deserves a little credit for making Batista look as good as he did in this match.

    Also, The Undertaker won his first World Championship in over five years at Ford Field on this night after defeating Batista with the Tombstone piledriver.

No. 9: Undertaker vs. Kurt Angle vs. The Rock (Vengeance 2002)

2 of 10

    This match has really gone under the radar in recent years, but truth be told it is one of my favorite three way dances of all time.  In fact the only triple threat matches I like better are the Styles-Daniels-Joe match and the Benoit-HHH-HBK match.

    This match was for The Undertaker’s Undisputed WWE Championship and while there is not too much story to go along with this match I think it is just as well as it allows you to focus on the very interesting dynamic the three employ together.

    At the time The Rock had just begun his film career and was at the peak of his popularity. Kurt Angle was having some of the greatest matches with WWE’s most talented wrestlers and accomplishing more in 2 years than most WWE stars accomplish in a lifetime and finally The Undertaker was the Undisputed Champion and the most physically dominate and intimidating guy in the company.

    So we have three of the greatest performers in the WWE at the time in the main event for the Undisputed Championship and they bring it to say the least. All three men used each other’s own finishing maneuvers after their own were not enough to win the title.

    Watching the three guys go at it is very interesting as the all have very different ways of pacing a match, but somehow they all manage to stay on the same page and wrestle at the same pace.

    The match ended with The Rock pinning Kurt Angle after the Rock Bottom. The Undertaker tried to break up the count but he was just a moment too late.

    This would allow The Rock too “pass the torch” to Brock Lesnar a few months later at SummerSlam so he could go on to become one of the WWE’s biggest stars and eventually one of the biggest UFC stars….

    I’m just saying.

No. 8: Undertaker vs. Kane (WrestleMania XIV)

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    This match is something the WWE no longer does with feuds today. Kane made his debut in October of 1997, but The Undertaker and Kane never had a single match until March of 1998 at this event.

    The WWE spent 5 month building the suspense of the fans and constructing a storyline that would keep the fans interested for not just mere weeks, but the WWE put time into making the first match The Undertaker had with his brother Kane a big deal. They waited to have the match at Wrestlemania.

    The art of constructing a long and interesting storyline that builds suspense and anticipation in the fans is dying. This match was built around a intresting, surreal, if not corny, storyline that was boiling for months and months and the pay off, this match, made all that waiting worth it.

    After Kane tombstones the infamous Pete Rose and The Undertaker makes what I think is his greatest entrance ever to the ring the long anticipated match begins.

    There is so much intensity in this match. You feel every punch and it feels as if every move could shake the entire planet. This match is in my opinion the greatest “big man vs. big man” match of all time.

    It is so easy for two big guys to have slow paced boring match. Several of The Undertaker’s previous Wrestlemania matches are good, I mean bad, example of this. His matches with Giant Gonzalez, King Kong Bundy, and even Sid Vicious were all pretty terrible.

    However, Kane and The Undertaker manage to have a fantastic match full of high impact moves and brutal brawling action. They also owe a lot of credit to the fantastic build up this match got and the time they had to develop the feud.

    Kane was viewed at the time as The Undertaker’s biggest threat to date and the fact that he dominates “The Deadman” during a majority of this match really had people thinking he was the more dominate monster. 

    The two guys were doing things in this match that most 7 feet tall men couldn’t dream of doing in the ring. At one point The Undertaker is running towards Kane and he catches Taker and puts him on top of his shoulders before slamming him down onto the mat.

    Near the end of match The Undertaker had still not been able to knock down his brother and attempted a suicide dive onto Kane who was on the outside. However, Undertaker missed and went crashing through and announce table.

    The match finally ends after The Undertaker Tombstone piledrivers Kane for the third time. Out of all of The Undertaker’s Wrestlemania matches he has never taken more punishment than in this match.

    This is how all two 7 feet giants should wrestle.

No. 7: Undertaker vs. Mankind (King of the Ring 1998)

4 of 10

    This is pretty much the most well known Hell in a Cell match of all time due to the insane spots that Mick Foley takes within the opening moments of the contest.

    The Undertaker and Mankind didn't waste any time giving the fans what they wanted and started brawling on top of the cage. As the cage's roof began to cave in under the weight of the two legends The Undertaker threw Foley off the cage even though The Undertaker, as well as many others, tried to talk him out of doing the spot before the event.

    With Foley down and ring crew coming to check on him to make sure he was still alive all The Undertaker could do was stay on top of the cage and in character. Medical assistants tried to wheel Mankind to the back, but Foley got up and went back to the top of the cage.

    The fight for a moment, but then The Undertaker chock slammed Mankind through the cage! This bump was not planned and knocked Mick Foley out. These two spots have become some of the most replayed footage of WWE television of all time and helped make this the most legendary Hell in a Cell match ever.

    This was the match that solicited Mick Foley as a hardcore legend and one of the most unpredictable performers in WWE history.

    While this match is not the best Hell in a Cell match I have ever seen, but it made both of these guys legends and that makes it worth a mention on this Countdown.

    Mankind was viewed as a unpredictable lunatic after this match and The Undertaker was thought to be merciless as he continued to assault Foley even after taking those two huge bumps from atop the cage.

    Despite being in tremendous pain and having sustained several broken bones Mick Foley continued to dish out offense on The Undertaker to give the fans something special.

    In one last effort to put The Undertaker away Mankind brought out a bag of thumbtacks, but he ended up rolling in them after suffering a chock slam from The Undertaker. The match, however I think it would be more appropriate to call it a car crash, ended with The Undertaker hitting Foley with the Tombstone piledriver.

    It was safe to say that Mick Foley was made a legend forever on this night.

No. 6: Undertaker vs. Triple H (WrestleMania X-7)

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    The Undertaker and Triple H are two of the biggest names in wrestling this generation and for the first time on pay-per-view they faced off one on one and they did it on the biggest event of the year.

    While this match was not a technical marvel it still managed to be an awesome match. It was more or less a brawl and honestly I can’t see Triple H and The Undertaker having a truly epic match any other way.

    Triple H was at the top of his game in 2001 and was better than he has ever been and had claimed to have beaten everyone. Then of course The Undertaker shows up. The rivalry isn’t particularly revolutionary or even interesting, but that’s not why this match made it this far up the Countdown.

    I was watching the match and you can tell that both of them are really motivated to have an awesome match. They seem consumed by the atmosphere of Wrestlemania and it seemed to push them even further. Triple H and The Undertaker seem to understand that this was going to be one of the biggest events in wrestling history.

    The match was supposed to be a straight one on one match, but within the first ten minutes the referee is knocked out and the match turns into a street fight which elevated the intensity of this contest to a whole other level.

    After brawling through the sea of fans in Houston’s Reliant Astrodome The Undertaker put away Triple H with a Last Ride.

    "The Deadman" walked out of his hometown with a victory over one of the WWE's most talented wrestlers at the time and his 9th Wrestlemania victory.

No. 5: Undertaker vs. Brock Lesnar (No Mercy 2002)

6 of 10

    I think that this is one The Undertaker's most underrated matches ever and one of the most overlooked Hell in a Cell matches.

    The biggest story of this match revolves around Brock Lesnar targeting the (kayfabe) broken hand of The Undertaker and that is what takes the match from great to downright amazing.

    I always thought that The Undertaker and Brock Lesnar had a really nice chemistry and I really think The Undertaker helped put him over as a legitimate WWE Champion.

    Both of them really surprised me as on paper I didn't think this match looked really good. I was not anticipating this good of a Hell in a Cell match as I was not that familiar with Brock Lesnar's ring work. However, I did know that there is almost no one who can have a better Hell in a Cell match than The Undertaker, but in all honesty Lesnar hung in there with The Undertaker and managed to perform at the same level as "The Deadman" in a match that most people think he owns.

    The match came to an end when Lesnar made this incredible counter out of The Undertaker's Tombstone piledriver and somehow got him right into position for the F-5. It was just awesome.

    Lesnar went on to become what looked like the future of the WWE, but fate had other plans and now Brock Lesnar is making the UFC millions of dollars.

    At least we have the memories of what could have been.

No. 4: Undertaker vs. Kurt Angle (No Way Out 2006)

7 of 10

    In my opinion this was Kurt Angle's last "great" match during his time with the WWE. These two wrestling legends went toe to toe with one another for damn near 30 minutes…

    This match tends to get some hate from the I.W.C., but for my money this is one of The Undertaker's greatest one on one matches ever. I think it gets some hate because it moves a little slow in the first few minutes of the match before Angle and The Undertaker begin to really bring some intensity to the contest.

    Both men pick a part of the body and spend the rest of the match focusing on wearing down that part of the body. The Undertaker starts working on the shoulders of Angle, but he isn't able to keep working on the shoulders because Angle begins to work on the knees on The Undertaker and he spends the rest of the match playing catch up with Angle.

    After being slowed down by Angle's constant assault on his knees The Undertaker spends the rest of the match trying to land high impact moves to put Angle away. This tactic holds Angle off, but not for long.

    Every time The Undertaker tried to hit a big move Kurt Angle would counter out of it and bring "The Deadman" to his knees. This is an interesting match because in most of his matches The Undertaker is usually the chief aggressor so seeing him play defense during the majority of this match is a nice change of pace.

    Angle seems to have a huge sense of pride as he had a chance to win via count out, but he made the referee stop counting and allowed the match to continue.

    Despite his effort to work on the knees and ankles of The Undertaker Angle could not make him tap out. Angle countered the Tombstone piledriver and the Last Ride into the Angle Lock, but “The Phenom” refused to tap out. You can feel the intensity of both men.

    It looked as if The Undertaker would be leaving No Way Out with the World Heavyweight Championship when he locked in his triangle chock on Angle, but Angle rolled through and got a quick three count before The Undertaker even realized what had happened.

    A few months later Kurt Angle asked for his release and got it. This match was really the last contest where we got a (some what) healthy Kurt Angle at his best in the ring.

    This is a really underrated match.

No. 3: Undertaker vs. Bret Hart (SummerSlam 1997)

8 of 10

    Like several matches on this Countdown this match has some historical importance.

    While this event is mostly remembered for the match were Steve Austin broke his neck after Owen Hart botched a piledriver the main event between Hart and The Undertaker is one of Taker's most underrated matches I've ever seen as I really enjoy the way the two of them work together.

    It is really fun seeing Bret play the heel as it makes The Undertaker that much better of a babyface. Also the spot where the Hart Foundation comes out really helps sell the fact that The Undertaker is fighting an uphill battle.

    Hart spends a majority of the match working on an often distracted WWE Champion's legs. This slows The Undertaker down making it more difficult to hit a majority of his finishing maneuvers.

    The added dynamic of Shawn Michaels makes this match feel really important and watching it you just know something screwy is going to happen and you end up sitting there watching in eager anticipation for the finish.

    The end comes when Bret spits in Michaels face leading to Shawn trying to hit Hart with a steel chair and missing and hitting the champion.

    This of course gives Hart the opportunity to pin The Undertaker and win the WWE Championship.

    On this night Bret "The Hitman" Hart would win the WWE Championship for the very last time and how ironic is it that the man who helped him win it would be the same man who would take it from him. Shawn Michaels.

    The ending to this match lead to a number one contender ship match at Bad Blood between The Undertaker and Shawn Michaels in the very first ever Hell in a Cell match which Michaels would win after the debuting Kane took out The Undertaker.

    This lead to Shawn Michaels challenging the WWE Champion, Bret Hart, at Survivor Series and the rest as they say is history...

No. 2: Undertaker vs. Shawn Michaels (WrestleMania 25)

9 of 10

    I had a little trouble deciding which Wrestlemania match I wanted to pick for the #2 position in this Countdown. Both of The Undertaker's matches with Shawn Michaels at Wrestlemania are fantastic, but I only wanted to have one on this list.

    Their first match at Wrestlemania 25 is by far soupier to their rematch at Wrestlemania XXVI when you only consider the in ring action. Plus this match occurred at the 25th anniversary of Wrestlemania in both men's home state of Texas.

    However, the storyline and build up to the match at Wrestlemania XXVI was much better and there was much more emotion and I think more people cared because it was almost a sure thing that it would be Shawn's last match. Plus they got to close the show.

    However, I decided to pick their first match, as you can already tell, because this is The Undertaker's greatest matches and their match at Wrestlemania 25 was much more entertaining than their rematch.

    I'm sure there will be plenty of people who prefer their Wrestlemania XXVI match due to all the emotion and hype around it because it was Shawn's final match. However, I think their match at Wrestlemania 25 was far more entertaining.

    The Undertaker and Shawn Michaels not only met people's expectations, but they blew them out of the water. They proved that even though both of them are well over 40 that they can still have a fantastic match. I think it may be a little overrated, but all things considered this match is our generations Hogan/Andre or Rock/Austin.

    I also think I prefer this match over their Wrestlemania XXVI match because I knew Shawn was going to retire, but during their Wrestlemania 25 match there were time when I was convinced that Michaels had a shot at ending The Undertaker's undefeated streak.

    To me this is the defining match of the WWE's "PG Era". The same way that Hogan's match with Andre defined the "Golden Era". However, this is just my opinion.

    Regardless no one can argue that The Undertaker's Wrestlemania matches with Shawn will go down as some the greatest matches of this decade and maybe even all time...

    You have to see this match.

No. 1: Undertaker vs. Shawn Michaels (Bad Blood 1997)

10 of 10

    This is without a doubt The Undertaker's greatest match of all time and in my opinion it is also the most well done Hell in a Cell match since the match’s creation.

    This match stemmed from the outcome of the #3 match on this Countdown. After Michaels cost The Undertaker his WWE Championship he wanted revenge in the worst way and got Michaels in the first ever Hell in a Cell match at Bad Blood in October of 1997.

    I may get some hate for having the top two Undertaker matches both being matches he had with Shawn Michaels, but both matches made it this high on the list for very different reasons.

    Their match at Wrestlemania 25 made it to #2 because they both far exceeded everyone’s expectations and lived up to the hype of their first Wrestlemania match. They also proved that even though they were both over the age of 40 that they could still out perform guys under half their age.

    This match, on the other hand, is #1 because it shows The Undertaker doing what made him the legend that he is. This match is brutal and for a majority of the match The Undertaker is the one dishing out punishment and exacting revenge on the "Heart Break Kid".

    The match set the bar high for future Hell in a Cell matches and in my opinion this match has not been topped even though it is nearly 15 years old.

    Both men did some really revolutionary stuff in this match. Using the cage as a weapon and climbing on top of the cage was very taboo in the wrestling world as no one had ever seen a cage like this before.

    The Undertaker and Shawn Michaels match here was a really an important part of wrestling history also.

    During the match when it looked like The Undertaker was ready to put Michaels away the lights went out and Kane walked to the ring for the first time and laid out his older brother. This set the stage for their match at Wrestlemania XIV.

    Less than a month after this match Shawn Michaels faced Bret “The Hitman” Hart at Survivor Series in a match that would go down in wrestling history forever, but for all the wrong reasons. Karma would catch up with HBK as a few months after that Shawn suffered an injury, ironically in a match with The Undertaker, which (temporarily) ended his career, but also changed his life for the better.

    Years later both men are now considered the most talented performers and biggest legends to ever step into a WWE ring. Their careers have been so similar and both men have given so much to the fans and this match will be remembered forever.

    The Undertaker is without a doubt a living legend....

    Thank you all for reading the latest edition of the Pro Wrestling Countdown.