The Undertaker's greatest Wrestlemania Match?

My favorite I am sure will be a common answer, and that is Taker/HBK from Mania 25. I loved the build starting with them bumping into each other and Taker giving the line 'sometimes it's hell getting into heaven". I loved the white HBK, and him really getting into Taker's head. It was the first time since his match with Orton that I thought the streak was really in jepordy. Both of their entrances were fantasic, and the match itself I can't even do justice with with words. They threw everything at each other and both kept coming back. Not to mention Taker almost killing himself with that dive to the floor. THe HIAC match from this past year was great, but for me nothing will ever top Taker/HBK 1.
 
I believe that there is only one answer and that is Shawn Michales vs The Undertaker from Wrestlemania 25. The match was a near perfect, surely one of the best matches to ever happen at Wrestlemania along with Bret-Austin, Bret-Owen, Steamboat-Savage, Benoit-HBK-Triple H.

In addition, this match is what make The Streak so legendary. Who else could ever top that match? Probably nobody. Great storytelling, pure entertainment, decent build-up, cool entrances and great wrestling. It was the complete package. That's why I believe that was Undertaker's best Wrestlemania match.
 
vs Kane at WM14. It may be nostalgia, it may be a case of selective memory, but to this day I've never anticipated a Mania as much as I did 14 (as a Bret fan I looked at Austin as revenge by proxy for Bret lol) Everything lined up perfectly for that story and the execution was awesome. I was in grade 5 and couldn't possibly fathom how anyone could beat someone who had previously handled Vader so easily. As a side note I love that it was the beginning of the Pete Rose getting tomb stoned gimmick.
 
IMO, Randy Orton vs Undertaker at WM 21 was pretty awesome. His match with HBK at WM 25 was a once in a lifetime match and the rest were obviously pretty decent. I'm hoping that he puts on a great match with CM Punk at this years Wrestlemania, infact I hope Punk proves that he is better than Triple h and can put a better match on that HHH could on any given day.

The Undertaker vs John Cena at Wrestlemania 30 is going to be insane!
 
His match with Giant Gonzalez at Wrestlemania IX was one for the ages. How many people can claim that they got attacked by a sasquatch wielding a rag of chloroform and lived to tell the tale? The wrestling quality was out of this world, the build up was a masterpiece. This was one of the greatest matches of all time, period!


Also, his first match with HBK was somewhat decent.
 
Wrestlemania 24 Undertaker vs. Edge. It was one of the only times that i felt the streak was truly on the line ( I haven't felt it since) just with Edge being " the ultimate opportunist" and with Hawkins and Ryder to help him. There was just alot of build around the match that I personally liked
 
His match with Giant Gonzalez at Wrestlemania IX was one for the ages. How many people can claim that they got attacked by a sasquatch wielding a rag of chloroform and lived to tell the tale? The wrestling quality was out of this world, the build up was a masterpiece. This was one of the greatest matches of all time, period!

Actually, this is the 'Taker match that I remember the most from my childhood. I've always been the biggest 'Taker fan and when this match happened I thought that there was no way that 'Taker could beat him. That being said, it is far away from his greatest WM match.

Obviously 'Taker/HBK 1 at WM 25 is his best one, however, my favorite of all of 'Taker's WM matches so far was 'Taker/Flair at WM 18. The build was incredible with 'Taker attacking Flair's friends and family and the match, IMO, was the best of the night that night. Also, I was still marking out for Flair's return. I've always been a Flair mark too.
 
I only go back to Wrestlemania X8 due to my age, so I'll have to nominate his latest match against HHH.

People go on about the matches where they genuinely thought the streak would end because of the opponent, but I would wager every penny I own, that when HBK hit Sweet Chin Music and then HHH hit The Pedigree, every single fan around the world thought STREAK OVER.
 
The last one that I thought he was going to possibly lose was the FIRST one with Triple H at WrestleMania 17.

It was before the WWE went full on in acknowledging the streak and playing it up every year ... and Triple H was one of the hottest stars in wrestling. It seemed very probable that Undertaker would lose ... but he came out on top. In hindsight, it makes me realize that the WWE was already starting to think about booking future WrestleMania's around the streak.

The best actual match is hands down vs. Michaels at WM 25. Not even close really.
 
I thoroughly enjoyed his match with Michaels at WM 25. I've said it once and I'll say it again that "Mr. Wrestlemania meets the Streak" was the closest we have come to WM3's "the unstoppable force meets the immovable object". The two ring veterans showed that they were truly at the top of their game and could outdo anyone on the roster.

However with that said, from a purely bell to bell match, my favorite Taker match would be his first match with HHH. It was pure action from open to close and not just a few big spots which seems to be the case with Taker's most recent matches with HHH and HBK
 
I know the outcome was never in doubt, and it's just an endless procession of high spots, but the 2nd Triple H match actually made me question if Undertaker would lose at certain points. The same can be said with last years Hell In A Cell to a certain degree. That's why it'll always consider it his greatest match. Not my favorite, just the one I appreciate the most.

As great as the matches were with Shawn Michaels, they don't touch their '97 Cell match. That'll always be at the back of my mind when I watch them.
 
WM 25, HBK vs. Taker. Their WM 26 match was good, but I didn't like the fact that Taker was limping for 75% of it. 25 is a classic though.
 
Undertaker has had a lot of great WrestleMania matches and to only pick one that's a hard one.


But the one that comes to my mind is his match with Randy Orton at WrestleMania XXI, The build up to that match was intense

Orton Lighting the casket on fire with the Undertaker in it Undertaker in the Open Casket was just brilliant how he laid still the way he did I could never be able to do that.

And the double wide casket with bother Bob Jr and Randy and them both looking at them selves that was one of the most shocking and creepiest segments I have ever seen.



Now the match was just epic when Randy put Taker in his own move and he kicked out the look on Orton's face was priceless the '' Oh Shit now what do I do to beat him ''
 
This is a no brainer for me. The Undertaker vs Shawn Michaels at the 25th Anniversary of WrestleMania. The Undertaker is my idol and I was stoked to be there live to see him face who I would consider the greatest in ring performer of all time, HBK. The match with thrilling, there were times where I legit thought the streak may come to an end, and even feared for a moment that I drove all that way just to watch my hero die when Simm Snuka decided not to catch Taker and allowed him to take a forehead bump! But when the dust settled Taker lived, the streak lived, and I completely lost my voice screaming. Loved every minute of it.
 
I liked WrestleMania XIX. Undertaker with Nathan Jones vs. Big Show and A-Train. I thought, after Jones was attacked by the F. B. I., that this was it for the American Bad @$$. Of all his WM matches, being that this was a Handicap match with the World’s Largest Athlete and Lord Tensai, you had to believe the Streak was at risk. Plus the entrance was cool with Limp Bizkit. HAHA!!
 
Everyone here makes good points. The HBK matches were awesome. I really enjoyed the HHH matches, all three of them. But, I'm going to go another route.

Personally, given the buildup to the match, and the fact that the match itself was another part of building The Undertaker into the legend that he's become, I'm going to go with Wrestlemania VIII, against Jake Roberts. I recently watched that match, and the leadup to it, and everything clicked. It all flowed in a logical manner, which is important to the old-school wrestling fan in me.

Sadly, a lot of today's wrestling stories feel like they're forced. Case in point, exactly why was Shawn Michaels butthurt about losing to Undertaker at XXV that he was willing to both abandon his morality at Elimination Chamber AND put up his career, all in a final attempt to stroke his own ego?

Please note that I'm not talking about Shawn Michaels, the person. I'm talking about Shawn Michaels, the character. There was absolutely nothing that he could gain by doing all of that. The match at XXVI was, in my opinion, better than at XXV. But, the build-up to that match was just so forced that it took a lot of the enjoyment out of the match for me.
 
WrestleMania XXV vs Shawn Michaels.

As many others have said (myself included at one point) it was a classic. The match was a masterpiece. Everything from the entrances to the finish were pitch perfect. The crowd was electric. Even the botch was badass. Like I said before, what else really needs to be said? Almost everyone in this thread has at least given the match props, while the overwhelming majority agrees that it's clearly the best.

No matter if I spell it out in quotes, write it out in my own words, or just put up a video of the match, the bottom line is clear: Undertaker vs. HBK isn't just a great 'Taker at 'Mania match, but an all-time great match, period.
 
no contest for me vs HBK 1 and 2. with the first one just nudging out the second, but for me the second had a better leadup and grander entrances.

tho as midgensa chose his first match with Triple H at Mania 17 was a donny brook.

But it speaks volumes of HBK and Taker that they are both really over the hill in terms of how long they have been going at it and yet they both gave the fans 2 matches of a lifetime.
 
The Undertaker has produced some great matches at Wrestlemania, but if I had to pick the one that I though was the greatest then I would have to say Undertaker vs HBK at Wrestlemania 25. the build up to the match was done brilliantly and the match was first class. both men pulled out all the stops and you really had no idea who was going to win. a close second would have to be last years wrestlemania match against HHH, with third place going to Undertaker vs Jake the snake at wrestlemania 8.
 
Like most others, I have to go with his match against Shawn at Mania XXV. This match had it all, great build, story and exceeded expectations in the ring. Also unlike their 2nd match, you had no idea based on the in ring action who was going to win. Taker/Shawn II suffered from the same thing that Taker/Trips III did in that you knew about halfway threw the match it was over.

While Taker/Shawn I is my unquestioned greatest Taker Mania match, there are a few other matches that I feel are some of Taker's greatest matches that deserve recognition.

Mania XIV Taker v Kane: One of the best builds in Mania history and the match was really good too. It also helps when you really don't know who is going to win the match.

Mania XVII Taker v HHH: This was their 1st Mania match and this is during Taker's "American Bad Ass" gimmick which I really didin't care for, but this and his work with Brock are the only highlightes of this time. This was a great street fight that was just brutal.

Mania XXI Taker v Orton: This was the first and really only time during Taker's streak that he had a match with a young up and comer who you could see getting the win as a major push. Orton already had a title reign by this time so he was legit. Great build with a great match and the fued continued for most of the year.

Mania XXIV Taker v Edge: A little biased cause Edge is one of my all time faves, but this was a really good match and with Edge's success over Taker in the past there was enough doubt to make this match believable.

Mania XXVII Taker v HHH: Their second matchup and this might be Takers second best Mania match. Great street fight that exceeded thier first matchup. This late into the streak the way this match made you believe during the match that Taker would lose was enough to make it great.
 
Excellent topic! :)

None of his earlier matches really stick out to me, at least not in a positive way. The Giant Gonzalez VS Undertaker match certainly stands out, but in a bad way. That match was horrible to begin with and the controversial finish makes it the worst Undertaker Wrestlemania match. The others among his first 5 matches don't stand out much. The first really good one was Kane at Wrestlemania 14, the first time I watched it as a kid I really thought Undertaker was going to lose and it would remain one of his most difficult wins to obtain at the biggest show of the year.

A few other good ones include all three Triple H matches (17, 27, 28), Randy Orton at Wrestlemania 21 who under the Legend Killer gimmick stood a small chance of winning unlike most victims of the undefeated streak, Edge at Wrestlemania 24, and even the Batista match at Wrestlemania 23 exceeded my expectations. None of the other matches even come close to the two Shawn Michaels matches though. Wrestlemania 25 and 26 saw two legends face each other at the biggest show of the year in matches that stole the show both years in a row. I was there live in person to see the first Michaels VS Taker match at Wrestlemania 25 and I can say it was the experience of a lifetime as a fan to get to see that live.

The first Shawn Michaels match was a little better than the second one though so it gets my vote as Undertaker's (and Michaels' too honestly) best Wrestlemania match. It's regarded as one of the best matches in wrestling history for a reason. From the Heaven VS Hell themed promos/entrances to both legends going through their entire arsenal of skills in the ring, to the fact that this lasted 30 minutes but remained exciting the entire time, this match had everything a wrestling fan could ever ask for. I really cannot see why any other Undertaker match at Wrestlemania could possibly earn someone's vote other than maybe the other Michaels match at Wrestlemania 26.
 
Pretty tough call...

Jake Roberts: Roberts was a big deal, a legit star, and Taker was an up and comer. First major singles match for Taker at WM and a huge win

Sid Justice: May not have been a classic but it is one of the few times Taker got the top of the card and won a World Title

Kane: Crazy feud, highly anticiapted, good stiff match

HHH (WM 17) & Ric Flair (WM 18): After these two matches The Streak actually starts to get noticed. Both excellent matches, both impressive endings, and the build for WM 18 was exceptional, a show stealer match on a card that featured Rock-Hogan which is impressive

Batista: Batista looked like the future of teh company, and may well have been had he stayed and not left wrestling on his own. Excellent back and forth match with a good mix of technical wrestling, brawling, and the usual "Big Man" power stuff. One of Batista's best all time matches

Edge: More great build up, The Streak (Taker undefeated at WrestleMania) vs The Streak (Edge had beaten Taker every time they wrestled) with The World Title on the line. The story of the actual match where Edge seems prepared to counter all of Taker's usual offensive moves and avoid any big power moves actually sets the stage for ...

HBK: I think the second match was more important to his career but both were excellent. The first match was similair in concept to Taker-Edge in that HBK seemed prepared with a counter or excape for virtually all of Taker's usual offense but still couldnt put him away.

HHH: The build for the second match wasnt very good but they clearly stole the show on what was otherwise an very lack luster WM. Their final battle had great build, and was about as intense a match as you are likley to see, despite HBK's somehat cheezy overselling as guest ref, this is one of the rare moments in recent years where you really though The Streak might end. The final moment, where all three walk back to the locker room together, is a great moment as well, the three guys who helped carry the company through the dark days of The Monday Night Wars all the way to the Post Attitude Era. It was one of those rare moments like Sting embracing Flair at the conclusion of The Final Monday Nitro that really stood out as historically special for long time fans.
 
I have to go with Shawn Michaels vs The Undertaker from the 25th Anniversary of WrestleMania hands down. The Undertaker has had some great matches at WrestleMania, here is how I would rank them:

1.) vs Shawn Michaels (WrestleMania 25)
2.) vs Randy Orton (WrestleMania 21)
3.) vs Shawn Michaels (WrestleMania 26)
4.) vs Triple H (WrestleMania 28)
5.) vs Edge (WrestleMania 24)
6.) vs Triple H (WrestleMania 27)
7.) vs Kane (WrestleMania 14)
8.) vs Batista (WrestleMania 23)
9.) vs Kane (WrestleMania 20)
10.) vs Triple H (WrestleMania 17)
11.) vs Ric Flair (WrestleMania 18)
12.) vs Diesel (WrestleMania 12)
13.) vs Jake "the Snake" Roberts (WrestleMania 8)
14.) vs Psycho Sid (WrestleMania 13)
15.) vs Jimmy "Superfly" Snuka (WrestleMania 7)
16.) vs Mark Henry (WrestleMania 22)
17.) vs Big Bossman (WrestleMania 15)
18.) vs King Kong Bundy (WrestleMania 11)
19.) vs Big Show & A-Train (WrestleMania 19)
20.) vs Giant Gonzales (WrestleMania 9)
 

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