WrestleMania Week – Top 10 Streak Matches to Never Happen!

Posted on: April 3rd, 2014 by Big Cal

A couple of weeks ago, on a forum I frequent, someone posted this:


And it got me thinking… just who WOULD I pick to face Undertaker at WM to almost guarantee we got the absolute best Streak match ever? So I decided to steal his idea and turn it into a written feature for WrestleMania Week! 😛

Before I get into my top 10, I’d like to run down a list of names who either didn’t quite make the cut, or who I think other people might say or assume I might say (depending on how well you know me haha), and why I decided to keep them out of my top 10.


William Regal – I love Regal. Huge fan of him and his style, and he’s been involved in some of my all time favourite matches over the years. That being said, I just don’t think a Regal from any time period of his career Vs Undertaker from any time period would have resulted in such a great match. Their styles are vastly different, and given the size difference I’m not so sure Regal’s offence would have suited an opponent like Undertaker. I’d have definitely paid to see a big PPV match between the two just because of how much I enjoy both men’s work, but a Streak match? Unfortunately no.


Finlay – Right up there with Regal as someone I absolutely adore. Guy rocks the planet with his awesome wrestling style, and has had some killer matches in his career. While these two WOULD be more suited as opponents (proven on SD in 2007 when they had a GREAT match), I still don’t think they could have had a match worthy of what the Streak has become these days. IF it were to have happened though, I would have gone with 2006 Finlay against a BIG EVIL version of Undertaker, maybe from 2003 (Finlay Vs Undertaker at WM 19? God how awesome would that have been?!?!). But as the Streak has become something perhaps even bigger than the WWE WHC, I’d have a hard time imagining Finlay being perceived as being on THAT level against Undertaker at WM. Which is sad because given the chance Finlay could make it work.


Ric Flair – Yes, I know they actually HAD a WM match back in 2002, and it was damn good, but mid-80’s Flair was a name I first thought of when asked the question so I thought I should address it. Flair in the 1980’s was off the charts. His 1985 and 1989 years are talked about as all time great years for ANY wrestler, with both years given us some of the greatest Ric Flair matches ever. BUT kind of like Regal, I’m not sure THIS Flair, as great as he was, would have been a good opponent for Undertaker in a Streak match. Back then Flair certainly had his own kind of match that he liked to work, and I just don’t see it being a STREAK worthy match or connecting that well with Undertaker as his opponent in general. Even a babyface Flair from this time period Vs Undertaker just doesn’t feel right to me. Thankfully we did get their match in 2002 and I wouldn’t change the components in the slightest. We had a Big Evil heel Undertaker Vs an ageing Ric Flair and everything just clicked. Perfect.


Randy Savage – So this was the pic from the guy who brought up the question to begin with. Honestly I don’t see it myself. Like Flair, I don’t see them working together that well. Which is crazy when you consider that Savage had an absolutely incredible match at WrestleMania with THE ULTIMATE WARRIOR. A match like that might have had the best chance to work if these two ever had a Streak match, but honestly I’m just having a hard time imagining them really having magic together. Not doing the best job of explaining myself here I know, having a hard time really putting my feelings into words haha. Not even a Big Evil heel Undertaker Vs an ageing Randy Savage would have been good like the Flair match imo. Savage as he got older really did “lose” it as far as I’m concerned, which was a shame. I’ll just leave it at that unless I evenutally figure out a way to write down EXACTLY what I mean lol.


Christian – This is definitely more of an “honourable mention” rather than a “someone I might have picked but didn’t because…”. Take 2009 Christian, who was almost unarguably the BEST WWE wrestler at the time (and probably the entire world. Nobody in TNA or ROH came close from what I saw. No idea about Japan though), and an absolute SUPERB babyface wrestler, and stick him in the ring at WrestleMania against a 2002 Big Evil Undertaker (heel obviously) and man oh man this could have been MAGIC. Have Undertaker beat down and bloody the underdog babyface, give Christian some hope spots only for Undertaker to knock him right back down again (maybe even CHEATING to do it, which for a big guy like Undertaker would be completely unnecessary and such a HEEL thing to do), then go into a big hot finishing stretch. That’s a very basic way to state the match structure, but when you have someone like Christian who (especially in 2009 on ECW) could play such an incredible babyface working such a structured match (which has worked since like the beginning of the universe lol) against a pro like Undertaker, you would get something so far beyond basic it’s unreal. People talk about dream matches, and they are usually 2 “megastars” battling in their primes at a big event, but for me, dream matches are something more like this. Christian unfortunately isn’t a “megastar” which is why this match would never happen at WM (or anywhere now), but the match they COULD have given the time and opportunity is what makes it a dream match for me.


Ricky Steamboat – Steamboat is an all time favourite of mine, and has been involved in some of my all time favourite matches. The Flair series is what comes to mind for most people when they think of Steamboat, but you absolutely cannot forget his incredible matches against so many other opponents, 2 of my favs being Regal and Vader. The Vader match saw the Mastodon absolutely MAUL poor Steamboat, until Steamboat could take no more and fired back at the bigger opponent until SID screwed him out of a potential win. So while Steamboat has had a great match with a larger, much more dominating opponent in Vader, I’m still not overly convinced he could have THAT kind of match with The Undertaker. And honestly I’d put the “blame” more on Undertaker and how he works and how his character is as to why the match probably wouldn’t hit it on all cylinders. Both of them in their primes in a big match is still something I’d fucking love to see, more so with Undertaker as BIG EVIL, but a Streak match is out of the question for me tbh.


Mark Henry – Yep, like Flair, this match already happened. Back in 2006. And it was “meh”. However… picture this… 2006-current Undertaker Vs Mark Henry… from 2011. HALL OF PAIN. I was actually considering this for the top 10 list, but at the time I only had 9 guys on the list and while coming up with a 10th… I came up with 11, and had to cut someone, and unfortunately it was Henry. But only because the other 2 guys were more appealing. I’d still fucking pay to see this happen! Henry in 2011 once he turned heel was an absolute MONSTER. He’d always shown signs of being great, hell even back in 2006 when he originally faced Undertaker at WM, he was getting another push as a big monster heel and DID have some damn good matches (a couple superb matches with Rey, a better than their WM match with Undertaker on SD, and an incredible Benoit bout), but it wasn’t until 2011 that everything fell into place and he really was damn good on a consistent basis. He completely mauled guys like Big Show, Kane and Sheamus, took the WHC from Orton (beating him clean 2 PPV’s in a row) and probably would have gone to WM with the title had he not gotten injured. Imagine if he stayed healthy and made it to WM with the belt… only to face THE UNDERTAKER! Definitely something I would have loved to watch!


Razor Ramon – Dammit, this guy was ON my top 10 list… until someone brought up something about Japanese wrestling and BAM, I realised I forgot someone. So unfortunately poor Razor Ramon had to be cut. But hey, he’s going in the WWE Hall of Fame this year so it’s not all bad, right? Razor was one of my favourites as a kid. I grew up during the “New Generation” era of WWF and even to this day I’m a huge fan of that time period. Undertaker, Diesel, HBK, Bret, Owen, Yoko, Vader, Bulldog, 123-Kid, Bam Bam Bigelow and others, along with of course THE BAD GUY, RAZOR RAMON. Razor himself has said he’s a “punchy babyface” in that he used a lot of punches in his matches to start his comeback and to cut off heels etc. Undertaker is without a doubt one of THE best strikers in WWE history. Sure it’s something of a “cliché Michael Cole” line, but I’ll be damned if it ain’t true! So my idea for these two would be 1995-1996 Razor Ramon as a babyface against a 2002 Big Evil heel Undertaker! Undertaker can beat down Razor with HIS striking ability, then Razor can make his comebacks with HUGE right hands of his own to match Undertaker punch for punch. A simple formula, but with how both characters are and everything else they can do, I picture this being an incredible match. And hell, even a HEEl Razor Vs 2002-2003 babyface Undertaker would work wonders too! It’s a shame these two only had about 3 matches together, and were short (around 10 minutes) with no decisive finish, and only taped for VHS releases. If Razor had stuck around in 1996 instead of going to WCW, I definitely think this would have been a big PPV match at some point. Oh, what could have been.


Sting – What? WHAT? Sting isn’t on my top 10 list? That’s INSANE, right? So he’s just an honourable mention? Well… no. Not even that. Sting Vs Undertaker is not a match I would EVER want to happen, never mind at WrestleMania!!! Even in his prime (around 1992), I never thought much of Sting. Outside of the Vader matches, Sting just hasn’t done much worth talking about. The Flair matches were bad in my opinion. And uhhh… is anything really pimped outside of his series with Flair and Vader? He has 2 good matches with DDP on Nitro, one in 1998 and one in 1999 (the better of the two, though they are both extremely similar), and an incredible match with Regal in 1996… and that’s about it. His series with Vader, while I’d say Vader was the better man, wasn’t a carry job for sure (though any faults I tend to find with the matches are on Sting’s behalf). The Regal match was a 100% Regal carry job. So yeah, my thoughts on Sting are not high whatsoever. Which is why I don’t see the appeal of a potential match between the two. Sting in the ring kinda sucks, and his gimmick just never struck me as something that would mix well with Undertaker’s (his Crow gimmick of course, which is the time when everyone wanted the match to happen). Undertaker is basically a walking DEAD MAN who at times was downright EVIL AND DEMONIC. Sting was just… a regular guy who one day wore a black trench coat and decided to hang out in the rafters. Yeah… those sound similar… So between gimmicks that to me make no sense to compete against each other, and Sting never been all that good in the ring, this is absolutely a match I don’t think would have ever been good and should never happen. Sadly right now in 2014 there does seem to be a small possibility of it happening, I just hope if they do go ahead with a match they stay away from WrestleMania as it simply doesn’t belong there.




I’ve talked about some of the more “obvious” choices, now its time to get to the actual top 10!!!



The Undertaker (2006-Current) Vs Kurt Angle (2006)

This match SHOULD have happened at WrestleMania. In 2006, at the No Way Out PPV, Angle and Undertaker wrestled for the World Heavyweight Championship. Angle retained, but not without some controversy, so a REMATCH between the two at WrestleMania would have been absolutely perfect to conclude this little rivalry, especially after the incredible match they had at No Way Out. If you haven’t seen it yet, or don’t remember much about it, go back and watch that match. It’s awesome, right? Yup. Now imagine them doing that at WrestleMania! Even the Shawn Michaels/Undertaker matches would have a hard time competing with it. Instead, what DID we get at WM 22 that year? Undertaker in a mediocre casket match with Mark Henry, and Angle in a triple threat spotty mess with Orton and Mysterio, because Rey just HAD to win the title in honour of Eddie Guerrero. Which I’m not going to complain about too much because Eddie was awesome and seeing someone win the belt in his memory was nice, AND Rey absolutely fucking deserved a title run… but I just wish it could have happened at another time and place.

The crowd in Chicago that night were incredible, so just imagine them getting this match for the WHC. Both were babyfaces, both were at the top of their game, and both would have put on the performance of a lifetime. Angle as the Olympic Gold Medallist and Undertaker as the veteran who is ever adapting to keep up with the times and with new opponents and new styles. They worked those things into their No Way Out match WONDERFULLY, so having a rematch on the grandest stage of them all would have made them step it up a notch. As much as I dislike Angle most of the time, he had tremendous chemistry with The Undertaker, and I have zero doubts that this would have been in any way bad. Their No Way Out match for a long time was my favourite match ever (until I got around to re-watching the first ever HIAC and realised nothing even comes close to it lol), I can only imagine what I would think to a WM match between the two.



The Undertaker (2006-Current) Vs Chris Benoit (2003-2005)

Why did we never get this match? Why? Couldn’t we have at least had it on another PPV? Something? We DID get 3 matches between these two… but they all took place in 2000 when Undertaker wasn’t exactly stealing the show every night, and they were never presented as big matches. One on Raw, one on Smackdown, and then one at Rebellion, a UK “PPV” which was basically a house show they glammed up a bit, taped and made us UK fans pay £15 to watch lol. I would even have settled for a damn TV match on Smackdown in 2006/2007, as at least then they were really putting effort into big TV matches, with both guys having some tremendous TV matches with a variety of opponents at the time. Maybe we WOULD have gotten this eventually, had the whole incident in 2007 never happened, but it could have still just ended up as a TV match like Jericho/Undertaker (not complaining too much about that one since I was there)… but even then Undertaker and Benoit HAD wrestled before. The only way to go was a big PPV match imo. And yeah, Wrestle-fucking-Mania was perfect.

Match on paper would seem similar to Angle/Undertaker, with Benoit as the better “wrestler” on the match and Undertaker having to adapt his style to keep up and hopefully win. Only difference is… Benoit could have been much more VICIOUS. Less flashly kick outs and more narly, gritty brawling and mat exchanges, and probably some of the better “will The Undertaker TAP OUT?” moments ever. Because when Benoit locked in the Crossface you got the impression he could tear your damn head off if you didn’t tap. And that would have been PERFECT for a Streak match to add that much needed drama.



The Undertaker (2002-2003) Vs Genichiro Tenryu (1990’s)

Cannot believe I originally forgot about TENRYU. His addition to my list knocked Razor Ramon off, but you know what? It was fucking worth it. Take the GRUMPY OLD BASTARD version of Tenryu (which has been most of his career tbh lol), and take the babyface BIG EVIL Undertaker, and just let these guys PUNCH EACH OTHER IN THE FACE for an hour. Would rival the HIAC match as the greatest match of all times. Hell, heel Big Evil Undertaker would work two. Might actually work better. Heel Undertaker would go to greater lengths to try and KILL Tenryu, while Tenryu would just look at him in disgust and punch him in the fucking FACE. Unsure really what else to talk about with this one. If you are familiar with TENRYU then I genuinely hope you understand WHY I would love to see this happen. If you aren’t, then you’ll just have to take my word that it would be the greatest thing ever (while also looking up some damn TENRYU matches because you should).



The Undertaker (2006-Current) Vs Jake “The Snake” Roberts (1986-1988)

Fully aware that this happened at WrestleMania. But it wasn’t what it COULD have been had everything aligned properly like it could if I had this magical time machine thingy. Jake in 1992 when their match happened, wasn’t anywhere near the top of his game. His personal problems were, well, a big problem, plus he was leaving the company. They got very little time to work the match, and while I liked what they did, it’s still very disappointing when you know just how fucking good Jake can be and how incredible Undertaker can be too.

So I’d bring this version of Jake into say, 2008. With all the TV WWE had even back then, they could REALLY put a ton of effort into the build up. Start it early, maybe even in a similar way to how it happened back in the day, with Undertaker and Jake working together. Then do the turn, and it can all really get started from there. The promos would be incredible, and being able to do something every week on TV, with replays of it multiple times a week on other shows would just enhance their impact imo. Hell, honestly, I wouldn’t change the core structure of their original feud. It was great. They started off friends, Undertaker turned on him, and from there both guys tried to out do each other with the mind games. Only this time you’d have, as I already set, more TV time to build on it, better production, and both men are their absolute best too. And with THE STREAK being of such importance now too, they wouldn’t get shafted with a short meaningless match at WrestleMania.



The Undertaker (2006-Current) Vs Eddie Guerrero (2005)

This is another of those matches that we MIGHT have eventually got had Eddie not tragically died in 2005. They never had a singles match, in fact as far as I’m aware, the only encounters they had were a 6 man tag in 2002, and then the 4 way match at Armageddon in 2004. And that’s IT.

So we take Eddie in 2005 when he was the absolute BEST in the company at the time in terms of being an incredible heel character and still producing incredible matches (REY series!), and put him up against the best version of Undertaker for match quality and BAM, no way can this go wrong. Sadistic heel Eddie can talk up the Guerrero legacy, and put himself over as being the best in the world. He can tell us how he’s “been there and done that” with the WWE championship, so now he wants to go after something else to cement his name in history. And that something else would be THE STREAK. Eddie during the match could really channel that incredible heel character he had at the time, doing anything and everything he can to counter Undertaker’s size and power and to try and BEAT the Dead Man and end the Streak. Match wouldn’t even need to be No DQ or anything, as it would allow Eddie to play up on the “lie, cheat and steal” stuff, but not necessarily in a way that would make the fans cheer for him. It’s one thing during a Streak match for someone to hit a finisher and get a near fall, but imagine Eddie cheating like FUCK to keep Undertaker down and get near falls from that!



The Undertaker (2006-Current) Vs Mick Foley (1996-1997)

These two had one HELL of a rivalry back in the mid 90’s, producing some incredible matches. One on one, Buried Alive, Casket (house show), Hell in a Cell, and one on one matches that more resembled wild crazy No DQ brawls. Oh and that Boiler Room Brawl match… but the less said about that the better. And yet… no WrestleMania match? Huge missed opportunity there imo. WM 13 in 1997 would have been PERFECT for sure. A little re-booking her and there to keep the belt on Bret after the Final Four PPV, allowing Bret/Austin to be for the title, then switch Sid and Mankind around so we get Mankind Vs Undertaker, and the title titles match could have been Davey/Owen Vs THE MASTERS OF THE POWERBOMB (Sid & Vader). Hell I could probably write a damn piece on just re-booking WrestleMania 13 lol, but gotta stay on topic here; Undertaker Vs Mankind at WrestleMania!

So even though I’ve gone with a much later version of Undertaker, even if we stuck to the actual time in 1997, the match would have still been incredible. Undertaker and Foley had incredible chemistry together, and could have easily had a classic back then at WM. But bring that version of Mankind into a more current time against an even BETTER Undertaker, and during a time when THE STREAK is actually a thing and incredibly important, and you have the makings of not only a classic match but one of the better feuds ever. In fact, A couple of years ago I started writing a scenario for an Undertaker Vs Mankind WM feud, leading up to WM 26 I think it was a the time. I wrote out the first promo/segment for the build up but as with a lot of things I start, I just never finished it. The basic idea for the feud at the time was for Mankind to come out and talk about how he hates seeing Undertaker like this. No longer “on the hunt” like he was back during their mid-90’s feud, but instead content to wait for someone to come out and challenge HIM for a match at WrestleMania. So he would have to get Undertaker to challenge HIM instead, and the premise for the WM match wouldn’t be about beating the Streak, it would be about beating the living hell out of each other. Since then though, we HAVE had Undertaker switch it up and be the one to make the challenge, against Triple H at WM 28, though I think the way I envisioned it for Mankind would be WAY better haha. And yeah, that’s just the BUILD UP. The actual match? FUGGEDABOUDIT. An in shape, healthy (for his standards) Mankind Vs Undertaker at his very best, in a massively high profile match at WrestleMania built around the two of them destroying each other? PURE. FUCKING. HEAVEN.



The Undertaker (2006-Current) Vs Terry Funk (1989)

I’m sure (or at least, I hope), everyone knows about TERRY FUNK in 1989. The angle and matches with Flair, mainly. My idea for a Streak match with Funk is to take part of what actually happened in 1989 but tweak it for Undertaker rather than Flair. Funk could be on commentary or something for a big Undertaker match, say at the Royal Rumble. Undertaker wins, then does the whole “point at the WM logo” thing that everyone does nowadays, to show that his mind is now on WM and who his next victim will be. Cue Funk getting in the ring and congratulating Undertaker. Funk as a well known, well respected veteran would be the kind of guy who COULD get in the ring with ‘Taker and do that without getting a random Chokeslam just for the hell of it. Funk can then do a sort of improv interview with the Dead Man, asking him who he thinks the next Streak challenger will be… and that’s when Funk can “jokingly” throw his own name into the hat. Undertaker, upon hearing it, can just smirk at Terry, similar to how he did it to HHH during their encounter leading up to WM 27. And that’s what sets Funk off. He can laugh it off to begin with, then when Undertaker turns his back, BAM. Microphone to the back of the head followed by Terry beating the shit out of the Dead Man. Funk is a well renowned TOUGH SOB and Undertaker just had a match so it wouldn’t be hard to think that Undertaker would be unable to make a comeback here. Piledriver through a table, and the WrestleMania match is set!

For the match, little more needs to be done that to make it No DQ/Falls Count Anywhere or something. Funk as the crazed “old man” (OLD in 1989 lol… compared to what he is NOW?) resorting to using everything he can get his hands on to brutalise Undertaker. Undertaker, also being from Texas, probably has a world of respect for Funk and would be willing to make him look as good as possible, selling everything as great as Undertaker can sell it (which is like, world class levels of selling) and letting him get as much offence in as he wants. A punch exchange from these two would make my private parts all tingly. Just let them both have a big wild, crazy brawl, take it backstage, into the crowd, fucking everywhere. Would be unique for a Streak match for starters, and these two guys beating the hell out of each other in a variety of ways would be nothing short of AWESOME.



The Undertaker (2006-Current) Vs John Cena (2007)

This match could still actually happen. Not 2007 Cena obviously, but it could still ACTUALLY HAPPEN. And it kind NEEDS to happen. Cena is the one guy left on the roster right now who could challenge The Streak and make the outcome unpredictable. Something we haven’t had in quite some time. Cena is known for being “Superman” who overcomes all the odds no matter what, and is a guy who WWE go to great lengths to push even further and put him over even more. Which makes him the perfect WM opponent for The Undertaker, but despite everything, in the back of all our minds, we will be thinking “yeah, Undertaker’s streak is probably never gonna end… BUT WWE might actually consider letting Cena end it…”. So while most of us DO get caught up in the moment watching WM live as someone hits their finisher on ‘Taker… I guarantee EVERYONE will be caught up in the moment as Cena locks in the STFU or hits an AA from the top rope. The atmosphere in any arena for this match would be electric, which would only ADD to the viewing experience. I just hope we really do get it soon, certainly over something like a Sting match.



The Undertaker (2006-Current) Vs Vader (1992-1993)

They had a few matches in 1997, but in all honesty I was disappointed with them all. WWF Vader just wasn’t VADER. But take the early 90’s WCW champion Vader, and put him against Undertaker (from virtually any time period tbh), and I think it’s almost guaranteed to be far better than anything we got in WWF 1997. Vader as the big monster heel who wants to CRUSH Undertaker, and Undertaker as the legend fighting to keep his Streak alive against one of the biggest threats ever. I’d imagine the match to be somewhat similar to the 08 matches between Undertaker and Big Show; just huge guys trying to cave each other’s faces in. Vader being able to really let loose and not be toned down by WWF would make Big Show look like a CHUMP. Undertaker firing back with HIS strikes would be awesome to see, and of course his selling of Vader’s offence would make this whole thing incredible to watch. Oh, and imagine the near fall we could get from a fucking VADER MOONSAULT!!!



The Undertaker (2006-Current) Vs Jerry “The King” Lawler (1980’s)

Ok, I know what some of you must be thinking; I’ve finally lost my mind. Right? I guess it all depends on how much (if any), you’ve seen of Lawler during the 80’s. Unfortunately a lot of people today, when they think of Lawler, they only really know him from his WWF run, either in the ring (which honestly never produced much goodness) or commentary (which has been dreadful ever since he returned after Survivor Series in 2001). But for those who have seen his work in Memphis and the like from the 1980’s, you should know just how fucking GREAT Jerry Lawler was (and still is, he CAN still produce greatness today). He could be the ultimate underdog, fighting from underneath against a monster heel, or he could be one giant PRICK heel who would cheat every chance he got behind the referee’s back.

A match between these two could be absolute, undeniable MAGIC given the right circumstances. Went back and forth for a while with myself (as I often do. I’M NOT CRAZY) as to which Undertaker I should use. Big Evil Heel from 2001-2002 was sooo close to being picked for this, but in the end I went with 06-current as he’s been at his BEST in the ring during this time. However, I’d make Undertaker the HEEL for this. Lawler as the uber babyface fighting back against a demonic heel Undertaker is just… just… ORGASMIC. Book the match similar to the epic Loser Leaves Town match between Lawler and Dundee from 1985, with a heel Undertaker just punching the shit out of Lawler. More of a boxing match than a wrestling match. Undertaker just continues to punch the shit out of Lawler, busting him open, targeting an eye, and the crowd would be 100% behind Lawler making that big comeback. And when he does, the roof would blow off any damn arena anywhere in the world. All it would take is a well placed punch to create enough space for Lawler to rest for a few seconds and throw ANOTHER punch. And from there, the straps can come down and we have ourselves the hottest finishing stretch imaginable for a match. Hell, stick this match in the Mid-South Coliseum during the 1980’s and you’d have the most MOLTEN HOT crowd ever too. Well I’m just gonna shut my eyes and imagine this entire match…. ahhhhh.


So there it is! My list of the Top 10 Streak matches to Never Happen! Hope you enjoyed reading it, and I’ve love to hear YOUR top 10 list too! So feel free to post a comment below!

One response to “WrestleMania Week – Top 10 Streak Matches to Never Happen!”

  1. Cjack says:

    Awesome column man, you really took this idea and ran with it.

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