10 Wrestling Dream Matches That ACTUALLY HAPPENED... But In The Wrong Era

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From Sting vs The Undertaker to Samoa Joe vs William Regal, these are 10 Wrestling Dream Matches That ACTUALLY HAPPENED... But In The Wrong Era.
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Cultaholic provides video coverage of professional wrestling - including WWE (including WWE Raw, WWE SmackDown, NXT and 205 Live), AEW, IMPACT Wrestling (formerly TNA), NJPW, ROH, and more with daily news updates, reviews, lists, highlights, predictions, reactions, podcasts and much, much more.

[@Cultaholic]

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[@sirprintalot]

okay

[@gsandison1]

Blink twice for help

[@Lenoh]

I just recall the “We have a Lord Of The Ring!” call from Schiavone on WCW.

[@kenrickeason]

WWE being WWE had Ric Flair and Hulk Hogan in the same damn company and did not capitalize on it.. WWE left money on the table but hey it's WWE..

[@kenrickeason]

Shawn Michaels vs RVD would have been a perfect match..

[@the_clownprince]

The amount of sarcasm in the paid sponsorship was palpable

[@Blocparty01]

He's definitely playing it!

[@shawnmcconnell3851]

You tried so hard to be excited about backgammon.

[@ThomasCassonActor]

Backgammon is rad 🔥 I hope he plays POG's next

[@oddishhonor]

@@ThomasCassonActor it’s jax or nothing for me

[@stevenpagnani7005]

I never understood that game

[@furrynipples2698]

I totally believed he's playing

[@austinwilliams7919]

I'm more of a mahjong guy myself

[@FoxeyeValkyrie]

I cannot wait for the Backgammon 12 hour stream coming up on Twitch.

[@franklingoodwin]

Backgammon U Next Tuesday (BUNT) 😄

[@timfarner41]

Way to put over the commercial , bud lol

[@leejames1839]

Are you for real must be 155years old

[@franklingoodwin]

Mean Mark vs Surfer Sting was my WCW era because I'm old AF 😂

[@neighslayer768]

Ricky Steamboat fought Bret Hart on the house show circuit leading up to WrestleMania 2. Imagine if we got The Dragon vs. The Hitman during the former's return in 1991?

[@CommodoreFloopjack78]

"...Backgammon is a COOL board game!" You, my unreasonably enthusiastic friend, are the first human being in history to utter that sentence. Congratulations.

[@rekmadethebeat]

I read this comment before I actually saw the video and after hearing it that made this 10 times funnier

[@CommodoreFloopjack78]

@@rekmadethebeat 👍👍👍

[@neomimzyneomimzy5095]

I will never get over the fact that STING vs. THE UNDERTAKER didn't happen, when Sting was finally in WWE.....a match against each other or let them team....anything....but we got NOTHING!

[@moopert86]

Who needed Taker Sting when we could get the incredibly stupid Mania match between HHH and Sting no one ever wanted.

[@vampirascoffin870]

Thank you facts!!!!!!!

[@onemuststand7353]

What's worse is that they turned what was a halfway decent authority vs vigilante story line into a Monday Night Wars feud that nobody really wanted anyone to win.

[@siegfriedc2332]

@@onemuststand7353 This. Absolutely. I initiqlly thought Triple H was a good first opponent for Sting; someone for him to beat before facing Taker next year. As u said, even the build up made it seem sensible that he'd win. But they just had to turn it into a monday night war rehash, which made zero sense because Sting was more known for being an enemy of the nwo.

[@georgemetcalf8763]

How Flair didn't get to run in and the crowd wonders who he'll attack is shitty booking.

[@Rwp019]

It could have been better and got a bigger Pop if the NWO to come out would have been the Wolfpac. Also, Flair coming in and leaving everyone wondering whose side he would take WCW or His Evolution stable mate would have been solid gold. That said Sting should have won as a build for a Taker v Sting Match but this was about Mcmahon wanting to stroke his ego and Bury WCW again and Not what would have put asses in the seats and been good for the business

[@mikemullens7733]

The hilarity that Lord of the Board are the sponsor hahahahahaha

[@AmariieMaerthos]

It's like they're TRYING to take the piss outta No Rolls Bared

[@unfixingbowl5454]

They really wasted Brock/Lashley to advance a storyline

[@unfixingbowl5454]

@@ssj2camaro21 the first one is the one they have to make count

[@losnamerales3403]

@@unfixingbowl5454 real talk it's one of those rare matches that are perfect on paper all they had to was -follow- -the- -train- no I meant make good match out of the spetical, tell them a few good spots that are supposed to happen and have a narrative for the match itself then improve from there 💯

[@PedroMartinez007011930522]

I would like to see Brock vs Miz

[@JagerLange]

I like how Adam put more effort into this ad than the real endorsement.

[@taalash]

“I’m definitely playing it!”

[@diesel101raw]

RVD vs Shawn Michaels was actually Perfect in 2002 just sucks we Never got a Rematch. Huh ?

[@evrbody]

If Shawn hadn't lost his smile in 1997 we could've had HBK vs. RVD during the ECW invasion.

[@MORT666]

how do you work that out? He Was not involved in the Invasion angle because he was forced into Retirement in 1998. It had absolutely nothing to do with him losing his smile.

[@matthewlieberman7474]

@@MORT666 there was another ECW invasion in 1997

[@evrbody]

@@MORT666 I'm talking about when ECW wrestlers appeared on Raw in 1997, most notably RVD. It was an angle to help ECW get exposure and promote their first PPV, Barely Legal.

[@MORT666]

@@evrbody i Didn't even think about that one, but there was no interpromotional matches during that Invasion so they still wouldn't have faced off

[@ericmonaco4509]

Or if Shawn hadnt broken his back at Royal Rumble 98 and was still wrestling in 2001

[@diesel101raw]

Nah I'm actually Glad CM Punk vs Eddie Guerrero happened when it did. It just sucks we didn't get a Rematch because Eddie Guerrero Passed Away. Imagine Eddie vs Punk in 2006-08 when ECW came back

[@kenrickeason]

@@xMikeyHardyx You do know Eddie got some of his first exposure from the Original ECW?? But nonetheless CM Punk vs Eddie Guerrero would have been nothing but money..

[@MikeLaundry]

Best passive aggressive ad read since the great Raid Shadow Legends calamity of 2019

[@connorharkins3721]

'good luck because I'm definitely playing it' been a fan for years and that ad is one of the best things I've seen you do. God bless you Adam Pacitti 😂

[@The_JustJoshing]

Undertaker vs Goldberg. Should’ve happened 15 years earlier

[@timothygraham4304]

It should never have happened. The styles don't mesh well. Having Goldberg in a match longer than 2 minutes, isn't going to work, and having Undertaker in a match shorter than his entrance, would have people rioting!😂

[@The_JustJoshing]

@@timothygraham4304 Actually that’s true haha

[@timothygraham4304]

@@The_JustJoshing 😂

[@kpat92]

Worst match in history

[@diesel101raw]

@@timothygraham4304 I say 2002 I Wished it Happened

[@dariselectricincorporated3226]

Never got to see Shawn Michaels vs The Rock

[@titanhades4331]

Cause Rock refused to ever work with him.

[@losnamerales3403]

@@titanhades4331 I can understand why, the clique gave him a hard time when he started and only thought to do a match once he was really over and looking more like a superstar 💯

[@dariselectricincorporated3226]

@@titanhades4331 yeah I’m aware. Apparently HBK also allegedly insulted The Rock’s grandmother? Or something like that

[@zakarypembleton9666]

I came for the wrestling but STAYED FOR THE BACKGAMMON

[@jacksurvivalwolf9671]

Adam actually makes me want to play Backgammon, i've been loving the over the top sponsorships lately

[@djlune]

No disrespect to William Regal which he's one of my favorites but I think Samoa Joe vs Tazz would be a better dream match #justsaying

[@greenelf12]

Did it happen though?, because these are dream matches that did actually happen at some point. If it was just a dream match list of course it would have been in There.

[@djlune]

@@greenelf12 from my knowledge No it didn't happened

[@taylorfe88]

That would be awesome!!

[@kenrickeason]

I agree..

[@cheezeofages]

Speaking of Regal, his recent firing and people hoping for him to get a job in AEW made me really wish a Regal vs Arn Anderson match could happen. That would be a banger if they were in decent ring shape. Oh wait, a quick search reveals that happened in WCW! I'll watch that.

[@leftwingdragon6235]

I just want him involved in the booking, training because he would be great in that role in AEW.

[@WilDBeestMF]

@@leftwingdragon6235 I'd LOVE to see Regal do something with the NWA. I feel like he would be superb in and around there with his knowledge.

[@deadbydefiance9341]

Adam is definitely playing it and so are all of us 👍

[@ryzotheraver828]

The sarcastic ad was amazing 😂😂

[@kaputa814]

Punk has the utmost respect for Eddie and its because Eddie was not only an amazing wrestler but a great human being. Props for the IC title match even if unfeasible, it gave punk his endorsement. Punk has stated learning so much from eddie.

[@agentorange1156]

Owen was so good, but we missed his prime! He had 2 years left and then he would have retired. In those 2 years we could have had classic matches and programs with Owen Vs Benoit Vs Guerrero Vs Edge Vs Christian Vs Angle Vs Malenko Vs Jericho Who knows, maybe even in this alternate reality he may be able to smooth things over with Bret and the wwe in 2001 or something.

[@michaeljay3044]

Did he said he was going to or are u just saying this?

[@agentorange1156]

@@michaeljay3044 yeah he said around that time that he had 2 years left on his deal, that he was going to retire at the end of it. Jim Ross confirmed it on his podcast as well

[@christopheroliver3721]

Classic LOD vs taker/Kane. I would have love to see, “Dream Matches”

[@seanchan4478]

I don't think it's said enough so imma say... Chris Jericho fought Eddie Guerrero in WCW

[@franklingoodwin]

People say it all the time

[@seanchan4478]

@@franklingoodwin but it's still not enough

[@franklingoodwin]

@@seanchan4478 What's enough? People are saying it happened. That's really all that should matter

[@seanchan4478]

@@franklingoodwin well... This is the first I'm hearing that people say it all the time, and it wasn't on this list. Based on this information alone, I would say one more time, the answer to your question is once more. And then never spoken of again

[@franklingoodwin]

@@seanchan4478 It sounds like you wanted to be the one to say it rather than other people say it. I'm guessing you're THAT guy 😄

[@ben6993]

Fair play for you desperately trying to sell Backgammon 🤣

[@greenelf12]

It's better than chess.

[@JaimeD.]

So...these matches are a big *WHAT IF...* which it can only happen in a WWE video game in the present. Curse them for not taking those opportunities when they presented themselves.

[@yankeekill]

No mention of John Cena vs The Undertaker? I remember seeing it on Smackdown of 2004 before Cena became a huge star and Undertaker was feuding with the Dudley’s. The match at Wrestlemania 34 was about 2 and a half minutes, but if they had a match 10 years earlier, especially if Cena hadn’t lost at Wrestlemania, it would have been huge.

[@ancientmonk8742]

Brock lesnar vs Batista.. Only fought once in OVW...🥲🥲🥲

[@ezekielluna6265]

Twice and a 2003 dark match on the main roster

[@ancientmonk8742]

@@ezekielluna6265 Did they? I only remember them crossing paths in the royal rumble where brock won the rumble

[@ezekielluna6265]

@@ancientmonk8742 yea it was a dark match so it wasnt televised either house show or to entertain crowd before or after a taping. I only know after looking it up cause i really wanted that main roster match. In ovw in the match they taped you can hear cornette talking about a rematch at some fair or something but theres no footage they didnt tape it i guess

[@armin38822]

At every stage of his career,Chris Jericho always looks in his prime.

[@ReturnoftheDILF]

The way you take the piss out of all your advertisements is brilliant

[@omarijustomari3115]

Call me a crazy conspiracy theorist but I don’t think Adam is gonna be playing backgammon

[@diesel101raw]

Stone Cold vs Randy Savage in 1997 wudda been Perfect

[@artirony410]

AJ Styles and Hiroshi Tanahashi in TNA, although they did also work together later in NJPW

[@johnalbent]

This is really well done. Thank you 🙂

[@master-_-beavis5261]

Austin came to WWE with a chip on his shoulder. And that alone, changed the way wrestling would be seen thru the rest of the 90s.

[@caseyhastings9219]

I love Adam doing these paid promotions, because I'm so used to Adam sounding sarcastic/insincere that it ends up coming off as parody instead of an advertisement.

[@greenelf12]

I'm undecided on if he actually plays the game or not.

[@LuciferTheDogKiller]

My ultimate dream match is a triple threat match between The Rock, Shawn Michaels, & Sting.

[@emlynbarnden1229]

This might be the funniest advert ever

[@ashley_bell]

Adam’s ads are everything.

[@derrickcannon2191]

Hogan versus HBK happening earlier is a full on wrestling butterfly effect for the company, HBK, possibly Bret Hart and others at the time in the promotion.

[@midsectionmark8956]

I’m surprised Batista vs Brock in OVW isn’t on there. Plus i enjoyed seeing those two in the ring. To bad they didn’t do it again in a big match feel.

[@VMP666]

God, I could watch just a compilation of Adam's HONEST TO GOD opinions about their sponsors. Lova ya mate

[@baloothepibble8421]

The best video topic idea I’ve heard in months

[@AndrewJShirley]

"Coz WCW, innit" DEAD 😂😂😂😂

[@philg7196]

No one gonna talk about Eddie Guerreros race listed as white on his arrest report. Can totally see Eddie saying “Cant u see I’m white holmes” when asked his race at intake😂

[@losnamerales3403]

Using the "we lie we cheat we steal" stereotype/tactic to his advantage in a whole different way 😂

[@TheReignofHorror]

Undertaker vs AJ Styles. If that match had happend only few years earlier (either at Wrestlemania 32 or 33) we could have probably seen one last decent if not good in ring match out of the Undertaker, instead of the lackluster match with Shane or the awful match with Roman (AJs matches with Jericho and Shane were good, but nothing to write home about). The match they had in Saudi Arabia was more of an angle and while the boneyard match was good it was not really what I was looking for when I wanted to see this match.

[@BiggieTrismegistus]

I always thought AJ Styles versus Shawn Michaels would have been absolutely amazing. So would AJ Styles versus Rob Van Dam.

[@thoroughbredunderdog]

Man I just know there is gonna be sequel to this list with Batista vs Brock and Kurt Angle vs Owen Hart

[@dna507]

A weird time to start advertising something called Lord of the Board.

[@nik68]

Once you go backgammon, you never go... back... gammon...

[@shaunsantos3140]

Cultaholic have sold out too the backgammon overlords

[@casualgerman1949]

Great topic! Even long time fans/hard core fans can forget that The Undertaker worked in WcW before he became the Undertaker. And who else worked there? ;-)

[@ArthurKillingsworthJr]

That advertisement was brutal

[@JitteryJackanape]

another one for me is Cena vs The Undertaker. I know it happened in 03, but i would have loved a full fledged feud between the two of them once Cena became the top star. Their brief Mania 34 match also happened way too late in Undertaker's career to never be able to deliver compared to matches Undertaker had with Shawn, HHH and Punk. I think around 2012-2015 would have been the "best time" But 07-09 would have also been good. They were just always on other rosters competing for that brands top championship. Shame really.

[@theswitchblade2683]

Actually undertaker said he was in the best shape hed been in for years when he had that match with cena and wished they couldve had a proper match as he felt he couldve gone for a full 30 minute dream match like everyone wanted, he knew it wouldnt have been as amazing as them in there prime couldve been, but it wouldve been better than him playing the hits for a quick squash match

[@JitteryJackanape]

@@theswitchblade2683 yeah and mania 34 was in 2018. In 2015 he was still doing banger matches with Brock Lesnar. But if you look at the matches he had at that time they were short or not great. Cena also was not available to do something like that due to other commitments he showed up as a guest appearance basically. 2017 his match at Mania with Reigns. Botches but not the worst he'd ever done. 2018 - Super Showdown and Tag with Kane against DX - horrible. 2019 - Goldberg, horrible. Tag with Roman at Extreme Rules against Shane and Mcintyre, carried. 2020 - SuperShowdown Gauntlet not great but AJ helped him, Mania 36 a great cinematic match.

[@Atomykpimp]

Chris Jericho vs Sabu was amazing!

[@sorenutpal6091]

Seeing shield reunion in my lifetime is my top wwe dream

[@ReasonablyHilarious]

Here are some dream matches i wished happened or want to happen: Aj Lee vs Alexa Bliss Aj Lee & Alexa Bliss vs Sasha Banks & Paige Aj Lee vs Charlotte Aj Lee bs Bayley Dana Brooke vs Charlotte Charlotte vs Beth Pheonix Nia Jax vs Kharma Naomi vs Melina Michelle McCool vs Charlotte Lita vs Paige The IICONICS vs Laycool The IICONICS vs The Bella Twins Samoa Joe vs John Cena CM Punk Vs Aj Styles CM Punk vs Kevin Owens Edge vs The Fiend Sheamus vs Brock Lesnar Triple H vs Aj Styles Edge vs Kevin Owens Jericho vs Finn Balor Ryback vs Goldberg Batista vs Brock Lesnar Alberto Del Rio vs Eddie Guerro Daniel Bryan vs Chris Benoit Austin Theory vs John Cena Keith Lee vs Braun Stroman Keith Lee vs Big Show Kurt Angle vs Daniel Bryan Shawn Michaels vs Aj Styles RVD vs Riddle The Rock vs Shawn Michaels Undertaker vs Sting

[@RacerC45]

I wanted to see a dream match between Asuka and The Undertaker before he retired.

[@Lenoh]

> You are now aware that Sting has beaten BOTH of the Brothers Of Destruction

[@stevenrose86]

See Adam, this is why nobody pays you to do sponsorships. You need to tone down that sarcasm 😂

[@Assassin-ys5vw]

HHH ruining dream matches even before they where dream matches not once but twice is the most hilarious part in this video 😂

[@Jimbo_Ka-Blamo]

Omg that add read 🤣😂

[@PedroMartinez007011930522]

I would’ve loved to see Rey Mysterio vs The Rock, Hulk Hogan or Stone Cold Steve Austin

[@johnmirabella1329]

I saw Hogan face Bret Hart in a WCW house show in Tallahasee, Florida back in 1999 and I had ring side seats too

[@Blocparty01]

Backgammon is soooo cool!

[@judasblackheart2651]

Ah yes, I love a good dream Mathc

[@CWD632]

Holy fuck you went hard in the paint for backgammon.

[@vampirascoffin870]

Helloooo what about kurt vs mr.perfect??? Should have happened at wm x8!!!!! Sorry kane

[@danpettitt7012]

Bruiser Mastino was also a name used by Mantaur outside of WWE

[@madant22]

Wrestlers never mention these matches in interviews. I would love to see them mention there recollection of those matches in their interviews more often give us some insight of these dream matches that happened at the wrong time: or I should say happened on a smaller scale.

[@Walkerman404]

Shawn Michaels vs RVD happened at a good time, it was just used to further the Michaels/Triple H storyline.

[@perchance5066]

I'm just here for the adverts now.

[@ARRANH0UST0N]

came back to watch this video just for the backgammon

[@kashmere7980]

Guerrero vs punk vs mysterio featured on cm punk dvd (not affiliated with wwe) and it was fooking quality.

[@Matthew.J.G.L]

Cultaholic! I have a suggestion Make an every hall of famer ranked from worst to best I guess it is good

[@Matthew.J.G.L]

Wrestler hall of famers to be exact

[@thesfdoctor3603]

Hurricane vs AJ Styles is a dream match that happened (ironic, but not so much)

[@ayushkataria7983]

Lots of love from Amritsar

[@scootinand]

When Sting was in WWE, they should have main evented Survivor Series in a 5 on 5 match with him and Taker as captains, with the stipulation that if their team lost they would have to retire. Would have protected both older guys (not that Sting needed it as badly as Taker did at that point) by putting them in a tag situation where they could rest, and they could send Taker out on the show he debuted on

[@videofinder88]

Brock vs Batista is another one

[@andyq524]

My dream match has always been RVD vs HBK in a ladder match.

[@djam-wc8hh]

Batista vs Goldberg would be intriguing now

[@schockeddog6934]

I'm gonna just assume your trolling

[@schockeddog6934]

Personally I never understood the whole dream match stuff. For me as long as it has a good story I'm I'm. Especially if it has a real hatred feel to it. Like the Matt Hardy & Edge or Shawn Michaels & Bret Hart for example. How about a video of the top most heated rivalries

[@captaincharisma6306]

My dream match is Christian vs undertaker

[@gu3liooo159]

The Eddie Guerrero and Owen hart hittin hard asf rn😔

[@sinister2509]

Bret Hart vs Mitsuharu Misawa. That match did happen, but it was unfortunately when Misawa was working as the poorly received Tiger Mask II.

[@jeebranali3156]

Batista vs Brock Lesnar?

[@rockthered8141]

Well, technically if you count Sting's tag matches on Raw, he competed in 4 matches.

[@petebotGSD]

Pacitti advertisements = wonderful

[@tkx6347]

One More Dream Match Sting & Darby Allin vs. The Brothers Of Destruction

[@SeasideDetective2]

One arguable example that wasn't on here was Hulk Hogan vs. Andre the Giant at Shea Stadium in 1980. Counting WrestleMania III, of course, we got TWO matches out of them, but the true dream match between them would've probably happened in 1984 or '85. As it was, the two of them traded both wins and face/heel alignments between the two matches.

[@joekoe97]

Owen would've been perfect for smackdown. Imagine him in the ruthless aggression era.

[@SirDankleberry]

The fact that WWE denied the Sting VS Taker match proves they're out of touch.

[@losnamerales3403]

Bautista vs Goldberg could been good but a better idea would be a tag team run from them with the name... "Da Manimals" basically squash match annihilation in trunks 💯😂

[@c.d7016]

Hey Adam, lay off the kush and those dreams should come back ;)

[@ancientmonk8742]

Adam selling mobile games is the best..