The 10 Best Wrestlemania Matches That (Damn It!) Never Happened

While Wrestlemania has given us memorable moments of fan-favorite stars finally getting their due, some ships sailed by.

Some matchups never happened. For their marquee value, shock factor and (possibly) anticipation of a great match, they were most likely considered as potential scenarios for “The Show of Shows”.

Hopefully, most of these would have had Jim Ross calling the match and not Michael Cole, David Otunga, Byron Saxton and/or Booker T.

Which of these would you have liked to see the most?

1 – John Cena vs. The Undertaker

When John Cena was still at the height of his super push and The Undertaker had his Wrestlemania Streak, this would have been a stellar matchup.

On one side, the man Vince McMahon promoted more than any other. On the other side, the unbeaten Wrestlemania phenom.

Regardless of the victor, considering the verbal, acting and storytelling skills of both men, it’s easy to imagine a very well-done build-up…

… and a match where the fans would collectively gasp on every near fall, as Taker came close to “burying” (double, maybe even triple pun intended) Vince’s chosen son or Cena was on the verge of becoming Public Enemy #1 for slaying The Undertaker’s Streak.

I can see the “IF CENA WINS, WE RIOT” signs.

Why It Didn’t Happen¬†(Speculation): Creative decision, as other matches were considered priorities. After all, Taker did wrestle Mark Henry and Shane McMahon. Where the hell do you fit Cena into this docket? In fairness, the argument can be made that Cena and Taker’s star power is better used by being placed in different spots on the card. Like wrestling Mark Henry or Shane McMahon.

2 – Bret Hart vs. Shawn Michaels II

After Shawn Michaels won the much-acclaimed Wrestlemania XII Iron Man Match or, as HBK called it (twice) in his reunion with Bret Hart…

… The Hitman’s return in the Winter seemed to be aligned with the rematch being booked at Wrestlemania XIII. Shawn would have his detour in Sycho Sid (who could forget those epic confrontations?) and Bret would take time out from his busy workman-like schedule to give a promising prospect named Steve Austin a heated rivalry and a coming-out party.

But, by March, everything would be geared toward Hart vs. Michaels II. Given how the first instalment was an instant classic, imagine Bret Hart winning Round 2, reclaiming the WWF World Title and immediately setting up the rubber match.

That would have been must see.

Why It Didn’t Happen: Shawn Michaels “lost his smile”. While he stated that he was injured and his future as a performer was in peril, both pundits and insiders like Bruce Pritchard have recognized that, with this being the height of HBK’s “Prima Donna Age”, he may have opted to vacate the title and save himself from what he perceived would be a damaging loss to The Hitman – a tactic he resorted to more than once.

Contrary to legend, Shawn kept his smile. Fans (and Bret) did not.

3 – The Rock & Ronda Rousey vs. Paul & Stephanie McMahon

At Wrestlemania 31, the table seemed set. The Rock was slapped by the Emasculator General, but found Ronda Rousey in the front row to incite a face-off between themselves and Triple H and Stephanie.

Ronda Rousey, at the height of her UFC fame, came across as a giant star and dominated the action in a segment clearly built to put her over.

The marquee value and the storyline setup were clearly there, but the trigger was never pulled.

Rousey would only defend her UFC title one more time, in August, before losing to Holly Holm in devastating fashion in November.

Why It Didn’t Happen (Speculation): Rousey’s loss to Holly Holm was devastating to her star power (not just for the loss, but for what was perceived to be comeuppance for berating and provoking Holm at the weigh-ins) and her mental state, as she mostly went into seclusion after that fight. Should Ronda have won, perhaps this major tag team attraction would have seen the light of day.

4 – Randy Savage vs. Shawn Michaels

In 1992-93, as WWE moved from the Hogan-Warrior-Savage generation and into the Hart-Michaels era, The Macho Man knew one thing: he wasn’t done.

In fact, he was still more than capable of putting together stellar performances.

As WWF tried to settle Savage into a color analyst role, he pitched to have a long-term feud with Shawn Michaels who, according to Savage’s younger brother Lanny Poffo, was hand-picked by Randy for one last Savage-Steamboat-level hurrah.

If you know these two performers – from their wrestling technique to their talking skills – you understand how big of a candy was removed from our collective mouths.

Why It Didn’t Happen: Vince McMahon was adamant to move on to a younger generation and insisted Randy Savage be only a color analyst, regardless of how much gas he felt he had left in the tank. Macho rode his car over to WCW, taking his Slim Jim sponsorship with him which, according to Eric Bischoff, made Randy an investment that immediately paid for itself.

5 – Hulk Hogan vs. Roddy Piper

This could have easily been the main event of the very first Wrestlemania.

In 1984-85, at the pinnacle of Hulkamania, Hulk Hogan was as red hot as a babyface has ever been in the wrestling business.

But every great hero needs a villain up to the task. Lo and behold: “Rowdy” Roddy Piper. A man you’d have a tough time arguing out of any “Top 5 Best Promo Ever” ranking, whose specialty was to make you believe in what he said, while getting you to invest in the story he’s telling.

It was a natural Wrestlemania closer. However, their feud never had a decisive finale.

Why It Didn’t Happen: At the height of WWF’s rise in the Rock’n’Wrestling era, Vince McMahon opted for a tag-team main event between Piper and associate “Mr. Wonderful” Paul Orndorff against Hulk Hogan and hot celebrity Mr. T, of Rocky III and A-Team fame. Hogan and Piper would have 2 televised matches, but they both ended in DQ wins for The Hulkster, as the objective seemed to be to keep the house show business going, which meant keeping the Hogan/Piper feud going.

6 – Eddie Guerrero vs. Shawn Michaels

What could have happened in a clash between two of the world’s most well-rounded wrestlers?

Both Eddie and Shawn were very compelling acts both in the ring and on the microphone and, even in mere theory, it’s easy to predict that their in-ring styles would mesh well.

Wrestlemania would have been well-served with a 20-minute match between Latino Heat and The Heartbreak Kid after a properly set up feud. Imagine Shawn Michaels reacting to an Eddie Guerrero cheating attempt. Maybe even responding in kind. Maybe Eddie jumps Shawn from behind on a Raw segment and hits him with some Sweet Chin Music.

If there was such a thing as an easy 5-star feud, this would be it.

Why It Didn’t Happen: WWE was working toward this matchup as a Raw vs. Smackdown match at Wrestlemania 22, in 2006. However, Eddie Guerrero passed away in November of 2005, which pulled fans away from not only this match but one of wrestling’s most able hands.

7 – Bret Hart vs. Stone Cold 2

Discussed as the possible main event of Wrestlemania 14, this match would have been a very fitting end to the Austin/Hart feud, as Austin never managed a clean victory over The Hitman in their heated storyline.

And, while having Austin defeat Shawn Michaels at the “Granddaddy Of Them All” certainly served its purpose (help launch Stone Cold into the stratosphere), a victory over his biggest nemesis would have been the ideal championship conquest for Austin.

Bret Hart put Austin down at Survivor Series 1996 in his first outing since his Iron Man Match loss to Shawn Michaels at Wrestlemania that year. He also defeated him at Wrestlemania 13 in what Austin himself calls his most memorable match. Austin would defeat Bret by DQ at “In Your House: Revenge of The Taker”, but never got his pinfall win.

Which meant said pinfall win was being saved for when it counted the most: Wrestlemania.

Why It Didn’t Happen: Following the Montreal Screwjob at 1997 Survivor Series, Bret Hart was neither WWF Champion nor under contract with the company, having made his WCW debut shortly after, which left then-champion Shawn Michaels holding the title until Austin’s big moment.

8 – Sting vs. Undertaker

After WCW was purchased by WWE, Sting was one of the few talents that ended up not joining WWE. His contract, a very lucrative one, wasn’t formally signed with WCW, but with Time Warner, as was Hogan’s, Nash’s and those of other major stars.

And WWE wasn’t willing to pay these stars enough to either buy out their Time Warner deals or get off the couch, where fat WCW checks kept appearing.

This meant that, as Sting appeared for WWA and later TNA under short to medium term contracts, we all had a yearly “Is Sting coming to WWE” conversation.

And, given Sting’s “Crow” character, The Undertaker always seemed like one of – if not the most – intriguing matchup for Sting.

But Sting kept re-signing with Dixie & Company. And the two were apart for the longest time and unable to fulfill a dream match of intense showmanship, where one can predict a strong buildup with both men trying to outpsych the other.

Why It Didn’t Happen: I can only speculate that it didn’t happen for a long time because, as stated above, Sting kept re-signing with TNA. At Wrestlemania 31, when both men were in WWE and available, it seems it was a creative decision to pair them with other performers: Taker took on Bray Wyatt and The Stinger lost to Triple H… and shook his hand after The Game hit him with a sledgehammer. As any normal person would.

9 – Bret Hart vs. Randy Savage

The Hitman and The Macho Man were two of WWF’s most talented and bankable stars in 1992-93. Savage had become WWF Champion at Wrestlemania 8, a card that also saw Bret Hart win his 2nd Intercontinental Title, with a win over “Rowdy” Roddy Piper.

These were two master storytellers who only got a chance to wrestle each other at a 1987 Saturday Night’s Main Event and in WCW, at the 1998 edition of Slamboree.

And, while one can argue Savage had lost some steam in 1998, he was still in top form in 1992-93, even though Vince McMahon was (as mentioned in #4 of our list) committed to phasing out Randy Savage, as part of a push for younger wrestlers.

For the record, relegating a fully functional Macho Man to commentary duties is a decision whose stupidity is only beaten by the creation of an alternative football league.

This matchup would have done wonders for Bret Hart’s main event credibility, as Savage as part of the bigger names of his WWF generation, second only to Hogan and, perhaps, Ultimate Warrior.

To defeat Savage at Wrestlemania 9 in a masterpiece of storytelling – which both men were more than capable of delivering – would have made Bret Hart’s progression an even bigger story of success.

Why It Didn’t Happen: Savage dropped the title to Ric Flair… who then left WWF to go back to his more natural WCW/NWA environment. Bret Hart ended up being chosen to relieve Flair of the WWF strap, but never got around to facing a challenge from The Macho Man, who only served as a color analyst at Wrestlemania 9. Bottom line: creative choices. Like the one that had Hogan beating Yokozuna in seconds to close out the same event.

10 – Stone Cold vs. Hulk Hogan

The 2 biggest icons of the wrestling business were rarely at the same place, at the same time. And, when they were, something else was missing.

In WCW, both occupied the same time and space when Hogan came on board in 1994. However, Austin was in midcard purgatory and nowhere near the top of the food chain, where Hogan sat pretty.

However, once Austin reached peak popularity in 1998, they were separated by promotional lines.

At the time – or even in 2002 when the nWo invaded WWE – the match could have been a potential record-breaker.

Why It Didn’t Happen: One reason was creative choice. WWE had the option of putting Rock or Austin with Hogan. They went with Rock and the match was a success, its only sin that it denied fans of Austin vs. Hogan. Years later, in 2005, Hogan made a rare Raw appearance and teased a confrontation with Austin, but nothing came of it. Austin, besides being retired, repeatedly mentioned he didn’t see their styles meshing well (I agree Rock is a much better fit) and was afraid the match quality wouldn’t live up to the hype. Nothing came of it in 2002, or in 2005.

Can you think of another Wrestlemania match that woulda, shoulda, coulda?


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