Professional wrestling is all about the matchups. Some of the most exciting moments that have put fans on the edge of their seats are when two larger than life characters finally cross paths in the ring. Usually the competitors have been kept apart either via being in different promotions, coming up in different generations, being sidetracked by different feuds or just not being on the active roster at the same time.
These are considered “dream” matches and quite often these types of contests are highly unlikely to ever happen given various circumstances. However, history has delivered quite a number of them with satisfying results: Ultimate Warrior vs. Hulk Hogan, The Rock vs. Stone Cold Steve Austin, The Undertaker vs. Shawn Michaels are just a few that come to mind.
Often, though, dream matches fans were long craving for that actually came to fruition are delivered in such a way that they would’ve been better off being played out in the imaginations of fans rather than in real life.
With expectations being sky high, there have been match-ups between Superstars that fans had only fantasized about that were tremendously disappointing. There are various reasons a dream could turn into a dud. Sometimes the wrestlers are well past their prime when the match is finally booked. Other times it’s due to sloppy execution, contrasting styles or a lack of chemistry. Whatever the case may be, the overwhelming scenario led to underwhelming results.
Fantasy doesn’t always translate well in reality and this list of dream matches is proof that we should be careful what we wish for.
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29 The Rock vs CM Punk - Royal Rumble 2013
The Rock had finally come back to the WWE in 2012 and it wasn’t for a quick cameo or promo or even a one-off match but it was actually to compete as an active competitor and go for the gold. The Rock was slotted to go one-on-one against the longest reigning WWE Champion of the modern era in CM Punk. The buildup of the match was great and the trash talking promos between the two were even better.
Punk had a legitimate gripe against The Rock coming in as a part-timer and trying to take his Championship and matched up well on the mic, going counter-to-counter against The Rock’s verbal barbs. When the match finally went down at the Rumble in 2013, it failed to live up to the hype.
The Rock showed a lack of wrestling cardio and ring rust in the contest which showed and after interference from the Shield, a false finish and a match restart, it was a bit over-booked. Ultimately the Rock won quite predictably with a People’s Elbow which infuriated hardcore fans. Though it wasn’t a bad match by any means, it could not meet the overly high expectations placed on it.
27 Jeff Hardy vs Matt Hardy - WrestleMania XXV
Before the “Final Deletion” and the feuds the two Hardy brothers had on TNA Wrestling, the Hardys squared off against one another on the big stage at WrestleMania and it should have been a bigger deal than it was.
Matt and Jeff Hardy were the tag team of the new millennium and revolutionized tag team wrestling with their innovative offense and high-risks. When it came to potential and popularity, fans and wrestling experts pointed to Jeff Hardy as having the higher ceiling over his older brother. The jealousy and resentment Matt Hardy had due to those opinions made for a perfect story to tell as the two became bitter rivals leading to a match at WrestleMania 25.
When looking back at WrestleMania 25, most people only remember the epic Undertaker vs. Shawn Michaels contest and little else. Some even forget that Matt Hardy vs. Jeff Hardy is on that very same card which goes to show just how disappointing this match was. The Hardys had a chance to steal the show as they often did together as a team, but against each other they failed to do so.
25 Muhammad Ali vs Antonio Inoki
While Vince McMahon may have created WrestleMania years later as a revolutionary event where big-time wrestling spectacles would be showcased, his knack for making fantasy match-ups come to life took place long before WrestleMania’s inception. A prime example was the promotion of an infamous “Boxer vs. Wrestler” match that was gold on paper but a disaster in execution.
Boxing legend Muhammad Ali squared off against Japanese wrestling legend Antonio Inoki in 1976. Both were gigantic names in their respective sports so it captured the attention of many seeing these two legends go against eachother in a special attraction contest.
The initial plan was to have a worked match as agreed by the two men, but Ali and his management feared Inoki would flip the script and shoot on Ali with the intention of embarrassing the boxing great. As a result, the rules of the fight were changed, making it illegal for Inoki to grapple Ali, handicapping Inoki.
The fight would be a tentative bore that wasn’t a fight at all as both men stalled and rarely had an exchange. What potentially could have went down as an amazing cross-promotional bout if booked properly, was a snoozefest that ended in a draw.
23 Bret Hart vs Vince McMahon - WrestleMania XXVI
The Montreal Screwjob will go down as one of the biggest scandals in pro wrestling history and was the reason for nearly 13 years of real-life bad blood between Vince McMahon and Bret “The Hitman” Hart. During that span of time, many fans relished at the thought of Vince McMahon squaring off against the man he screwed in a match, and what better venue than in front of a WrestleMania crowd?
Vince McMahon had proven that he could deliver on a big stage at WrestleMania with memorable matches against Shawn Michaels, Hulk Hogan and his own son Shane on the biggest PPV of the year. When Bret Hart made a long-awaited comeback to WWE, it made all the sense in the world to turn this fantasy into reality at WrestleMania XXVI.
The problem here though was that McMahon was pushing 70 and Bret Hart was a 53 year old stroke victim. The match was a poorly executed and long, drawn-out disaster. Seeing Vince get his comeuppance wasn’t as satisfying as one would’ve thought and the match was universally panned.
21 Shawn Michaels vs Hulk Hogan - SummerSlam 2005
It was booked as the Icon vs. the Legend but what could have been a classic contest between two all-time greats ended up being muddied by backstage politics and execution that was largely influenced by egos clashing backstage.
Hulk Hogan made a return to the WWE in 2005 after a hiatus for some time and was teaming with the Heartbreak Kid in several tag matches until Michaels turned on the Hulkster. HBK would cut vile promos on Hogan and mock him which Hogan disapproved of. The egos would clash with Vince McMahon backstage when it came to the booking of their match and once HBK caught wind of Hogan wanting to do a one-off match where he’d be victorious rather than a series of matches with both getting wins, HBK took matters into his own hands.
At Summerslam, Hogan and HBK would face off and HBK would bounce around the ring overselling Hogan’s offense to the point of cartoony ridiculousness. The match has become infamous for Shawn Michaels theatrics overshadowing the contest rather than being an epic showdown.
19 Bray Wyatt vs Undertaker - WrestleMania 31
When Bray Wyatt stepped onto the scene in WWE he had the ominous entrance, the scary promos and the delivery in the ring that harkened back to the Undertaker. When Bray Wyatt began to claim himself as the new face of fear of the WWE, it solidified a fantasy of Bray Wyatt perhaps one day taking on The Undertaker at WrestleMania. Fans reveled with the idea of an epic contest between the two men and hopefully having Bray Wyatt take the Undertaker’s streak as a sort of torch passing to truly be the face of fear that the Undertaker had long been for the company.
This fantasy would come true but again, it was unfortunately not the way that it was originally hoped because of circumstances beyond the fans control. The Taker had lost his streak to Brock Lesnar and Bray Wyatt had lost a lot of momentum as a character, losing multiple high profile matches.
Bray Wyatt and Undertaker would go against each other at WrestleMania 31 and the Undertaker would win convincingly in a match that was underwhelming and unmemorable.
17 Rob Van Dam vs. Shawn Michaels - Monday Night RAW
Many fans would be surprised to note that Rob Van Dam and Shawn Michaels had actually faced each other one on one before—in a WWE World Heavyweight Championship match. Rob Van Dam was the popular franchise player in ECW and possessed an innovative and dazzling offense which made him a household name. Fans drooled at the thought of RVD competing on a larger stage against the likes of an equally talented and athletic Shawn Michaels and considered that a fantasy match worthy of a WrestleMania main event.
When RVD made the jump to WWE, this dream match actually took place on an episode of RAW in 2002 and unfortunately it is largely forgotten about due to the booking. RVD and Shawn’s chemistry wasn’t the greatest as both had to take a bit of time to feel eachother out. While it was fun to see both men in the ring together, the match didn’t kick into the expected high gear that HBK and RVD thrive in. Another reason why the match is disappointing was the unresolved ending because Triple H interfered to attack both men. Sadly, there was never a rematch between the two to see who would come out on top over the other.
15 Bret Hart vs HBK - WrestleMania XII
While Shawn Michaels and Bret Hart had faced off against each other before, it was not as high profile of an atmosphere as it was at WrestleMania 12 when both men competed in the main event for the WWE Championship in a 60 minute Iron Man Match.
Hart and Michaels were the faces of the new generation in WWE who were shifting away from the stars of yesteryear in Hulk Hogan and Randy Savage and investing in the Hitman and the Heartbreak Kid. Bret Hart solidified himself as a solid World Champion while Michaels climbed steadily up the ranks as a fan favorite. When the match was announced, fans marveled at the possibilities of seeing Shawn and Bret tear then house down for an hour.
While the match wasn’t necessarily terrible by any means, it was an Iron Man match that did not have a single pinfall or submission during the first 60 minutes making it lose a lot of momentum when it came to drama. A sudden death overtime was implemented and Shawn Michaels won within minutes of it to capture his first World championship. Considering the 5 star matches both of these men could easily perform, it’s quite deflating they had a match that is considered boring by many wrestling fans because of how it was booked.
13 Hulk Hogan vs Ric Flair - Monday Night RAW 2002
It’s quite astounding that Hulk Hogan who was the franchise player of the WWE in the 80s and early 90s versus the franchise player of the NWA/WCW in the 90s and early 90s never took place on a big stage until both men were well past their primes.
When Ric Flair was signed to the WWE in 1991, he brought along with him the NWA/WCW championship and it almost seemed inevitable that he would get in the ring with Hulk Hogan for an epic showdown. This certainly was going to be the case at WrestleMania VIII in 1992 but after testing the match a few times off of television, it was reported that the matches were subpar so the match was scrapped.
After a few underwhelming contests in WCW, Ric Flair vs. Hulk Hogan finally did happen on an episode of RAW in 2002 for the WWE Championship yet it ended in disappointing fashion via DQ featuring a ton of interference from the NWO and Stone Cold Steve Austin.
11 Scott Hall vs. Stone Cold Steve Austin - WrestleMania X8
Another match of the early 2000’s no one ever would have conceived happening was Stone Cold Steve Austin squaring off against NWO original Scott Hall on the WrestleMania stage. Hall and Austin were largely apart from each other during the height of their popularity with Hall leaving WWE to join WCW right when Stone Cold was about to skyrocket in WWE.
When the NWO came to WWE in 2002, they waged war against the faces of the company in Austin and The Rock. At Wrestlemania X8, The Rock would face Hollywood Hogan and Stone Cold would be matched up with Hall. Austin was very disappointed he wasn’t facing Hogan in the headlining match and his frustration showed in this contest. Both men didn’t seem to click well that night and while Austin won, the match was clearly overshadowed by the greatness that was Rock vs. Hogan later that night.
9 Brock Lesnar vs Goldberg - WrestleMania XX
On paper, this matchup made wrestling fans salivate at the thought of seeing these two monsters tear into each other, but in execution it was anything but epic. Goldberg was the crowned jewel of WCW in its final years. His long undefeated streak and his short intense matches made him look like a god amongst men. The same could be said of Brock Lesnar in WWE and he was often compared to Goldberg because of the dominating fashion in which he would destroy his opponents.
With both of these men on the roster at the same time, it would have been foolish for WWE to not pit the two behemoths together on the grandest stage of them all at WrestleMania XX. That’s exactly what WWE did and to add even more sizzle to the steak, they added Stone Cold Steve Austin as the special referee.
However this was a recipe for disaster due to the internet leaking that both Goldberg and Lesnar were leaving WWE after the show. The crowd let their displeasure be known from their discovery by booing and heckling both men mercilessly which overshadowed the match and affected both men's performance. The match was terribly executed and ended with Goldberg winning in ten forgettable minutes. The only saving grace was Stone Cold delivering stunners to both men to the delight of the crowd as a sort of “good riddance” to both men.
7 Hulk Hogan vs Ultimate Warrior 2 - Halloween Havoc
As mentioned in the intro, The Ultimate Warrior vs. Hulk Hogan main event of Wrestlemania VI in 1990 was a fantasy matchup that far exceeded expectations. Hulk Hogan was the heroic face of the company who was firmly established. Warrior was rising quickly in popularity with his intense energy, colorful look and bizarrely inspirational promos. The match was built up impeccably and the execution was even better. Warrior came out on top and there never was a rematch—until 1998 that is.
In WCW, Hollywood Hogan was on top of the world as the leader of the NWO and also had creative control over his character. Using his clout, he was able to get WCW to lure Warrior out of retirement to rekindle a feud with the hook being that Hogan had beaten them all, except Warrior. The buildup was weird and confusing and the match itself, which took place at Halloween Havoc, was a convoluted mess that even had a botched ending. It was a tale of two legends past their prime trying to reignite the glory days and it fell tremendously flat. This is one match wrestling fans definitely wish could be stricken from the history books.
5 Sting vs Hulk Hogan - Starrcade '97
In what was classically seen as a case of perfect build up with a mediocre match, Sting finally getting his hands on Hulk Hogan on the biggest WCW PPV of the year should’ve meant so much more.
Hogan and Sting had both gone through transformations in 1996. Both were the bright colored good guys of the 90s but when Hogan moved to the dark side and formed the NWO with Scott Hall and Kevin Nash, he changed the entire landscape of the wrestling industry. The faction took apart the WCW and dominated the promotion while Sting drifted off and watched the destruction unfold from the rafters. With WCW aching for a hero, Sting would finally be a spectator no longer and would begin targeting the NWO. Fans were frothing at the mouth wanting to see Sting finally take down the evil Hogan once and for all.
It was supposed to be a storybook ending to a long roller coaster feud but Sting—the last beacon of hope for WCW— defeating the mastermind of the NWO left fans deflated. Fans were treated to a one-sided affair as Hollywood Hogan beat down Sting and then gained a pinfall over him –which was supposed to be booked as a fast count. Bret Hart would run down to restart the match as referee and Sting would win with the Scorpion Deathlock. The botched pin, the false finish and the overbooking took fans out of the moment and may have been the moment the red-hot NWO vs. WCW storyline jumped the shark.
3 Bret Hart/Hogan vs Sting/Warrior
This stacked tag match is eye-popping when you consider the star power involved, but it has since been largely forgotten about because of the constantly shifting atmosphere of the Monday Night Wars. RAW and Nitro were going tit for tat to grab ratings and viewers in 1998 with high profile PPV worthy matches being given away on free TV and this was one of those dream contests that fans never would’ve thought would happen.
Bret Hart and Hulk Hogan, who for most of their careers never crossed paths were tagging up for the first time ever. Their opponents were Sting and the Ultimate Warrior, who came up in the wrestling business together as the Blade Runners but then took separate paths—Sting being a mainstay of WCW and Warrior becoming a household name in WWE—and after over a decade apart were teaming up again.
The match involved a lot of stalling and bizarrely Warrior wasn’t in wrestling gear and never took his entrance coat off. In the end, the match was thrown out via NWO interference mere minutes into the match which is likely why it was so disappointingly forgettable.
1 The Entire WCW vs WWE InVasion
Oh, what could’ve been with the InVasion angle of 2001. A WCW vs. WWE showdown PPV was something wrestling fans long fantasized in their minds, especially during the peak of the Monday Night Wars. The idea of both promotions bringing their best to match-up against one another and see which promotion would reign supreme was something infeasible at the time, which made it all the more alluring.
When WCW was purchased by WWE and Shane McMahon became the “owner” in storylines and “merged” with ECW, this dream looked to be finally coming true to the delight of wrestling fans everywhere. However, it wasn’t in the fashion fans envisioned. Because of contractual disputes, the premium talent of WCW didn’t sign to WWE, making the WCW side very thin in terms of competition. There was no Sting, no Hall and Nash, no Goldberg, no Flair and no Hogan.
With a weak WCW lineup to work with, the WWE scrambled to keep things interesting by turning Stone Cold Steve Austin heel and having him join WCW which was a terrible idea in hindsight. In the end, the WWE would vanquish WCW. As predictable as it was, it’s still a shame that WCW wasn’t as stacked as it could have been for the Invasion to really be a dream come true for die-hard fans.
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