Over the years, there have been some incredible dream matches that have taken place inWWEand beyond, allowing the fans to finally see their favorite competitors in the ring grapple. From Ric Flair finally scrapping with Hulk Hogan, to AJ Styles connecting with John Cena, wrestling fans have experienced some of the best matches of their generation simply bybeing patient and waiting for the moment to arrive.
Some of these dream matches, however, for a multitude of reasons, will never grace the television screens of wrestling fans, andthe encounters will play out in the theater of the mind forever.These ten matches are among the greatest showdowns that never happened, and ones wrestling fans wish they could have seen.
10DDP vs. The Rock
People’s Champion vs. People’s Champion
One of the easiest matches that felt like a slam dunk post-Invasion in WWE was Diamond Dallas Page vs. The Rock,a story based on who was truly the People’s Champion.Both men, gaining support from the crowds and getting over with the fans by being themselves, each representing their brands as the ambassadors of the people in WWE and WCW, seemed like it would have made for an easy story to tell.
The stars never aligned for these two, and when DDP joined WWE in 2001, he was brought in with a clunky and awkward gimmick: the stalker of Undertaker’s wife.This angle didn’t resonate with fans the way it may have been intended, and although DDP held the European and Tag Team Championships with WWE, DDP’s opportunity to capture the People’s Champion moniker from The Rock never came to pass, and fans missed out on what could have been an incredible showdown.
9CM Punk vs. Steve Austin
Trash Talkers At Their Finest
Steve Austin will forever be one of the greatest trash-talkers of all time in professional wrestling, and although there could be a case for many to be made,no one comes quite as close to the Rattlesnake in terms of trash-talking as CM Punk.In a setup starting in 2011, and continuing through a contentious interview ahead of WWE 2K13, it seemed like everything was full steam ahead for this feud, and set up for one last Austin run.
Those dreams were dashed whenCM Punk was fired from WWE in 2014because of acrimonious circumstances and didn’t return to the company until 2023, while Steve Austin had what appears to be his final match with Kevin Owens atWrestleMania38. While Punk has returned to WWE, it seems unlikely now that the Rattlesnake and The Best in the World will tussle up in the ring.
8Gunther vs. Brock Lesnar
Two Giants Clashing
When Brock Lesnar vs. Bobby Lashley finally took place, two modern gladiators still at the top of their game clashing for the industry’s biggest prize, fans turned their attention to another big man facing off, this time with Gunther as Lesnar’s chosen foe. Both men, heavy in stature and heavier in fist,seemed destined for a collision course in the wake of their 2023 Royal Rumble stare-down,especially after Gunther referred to Lesnar as his “end boss”.
Legitimate issues would tamp down any chance of this match happening for the foreseeable future, as Lesnar was named in Janel Grant’s lawsuit against Vince McMahon and WWE and subsequently pulled from all WWE programming and storylines. Due to the nature of the allegations,it’s unclear at this time whether we’ll ever see Lesnar return to WWE, so this match lives in the minds of wrestling fans everywhere as a major “what if” moment.
7Dean Malenko vs. Penta
Cruiserweight Lucha Glory
In the WCW Cruiserweight division, there may have been no one better thanDean Malenko, a true master of his craft and worker extraordinaire who, along with a young Rey Mysterio, Eddie Guerrero, Psychosis, and La Parka, was an integral and exciting part of the Monday Night Wars era by giving fans something fresh each week. It’s with this in mind thatthe best modern opponent for Malenko would be Penta,WWE’s newest and most exciting Lucha Superstarwho’s already left his mark on the WWE ring with that Cruiserweight feel.
Both men exist and wrestle in different timelines, and there’s regrettably no reality that this face-off would ever take place. However,it’s a fun exercise to think about their dynamics in the ringand what kind of match these two performers would put on, especially having such similar styles and approaches.
6The Fiend vs. The Demon
Dark Powers Could Have United
Bray Wyatt’s alter ego, The Fiend,stormed onto the WWE scene with venom and fire in 2019, laying waste to everything in its path, including Finn Balor, his first proper opponent after the character’s debut. Laying in wait was Balor’s dark incarnation, The Demon, who brought an equal amount of darkness to the squared circle, and a dark story based on these characters could have allowed for a cool, supernatural face-off.
For whatever reason, or no reason,the two incarnations never faced off. The Fiend, fresh off a handful of creative missteps with the character followed by his release in 2021, was not featured again on WWE programming after Wyatt returned to the company in 2022.Although Wyatt had been preparing to revive The Fiend, no plans ever came to fruition due to his untimely passing in 2023.
5Brothers of Destruction vs. The Outsiders
Top Big Man Tag Teams From The Attitude Era
Another match that felt like a slam dunk post-Monday Night Wars: the two stalwarts of WWE, The Undertaker and Kane, facing off against the returning WCW defectors, Scott Hall and Kevin Nash, to prove who was the more dominant force in professional wrestling.Four big men, among the most dominant of their eras, would have made for some impressive storylines and television.
In the wake of the Monday Night Wars' end,Hall and Nash did not immediately come back to WWE, as their WCW contracts were guaranteed through the end of 2001,and when they returned, they were immediately thrown intoa revived version of the original nWowith Hulk Hogan. With Nash’s injuries and Hall’s release lying in wait, there was no time to properly build this angle to its potential, and wrestling fans were not given a chance to see who would reign supreme in this showdown.
4Hulk Hogan vs. Steve Austin
An Obvious Showdown and a Massive Miss
Arguably two of the biggest names in wrestling are Hulk Hogan and Steve Austin, and when Hogan signed with WWE again in 2002, the wrestling world immediately set its eyes on this epic showdown -The Rattlesnake vs. “Hollywood” Hogan. It seemed like the path of least resistance for an incredible story, especially as Hogan was flanked by nWo stablemates Kevin Nash and Scott Hall, and the perfect capstone to the Monday Night Wars.
Hogan was paired off with The Rock, andAustin, who admitted he was not in the best shape physically due to his extensive injuries, worked a lackluster program with Hall, both of which culminated atWrestleMania X8. The only actual showdown we’ll ever see between Hogan and Austin was during the 3-on-2 handicap match involving Austin, Rock, and the nWo from the July 22, 2025 episode ofMonday Night Raw, which saw the two face off for a meager 24 seconds.
3The Briscoes vs. The Dudley Boyz
Two of the Greatest Tag Teams Of All Time
Considered one of the greatest tag teams of all time,Jay and Mark Briscoe never competed in a WWE ring,but there were other opportunities for them to square off with some of the best tag teams outside a WWE ring. One of these teams was The Dudley Boyz, one of the most decorated tag teams in wrestling history, and this match could have been one for the ages.
Unfortunately, the opportunity never presented itself, as both teams had expressed interest in facing off against one another,with D-Von Dudley calling the missed opportunity"one of my biggest regrets.“The tragic passing of Jay Briscoe in 2023 ended any opportunity for these two titan teams to face off, forever leaving a mystery to who would be the greatest tag team of all time.
2Bret Hart vs. Daniel Bryan
This Would Have Been A Technical Masterpiece
One of the greatest workers of his time or any time, Bret Hart truly is the best there is, the best there was, and the best that ever will be. This generation’s Bret Hart, Daniel Bryan, exuded many of the same technical gifts and strengths as Hart possessed, andevery “what if” scenario in professional wrestling features a face-off between these two in almost every capacity.
Another victim of different timelines, Hart and Bryan competed in two different worlds and two different eras, rendering a match with both of them together in their primes impossible. A match that would have ranked among the highest and most well-received matches in history, the theater of the mind is where this match stays.
1Sting vs. The Undertaker
Seriously, How Did This Not Happen?
The “what if” of all “what ifs” in professional wrestling, Sting vs. The Undertaker is a long-fabled, and often discussed, dream match among professional wrestling fans.The darkest characters from WCW and WWE,the two blazed a similar path through the supernatural elements of storytelling and were at the top of their promotions in almost parallel time.
Multiple explanations have come forth as to why this never took place,with the current prevailing narrative being that one party simply just wasn’t interested in seeing this match happen. Whatever the case, this showdown will be debated for decades to come as to who is truly the best: The Icon or The Phenom.
