Ranking the greatest matches in Wrestlemania history
March 30, 2020
From Hulk Hogan’s groundshaking body slam to Seth Rollins’ infamous Money in the Bank cash-in, iconic moments and legendary contests helped morph Wrestlemania into the must-see, nostalgia-driven spectacle it is today.
Compiling a subjective listing of the greatest matches in Wrestlemania history was quite a trying task. A number of great contests failed to crack the top 15, which is more a testament to the depth and magnitude of Wrestlemania than an indictment on the omitted performances.
Hopefully, this list allows readers to revisit their fondest childhood memories while also celebrating the moments that had viewers glued to the edge of their seats during their formative years.
Let’s take a look back on the greatest matches in Wrestlemania history.
Just Missed The Cut
26. Kurt Angle vs Brock Lesnar (Wrestlemania XIX)
25. CM Punk vs. The Undertaker (Wrestlemania XXIX)
24. Shawn Michaels vs Chris Jericho (Wrestlemania XIX)
23. Edge vs Mick Foley; Hardcore Match (Wrestlemania XXII)
22. Shawn Michaels vs Ric Flair; Retirement Match (Wrestlemania XXIV)
22. Triple Threat Ladder Match; WWF Tag Team Championship (Wrestlemania 2000): Hindsight allows us to view the Triple Threat Match between Edge & Christian, the Hardy Boyz and the Dudley Boyz as a precursor to their legendary series of Tables, Ladders and Chairs contests. Nevertheless, the pure innovation and recklessness featured in this particular contest warrants recognition in the Honorable Mentions column.
21. Ric Flair Vs. Randy Savage; WWF Championship (Wrestlemania VIII): Though admittedly dampened by an anticlimactic finish and a bit of overbooking during the latter portion of the contest, the match that should have headlined Wrestlemania VIII benefitted from an enthusiastic crowd, an engrossing backstory and excellent heeling from both Flair and ally Mr. Perfect. By the time “The Macho Man” Randy Savage commenced his valiant comeback, the crowd was salivating at the prospect of a title change.
20. Money In The Bank Ladder Match (Wrestlemania XXI): Five of the six competitors in this contest were either future or former World Champions, with the lone exception being Shelton Benjamin, who entered as Intercontinental Champion. This match benefitted from its innovative concept, flawless execution and high level of athleticism displayed by the participants, with each man contributing to the bout’s entertainment factor.
19. Hulk Hogan vs The Rock (Wrestlemania X-8): Anticipation for this match was so high that the subtlest of moments sent the crowd into an unadulterated frenzy. Though the pace left quite a bit to be desired, never before in the history of the industry had two icons of vastly different eras battled in such a high-stakes affair. From the infamous Rock-Hogan staredown to the final result, these two titans proved that their status within the industry superseded the traditional heel/babyface dynamic, with each man receiving an ample amount of respect and adoration before, during and after the contest.
18. Edge vs. Undertaker; World Heavyweight Championship (Wrestlemania XXIV): Edge delivered some of the best heel work of his career in the build-up to this match, casting the Undertaker’s undefeated streak in doubt at a time when it appeared unbreakable. Insinuating that he had each of the Undertaker’s tendencies expertly scouted, Edge was presented as the perfect foil to the mystique of the Undertaker, despite being relatively diminutive in stature next to “The Deadman.” The match also featured a nice rhythm, benefitting from a surplus of seamless counters and a topsy-turvy trajectory to keep fan interest at its zenith.
17. Daniel Bryan vs. Batista vs. Randy Orton; WWE Championship (Wrestlemania XXX): As stated earlier, this match not cracking the top 15 is more a testament to the contests listed above it than an indictment on the efforts put forth by these three men. Prior to the contest, the WWE Universe proved itself willing to go to any lengths necessary to ensure that fan-favorite Daniel Bryan received the opportunity that he so richly deserved. After being put through the proverbial wringer, fans saw their appetites satiated as Bryan — who had previously defeated Triple H in a fantastic qualifying contest to open the show — forced Batista to submit to his Yes Lock submission maneuver, capturing the ever-elusive WWE World Heavyweight Championship and sending WWE’s impassioned fans into near delirium.
While this match hasn’t aged as well as some of the others on our list, its historical significance can’t be understated as it marked the culmination of Bryan’s ascent from real-life and kayfabe “B+” player to legitimate main event talent.
16. Brock Lesnar vs. Roman Reigns vs. Seth Rollins; WWE Championship (Wrestlemania 31): Rollins’ unprecedented Money in the Bank cash-in salvaged a match laboring through fan apathy. By the time Reigns challenged Lesnar for this WWE Title, fans grew impatient with Reigns’ seemingly indefinite pursuit of the WWE Championship. Furthermore, as a part-time performer, Lesnar was wholly unlikable, the absent champion depriving the next generation of their moment in the sun.
As Rollins sprinted to the ring, the audience’s collective sigh of relief conceded to rapturous enthusiasm. For a brief moment, Rollins’ inclusion appeared to be an instrument to protect both challenger and champion from a pinfall defeat. When Rollins stomped Reigns face into the mat to claim his first WWE Championship, it represented a crowning moment since immortalized in Wrestlemania history.
15. Bret Hart vs Shawn Michaels: Iron Man Match for WWF Championship (Wrestlemania XII)
Match Background: After a tumultuous 1995 that saw Shawn Michaels tarnish his reputation with both kayfabe and real-life setbacks — Michaels failed to win the WWF Championship at the previous year’s Wrestlemania, was assaulted and suspended for a fight involving a U.S. Marine, forfeited his Intercontinental Championship and suffered a kayfabe concussion at the hands of Owen Hart — 1996 was set up to be a vindictive year for the transcendent superstar. As the 18th entrant in the 1996 Royal Rumble, Michaels overcame staggering odds to win his second consecutive Royal Rumble, last eliminating Diesel in a match that can be accurately described as “the land of the giants.” Bret Hart would fuel the redemption narrative by outlining each of Michaels’ shortcomings, claiming that he wanted to plant the final seed of doubt within Michaels’ mind. After defending his Wrestlemania main event berth at In Your House 6 against a bitter Owen Hart, the stage was set for champion Bret Hart to square off against Michaels in an Iron Man Contest for the WWF Championship.
What Made The Match Great: After years of relying on over-the-top gimmickry and formidable physiques to headline their grandest pay-per-view, WWE opted to hand the reins to their two top performers in the most physically demanding Iron Man Match, much to the appreciation of its fan base. Fans who followed the career trajectories of the two participants noted how similar their paths had been up to that point, as each man ascended through the tag team ranks, excelled in the midcard and earned their place among the elite despite their less-than-ideal size (relative to Vince McMahon’s standards). Though a bit long, the match itself was a technical masterpiece, providing the in-ring apex of one of the greatest personal and professional rivalries in WWE history. Furthermore, the conclusion was one of the more brilliant finishes this writer has ever seen.
Result and Aftermath: Hart, on the verge of victory, locked Michaels in a deep Sharpshooter during the waning moments of the contest. However, despite maintaining complete control during the dying embers of the bout, Hart was unable to force the “Heartbreak Kid” to submit before time expired, ending the match in what many perceived to be a draw. Out came WWF President Gorilla Monsoon, demanding a winner be declared and initiating a sudden death rules overtime period. Approximately one-and-a-half minutes into the overtime period, Michaels landed consecutive Sweet Chin Musics flush on Hart’s chin, incapacitating his opponent and earning the “Heartbreak Kid” his first WWF Championship.
Michaels would hold onto the WWF Championship until November of that year, feuding with the likes of Diesel and the British Bulldog before dropping the title to Sycho Sid at Survivor Series 1996. However, this contest will always be remembered as the launching pad that helped propel Shawn Michaels’ storied legacy to new, unforeseen heights.
14. Hulk Hogan vs. Andre the Giant (Wrestlemania III)
Match Background: Prior to the buildup to Wrestlemania III, Andre the Giant and Hulk Hogan were presented as allies, even claiming to be best of friends. During an edition of Piper’s Pit in January of 1987, Hulk Hogan received recognition for his remarkable accomplishments, finding himself the recipient of a trophy for his three-year reign as WWF Champion, to which Andre the Giant came out to congratulate his friend.
The following week, also on Piper’s Pit, Andre the Giant received a much smaller trophy for an undefeated streak which spanned 15 years, to which Hogan returned the congratulatory message.
However, rather than fading into the background of the segment, Hogan found himself the focal point of Piper’s follow up interview, much to the annoyance of Andre the Giant, who responded by walking out of his own ceremony. Bobby Heenan, who had long been recruiting talent in an effort to thwart Hulkamania, revealed himself to have taken up managerial duties for Andre, challenging Hogan for his championship and claiming Hogan only befriended Andre to avoid defending his championship against the undefeated superstar. After Hogan refused to accept Heenan’s taunts, Andre proceeded to rip Hogan’s shirt from his body and tore his crucifix from around his neck, detonating their relationship.
What Made The Match Great: The drama, the suspense, the participation and the “moment.” Make no bones about it, this match was not technically sound or particularly entertaining from an in-ring perspective. In fact, outside of the pre-match staredown and Hogan’s iconic bodyslam on Andre, hindsight exposes this match as for plodding, slow and very heavily reliant on strikes.
By the time this dream match took place, Andre was far past his in-ring prime, suffering from the same health issues that eventually contributed to his death. However, while the remaining matches on the list warrant inclusion through precise in-ring execution and excellent storytelling, this match is celebrated for solidifying Wrestlemania as the must-see spectacle it has become today.
Nevertheless, we’d be remiss if we didn’t admit that watching this match 28 years after it took place won’t provide much excitement from a pure in-ring standpoint.
Result and Aftermath: After the infamous bodyslam that grounded Andre the Giant, Hogan executed his patented Leg Drop to earn the three count and retain his WWF championship. The two men would have a rematch at “The Main Event ” on NBC on Feb.5, 1988, a match which drew a record 33 million viewers. Andre the Giant would proceed to end Hogan’s four-year reign as champion thanks to a perceived screwjob orchestrated by referees Dave and Earl Hebner. The feud would culminate at Wrestlemania IV during the tournament to crown a new WWF Champion, though both men were disqualified after using a steel chair, an underwhelming conclusion to a rivalry that helped shape the landscape of the WWE.
13. Randy Savage vs. The Ultimate Warrior; Retirement Match (Wrestlemania VII)
Match Background: During the latter half of 1990, Randy Savage exhibited an unyielding desire to regain the WWF Championship he lost at Wrestlemania V. Savage repeatedly prodded then-champion the Ultimate Warrior for a title shot, But Warrior continuously refused, classifying Savage as “unworthy.” To the outrage of “The Macho Man,” the number one contendership went to Sgt. Slaughter instead, provoking Savage to take matters into his own hands. At the 1991 Royal Rumble, Savage and valet Sensational Sherry interfered during Warrior’s championship contest against Sgt. Slaughter, striking the champion with a scepter and costing the Ultimate Warrior his WWF Championship. Over the next few weeks, the feud rapidly escalated before boiling over when the Ultimate Warrior challenged Savage to a retirement match at Wrestlemania VII.
What Made The Match Great: For its time, the match was spectacular, though if you watch it today, you may quickly find yourself disenchanted by the dated in-ring mannerisms and awful theatrics employed by the Ultimate Warrior. However, what this match is best remembered for is the emotion elicited by its conclusion.
Though the retirement stipulation has since become diluted and–depending on the circumstance–telegraphs predictability, the stakes were high back in 1990, adding an iconic feel that was difficult to capture in that era. The match itself was very entertaining, seeing Savage carry the Ultimate Warrior to the best match of the latter’s career. Additionally, despite his status as a heel, fans sympathized with Savage’s vulnerability as his contributions were already recognized as some of the greatest to ever grace the industry. However, what truly memorialized this match in the minds and hearts of fans was its role as the culmination of the greatest love story in WWE history.
After losing the WWF Championship to Hogan at Wrestlemania V, Savage would rebound by winning the King of the Ring tournament and dumping the services of his valet (and real-life wife) Miss Elizabeth in favor of “Sensational” Sherri Martel. After suffering defeat following consecutive leaping shoulder blocks, Savage lay dejected and alone in the middle of the ring as “Sensational” Sherri looked on in disgust. However, rather than supporting her client, Sherri opted to viciously assault a vulnerable Savage with kicks and strikes, prompting Elizabeth, who had been sporadically shown throughout the match as an onlooker, to jump the barricade and make her way to the ring. Elizabeth proceeded to grab Sherri by the hair and deposit her through the middle ropes before attempting to help the battered Savage to his feet, only to have her attempts swatted away by a panicked and disoriented Macho Man.
Tears streaming from her eyes, Elizabeth allowed Savage to regain his bearings. Initially, he had wrongly identified her as his attacker, eyeing her questioningly before spotting Sherri outside the ring screaming at him with fury and malice. After realizing Elizabeth had come to his aid rather than harming him, Savage embraced Elizabeth and raised her atop his shoulder, much to the delight of the openly weeping attendees and viewers at home.
Result and Aftermath: Following consecutive flying shoulder blocks, The Ultimate Warrior defeated Randy Savage via pinfall, forcing his retirement. However, Savage soon returned to the WWF as a color commentator, “marrying” Miss Elizabeth on-air at Summerslam 1991. By the following year, Savage returned as an in-ring performer, competing against Ric Flair for the WWF Championship at Wrestlemania VIII.
12. Owen Hart vs Bret Hart (Wrestlemania X)
Match Background: The feud between Owen and Bret Hart began at Survivor Series 1993, when Bret Hart, hobbled from a sustained injury, caused Owen to lose his balance and focus, subsequently contributing to Owen’s elimination from the match. A confrontation ensued, seeing Owen persistently demand a match with Bret before their reconciliation prior to the 1994 Royal Rumble. However, a similar scenario unfolded, as another Bret injury caused the referee to award the match to the Quebecers, provoking Owen to attack his brother in a fit of rage.
What Made The Match Great: Universally regarded as the greatest opening contest in Wrestlemania history, the Hart Brothers treated us to a display of both excellent chemistry and technical prowess. Each wrestler showcased an array of technical and stiff maneuvers, complemented by Owen’s expert heel tactics, which involved him celebrating each small accomplishment as if he had just won a presidential election. Additionally, the feud began via one of the great, relatable themes: jealousy toward a figure unfairly perceived as superior. However, to the pleasant surprise of many, Owen received his moment of triumph after countering Bret’s roll-up attempt into an inescapable pinning predicament of his own, earning a long-overdue victory over his elder sibling.
Result and Aftermath: Owen pinned Bret after countering a sunset roll-up into a pin of his own. After Bret’s victory over Yokozuna for the WWF Championship in the main event of Wrestlemania X, Owen and Bret continued their feud for the remainder of the year, seeing their immediate family’s allegiance divided between the two. Owen Hart further solidified his credibility by earning the honor of 1994 King of the Ring, but found himself unable to dethrone his brother as WWF Champion in a Steel Cage Match at Summerslam. The rivalry would come full circle at Survivor Series 1994, when Bret Hart, embroiled in a championship submission contest against Bob Backlund, found himself trapped in the Crossface Chickenwing. Owen Hart, feigning concern for his brother, coerced their mother into throwing the towel on Bret’s behalf, costing him both the match and his Heavyweight Championship.
11. Shawn Michaels vs. Razor Ramon; Intercontinental Championship Ladder Match (Wrestlemania X)
Match Background: After finding himself in a troubling predicament with the WWE front office, then-WWE Intercontinental Champion Shawn Michaels would be forced to vacate his title under storyline citation for violating the championship “30 Day Policy,” which states that without a proper title defense within a 30-day time frame, he would no longer be recognized as the official champion. With a vacant title on its hands, WWE announced a battle royale would take place to determine the two competitors that would face off in an Intercontinental Championship match. The two final competitors of the battle royale, Rick Martel and Razor Ramon would compete at the Sept. 27, 1993, Monday Night Raw for the vacant championship, where after an impressive Razor’s Edge, Razor Ramon was crowned champion.
However, while Razor Ramon was recognized as the official champion, Shawn Michaels returned from his real-life suspension claiming that since he had never actually been defeated for the Intercontinental Championship, he remained the rightful champion. Both men began to carry two indistinguishable title belts, each staking their claim as Intercontinental Champion. It was decided that the two champions would settle their dispute at Wrestlemania X in the second-ever WWE ladder match (the first being contested between Hart and Michaels in a forgettable match at Wrestling Challenge).
What Made The Match Great: Who can forget the iconic image of Michaels’ body splash onto Razor Ramon from atop the ladder? Second, innovation engraved this contest in the hearts of fans, as it was the first ladder match to be featured on a pay-per-view card. Fans quite literally had no idea where to set their expectations for such a contest, allowing each spot to be received with awe. An inspired Michaels and Razor Ramon put on one of the greatest performances of their storied, Hall Of Fame careers, and though Razor Ramon was credited with the victory, each man solidified his place among the upper echelon of WWE superstars.
Result and Aftermath: After Shawn Michaels found his right foot bound between the two top ropes, Razor Ramon was able to ascend the ladder unobstructed to retrieve the two Intercontinental Championship belts. A couple of weeks after the infamous contest, Razor Ramon would lose his Intercontinental Championship to Diesel on the April 13th edition of WWF Superstars with assistance from Michaels. The victory would spearhead a major push for Diesel, which saw him obtain the WWF Triple Crown within a calendar year.
10. Ricky Steamboat vs Randy Savage; Intercontinental Championship (Wrestlemania III)
Match Background: The blood feud between Randy Savage and Ricky Steamboat commenced when Savage viciously attacked Steamboat, delivering an emphatic elbow that forced Steamboat’s throat into the guardrail. Savage then ascended to the top rope before driving the ring bell into Steamboat’s throat, kayfabe (or storyline) crushing his larynx. Six months later, their heated feud culminated at Wrestlemania III, with Steamboat looking to strip Savage of the Intercontinental Championship.
A subplot to the match: George “The Animal” Steele accompanied Steamboat to the ring after developing an unsettling crush on Savage’s valet, Miss Elizabeth.
What Made The Match Great: If one were to study professional wrestling content from the late 1980s and early 1990s, you would find yourself increasingly disenchanted with the painstakingly slow pace of the era. However, deviating away from the era’s norm, Steamboat and Savage delivered a contest that, even by today’s standards, was both brilliantly executed and fast-paced, incorporating an impressive blend of high-flying action and ground attacks to win over their audience.
Furthermore, in an era defined by cartoonish gimmicks and outlandish promos, it was refreshing to see a simplified feud that centered around nothing more than a seething hatred between two competitors and a championship belt.
However, outside of providing an exhilarating contest that left fans breathless, this bout is recognized for inspiring future generations. Former WWE and AEW Champion Chris Jericho cites this contest as the standard that future WWE superstars strive to not only replicate.
Result and Aftermath: Ricky Steamboat countered an attempted bodyslam into a Schoolboy Rollup, earning both the three count and the Intercontinental Championship. Savage would continue to challenge Steamboat for the Intercontinental Championship at ensuing house shows, only to see his quest for redemption repeatedly fall short.
Steamboat would lose his IC Championship to the Honky Tonk Man on the June 3 edition of Superstars as real-life punishment for requesting time off to spend with his heavily-pregnant wife, who was expected to deliver the couple’s first child at any moment.
9. Triple H vs. The Undertaker; Hell In A Cell Match (Wrestlemania XVIII)
Match Background: After a ten-month hiatus following their brutal encounter at the previous year’s Wrestlemania, Undertaker resurfaced with the intent of challenging Triple H to a rematch. Enamored by the legacy of The Undertaker’s Wrestlemania winning streak, Triple H refused, claiming that preserving the streak was in the WWE’s best interest. Undertaker then taunted Triple H into accepting his proposal by comparing Triple H’s career to that of Shawn Michaels, whom The Undertaker defeated multiple times in high-profile contests. Triple H accepted the challenge, with Shawn Michaels volunteering to serve as special guest referee for the contest.
What Made The Match Great: Though billed the “End of an Era”, this match wouldn’t be the final match for either the Undertaker or Triple H. However, this match offered nostalgia, intrigue, brilliant in-ring execution and storytelling all within one 30-minute window.
Both men expertly teased the end of “The Streak,” introducing the idea of an overconfident Triple H from his real-life best friend Shawn Michaels (whom the Undertaker had repeatedly belittled in the build-up to the contest) serve as the special guest referee. As if that wasn’t sufficient cause for apprehension, the three performers left fans clutching at straws whenThe Undertaker suffered a Sweet Chin Music transitioned into a Pedigree, only to kick out at what unofficially must be considered a two-and-three-quarters count. This match also featured brutality (both competitors mercilessly used a sledgehammer on one another), scarcely rivaled star power and an inordinate amount of jaw-dropping suspense. Following the contest, the post-match embrace between three of the most celebrated superstars of WWE’s most successful era was an iconic moment in itself. Simply put, it is impossible not to tip your cap to this performance.
Result and Aftermath: The Undertaker defeated Triple H via pinfall after leveling Triple H with a sledgehammer and a Tombstone Piledriver. Following the contest, Triple H settled into his role as Chief Operating Officer (COO) of WWE while the Undertaker went on his annual sabbatical until the following year’s Wrestlemania. Triple H returned to ring sooner, contesting Brock Lesnar at that year’s Summerslam pay-per-view.
8. The Ultimate Warrior vs. Hulk Hogan; Intercontinental/WWF Championship (Wrestlemania VI)
Match Background: This legendary contest came to fruition a week after the Ultimate Warrior and Hulk Hogan crossed paths at the Royal Rumble, with Hogan stating that he needed to know whether Hulkamania was more potent than the Power of the Warrior (yes, kayfabe was in full swing back then). A week later, WWF President Jack Tunney announced the match as the main event of Wrestlemania VI, adding that each man would put his respective championship on the line.
What Made The Match Great: To fully appreciate this contest, viewers must adjust their expectations relative to the era in which the match took place. During the late 1980s/early 1990s, few superstars were able to match Hogan’s charisma and larger-than-life persona. However, once the Ultimate Warrior burst onto the scene, fans were left wondering whether Hogan had finally encountered his equal.
While this match was not as substandard as 1987’s Andre the Giant-Hulk Hogan clash, this contest would fail to crack a top-75 list of greatest Wrestlemania matches based on in-ring prowess alone.
Nevertheless, fans were invested in the outcome of this contest. While the long-term implications of Warrior’s crowning moment didn’t pan out as WWE had probably hoped — this match was supposed to be an official passing of the torch– it did lend a genuinely iconic atmosphere to Wrestlemania VI.
Result and Aftermath: After avoiding a Hogan Leg Drop, The Ultimate Warrior executed a Big Splash that was just enough to keep Hogan down for the three count. After the match, Hogan presented the Ultimate Warrior with the WWF Championship as an outward sign of respect. As alluded to earlier, this match was supposed to be a passing of the torch. However, the relationship between Vince McMahon and the Ultimate Warrior soon disintegrated as back-and-forth disagreements eventually opened an irreparable fissure between the two men.
After a nine-month reign as WWE champion, The Ultimate Warrior lost his title to Sgt. Slaughter, who served as a transitional champion before dropping the title back to Hulk Hogan in the main event of Wrestlemania VII.
7. Chris Benoit vs. Shawn Michaels vs. Triple H; World Heavyweight Championship (Wrestlemania XX)
Match Background: The build up to the Triple Threat contest for the World Heavyweight Championship was both intriguing and convoluted. Chris Benoit, who had been performing on Smackdown!, earned his opportunity to challenge for the World Championship at Wrestlemania after defeating the Big Show during the final elimination of that year’s Royal Rumble contest. However, the existing clause didn’t specify which championship the winner of the Royal Rumble must challenge for, creating a loophole for Benoit to compete for Raw’s greatest prize.
Meanwhile, Shawn Michaels — citing their 10-year rivalry — insisted that he deserved the opportunity to challenge Triple H at Wrestlemania. Taking the situation into his own hands, Michaels delivered a Sweet Chin Music to Benoit before signing his name on the contract. After a grudge match between Benoit and Michaels on the following Raw, “Sheriff” Stone Cold Steve Austin decided that Triple H would defend his title against both Michaels and Benoit.
What Made The Match Great: Despite the Triple Threat’s bad reputation, the three participants used the match stipulation to perfection, wrestling to an accelerated pace and adding an element of unpredictability. Blood poured from each competitor’s face as each delivered devastating maneuvers out of nowhere, battering every wrestler’s body. Additionally, while most multi-dimensional feuds see their appeal diminished from overbooking, this match benefited from its multidimensional nature: Benoit’s ferocious desire to claim his place atop WWE’s mountain fused with Michaels and Triple H’s long-standing rivalry, introducing a fresh aspect to the latter’s feud.
Furthermore, the match featured three of the greatest in-ring performers in WWE history, each with contrasting in-ring styles. Unfortunately, since the bout, Benoit’s personal demons have completely overshadowed his moment in the sun, though that does not diminish the brilliance these three men delivered on this particular night.
Result and Aftermath: Chris Benoit denied Triple H’s bid to break the Crippler Crossface, forcing the champion to submit. Unfortunately, the sole highlight of Benoit’s reign as champion was his Wrestlemania victory, as Benoit embarked upon an underwhelming championship reign until he dropped the belt to Randy Orton at that year’s Summerslam. Following his title loss, WWE relegated Benoit to the midcard until the tragic murder-suicide that defines Benoit’s legacy.
6. Bret Hart vs. Stone Cold Steve Austin, No Disqualification Submission Contest (Wrestlemania XIII)
Match Background: After winning the King of the Ring Tournament and delivering the infamous Austin 3:16 promo that propelled him to main event status, Stone Cold Steve Austin began taunting an inactive Bret Hart, verbally baiting Hart into accepting his challenge for that year’s Survivor Series. Though Bret Hart would reign supreme at Survivor Series after countering a Million Dollar Dream into an improvisational roll-up, their rivalry would continue at the 1997 Royal Rumble match, where Austin emerged victorious after re-entering the ring despite having been eliminated by Hart.
Nevertheless, Hart would overcome his disappointment the next month. At In Your House: Final Four, Hart secured the vacated WWF Championship in a Four Corners match against Austin, the Undertaker and Vader, only to have Austin cost him his title the following night to Sycho Sid.
What Made The Match Great: Though the King of the Ring promo was Austin’s coming out moment, the war between Austin and Hart at Wrestlemania XIII was undoubtedly Austin’s coming out match. Austin’s effort cemented him as both a future main-event talent and a cornerstone for WWE to build its next generation around. Despite portraying a heel, Austin’s gutsy performance earned the allegiance of both the live audience and viewers at home. From an in-ring standpoint, the action and storyline were brilliantly executed, with Austin using anything at his disposal while also providing fans with one of the most iconic moments in WWE history.
Bleeding profusely yet refusing to concede victory, Austin passed out in lieu of submitting. Austin’s resilience and determination set a rare “double turn” into motion, an occasion that only transpires when the audience is so enamored with the superstar portraying the heel that they organically anoint him or her a fan favorite, subsequently vilifying whoever the supposed babyface is.
Result and Aftermath: Hart applied his patented Sharpshooter, incapacitating Austin. As mentioned above, WWE used this development to execute the rare double turn, seeing Austin settle into his anti-hero babyface role as Hart transitioned into an anti-American heel. Austin and Hart continued their rivalry, albeit with a reversal of roles, throughout the remainder of the year with Hart reforming the Hart Foundation.
Hart later defeated the Undertaker for the WWF Championship before dropping the title to Shawn Michaels during the infamous Montreal Screwjob. Meanwhile, Austin’s face turn helped lead the WWF into the Attitude Era, highlighted by his blood feud against WWF Chairman Vince McMahon. The rest is history.
5. Shawn Michaels vs Undertaker; Streak vs. Career Match (Wrestlemania XXVI)
Match Background: After earning a Slammy Award for Match of the Year following Wrestlemania 25, Michaels maintained that he could end The Undertaker’s vaunted Wrestlemania streak. Disappointed after dropping a hard-fought battle at the previous years’ Wrestlemania, Michaels proceeded to challenge The Undertaker to a rematch at the upcoming event, a proposal initially refused by “The Deadman.”
Michaels’ desire to defeat The Undertaker at Wrestlemania slowly mutated into an obsession. “The Heartbreak Kid” twice fell short in opportunities to challenge ‘Taker, first losing the Royal Rumble match before falling flat in his Elimination Chamber qualifying match.
Undeterred, Michaels returned to the Elimination Chamber match unannounced before delivering a Sweet Chin Music to The Undertaker, costing ‘Taker his World Heavyweight Championship after Chris Jericho crawled over to pin the subdued legend.
The title loss prompted The Undertaker to accept Michaels’ Wrestlemania challenge. Michaels, emboldened by the prospect of a marquee match, volunteered to put his wrestling career on the line, claiming his career would no longer be worth continuing if he failed to defeat the Undertaker at the “Granddaddy of Them All.”
What Made The Match Great: Similar to their previous encounter at Wrestlemania 25, the Undertaker and Michaels delivered a match flooded with suspense and exhilarating moments. However, an added stipulation kept this match fresh, as fans were torn between supporting either the Undertaker’s legendary streak or Michaels’ storied career.
Emotion also ran wild in this contest. By the end of a grueling, 30-minute battle, both competitors leaned one another for both mental and physical support.
Result and Aftermath: Following two consecutive jumping Tombstone Piledrivers, The Undertaker ended Michaels’ career. The next night on Raw, Michaels addressed the WWE Universe in his farewell speech during an episode dedicated to highlighting Michaels’ career accomplishments. The contest earned Match of the Year honors for the second consecutive year.
4. Stone Cold Steve Austin vs The Rock; No Disqualification (Wrestlemania X7)
Match Background: The highest-ranked Wrestlemania main event on this list, Stone Cold Steve Austin and The Rock concluded what is widely regarded as the greatest Wrestlemania of all time. A slow-burning extension of their feud from 1999 when Austin defeated the Rock for the WWF Championship at both Wrestlemania XV and the 1999 edition of Backlash, the “Texas Rattlesnake” earned the right to challenge the Rock by last eliminating Kane to win the 2001 Royal Rumble contest.
The Rock entered the feud as the first-ever six-time WWF Champion after defeating Kurt Angle at the 2001 edition of No Way Out. Meanwhile, Austin remained disconnected from the WWE Title scene as he waged war against Triple H in the since-immortalized Three Stages of Hell Match.
In an effort to stoke tensions between his two premier performers, WWE CEO Vince McMahon appointed Austin’s wife as The Rock’s personal manager.
Austin pledged hell should any harm befall his wife on The Rock’s watch, a promise Austin followed through on after The Rock failed to prevent Angle from trapping Debra in the Ankle Lock. This match is also celebrated for its pre-match promo, which featured Limp Bizket’s “My Way.”
What Made The Match Great: Many dream matches between behemoths of the industry have come to fruition of late, with Hogan vs. The Rock and The Rock vs. John Cena coming to the forefront of the mind. However, a match between two established WWE icons rarely takes place during the prime of both competitors’ careers.
One of those rare occasions transpired in 2001 at the Astrodome in Houston, Texas. The match captured the anticipation of The Ultimate Warrior vs. Hogan while replicating the in-ring prowess of Savage vs. Steamboat.
Both men poured their hearts into their performance. After failing to subdue Austin with the Rock Bottom, The Rock planted Austin with a Stone Cold Stunner, sending the crowd into a frenzy. Austin soon returned the favor, performing his own version of the Rock Bottom on the battered champion.
Austin and The Rock also propelled the false finish to an unprecedented level, leaving fans flabbergasted as each man exhibited the tenacity befitting of a WWE Title match on the industry’s largest stage.
Result and Aftermath: Austin received considerable help from both McMahon and a steel chair to incapacitate The Rock, subsequently initiating a heel turn that sent tremors throughout the WWE Universe. Austin’s next feud saw him team with former rival Triple H against Kane and The Undertaker, collectively known as the Brothers of Destruction.
With the benefit of retrospect, Austin’s heel turn was a creative misfire. At the time, Austin anchored the company as a relatable anti-hero, providing WWE with a moral counterpoint to both its biggest babyfaces and heels.
Austin remained a heel throughout the ill-fated WCW invasion angle, which struggled to compensate for the lack of star power on the WCW/ECW side. Austin defected to the since-defunct WCW brand despite serving as the face of WWE during the Monday Night Wars.
The Rock defeated Booker T for the WCW Championship at Summerslam of that year. Coincidentally, both Austin and The Rock lost their titles to Chris Jericho at December’s Vengeance pay-per-view in a tournament to crown WWE’s first-ever Undisputed Champion.
3. TLC 2 (Wrestlemania X-7)
Match Background: In the midst of arguably the greatest period for tag team wrestling in WWE history, three equal yet vastly different sets of brothers — The Hardy Boyz, The Dudley Boyz and Edge & Christian — stood atop the proverbial tag team mountain. Within one month of Wrestlemania X-Seven, the three teams exchanged the Tag Teams Championships three times, with the championships starting in the possession of the Hardy Boyz before transitioning to Edge & Christian and finally landing with D-Von and Bubba Ray Dudley.
During the spring of 2000, each team adopted a unique foreign object into their arsenal. Remaining consistent with their high-flying nature, the Hardy Boyz incorporated ladders into their gimmick. Meanwhile, the Dudley’s remained true to their love for driving their opponents through tables while Edge & Christian punished opponents with their trademark Conchairto maneuver.
The ongoing rivalry over the Tag Team Championships between these three teams led to the first-ever Tables, Ladders and Chairs match at SummerSlam 2000, a match viewed with such reverence that fans demanded an encore.
What Made The Match Great: Pure, unadulterated carnage. TLC 2 featured nine performers–Lita, Rhyno and Spike Dudley each interfered in the contest–willing to sacrifice their well-being for the sake of entertaining their audience. Prior to Wrestlemania X-7, many fans assumed the original TLC match would never be surpassed, convinced the original represented the apex of tag team wrestling.
However, through sheer determination and steely resolve, the three participating teams put on a spectacle still cited as one of the most entertaining, chaotic matches in WWE history.
Result and Aftermath: After surviving one of the most brutal contests in WWE history, Christian ascended the ladder with Rhyno’s assistance to retrieve the Tag Team Championships for his team. Unfortunately, the momentum these teams should have enjoyed across the following months was sacrificed to advance the storyline centered around Austin and his new alliance with McMahon and Triple H.
Sixteen days after emerging victorious at Wrestlemania X-7, Edge and Christian dropped their titles to the Brothers of Destruction (who would then feud with The Two-Man Power Trip) approximately three weeks later. By the end of the year, both Edge & Christian and the Hardy Boyz broke up.
Remarkably enough, each competitor went on to achieve success as a singles competitor. Edge paced all competitors with 11 World Title wins while Jeff Hardy and Christian won three and two top titles, respectively. Matt Hardy won the top title on the since-defunct ECW brand.
While Bubba Ray Dudley never won a top title under the WWE banner, he became a cornerstone of TNA during the promotion’s peak. D-Von Dudley never won a singles title while working for WWE, though he claimed the TNA Television Championship twice.
2. Kurt Angle vs. Shawn Michaels (Wrestlemania XXI)
Match Background: An inter-promotional contest during the Raw/Smackdown brand extension era, this rivalry commenced at the 2005 Royal Rumble, when Angle attacked Michaels after Michaels eliminated him from the contest.
The following month, after failing in his bid to represent Smackdown in the brand’s Wrestlemania main event, Smackdown general manager Teddy Long informed Angle that Michaels challenged him to a match at Wrestlemania, a challenge accepted only after Angle ambushed Michaels.
Angle furthered his heel persona with some excellent underhanded tactics. The Olympic Gold Medalist was determined to prove his superiority by embarking on a mission to replicate Michaels’ career accomplishments in a fraction of the time.
In the weeks leading up to Wrestlemania, Angle spoofed Michaels’ entrance song, won a ladder match and defeated Michaels’ former tag team partner Marty Jannetty via submission.
What Made The Match Great: This match featured one of the industry’s greatest in-ring technicians go toe-to-toe against arguably the greatest performer and showman in professional wrestling history.
The in-ring styles of the two men complemented one another perfectly. However, what earned this match the No. 2 slot was the seamless countering. By the midway point of the match, the Staples Center crowd was on its feet, applauding each man for their remarkable efforts.
For a while, this match was blacklisted by WWE due to Angle’s contractual obligations to TNA, depriving the contest of the recognition it warranted. However, Michaels vs. Angle has since been enshrined in WWE lore following Angle’s return to WWE.
If you haven’t witnessed the match between Angle and Michaels at Wrestlemania XXI, this writer implores you to watch it immediately.
Result and Aftermath: After executing a Sweet Chin Music that only netted him a two-count, Michaels staggered to his feet before an opportunistic Angle trapped Michaels in an Ankle Lock. As a writhing Michaels’ desperately attempted to either reach the ring ropes or counter the hold, Angle wrapped his body around Michaels’ leg for the submission victory
Unfortunately, due to the inter-promotional nature of this contest, both superstars failed to capitalize on the momentum in the immediate aftermath of this epic encounter. Michaels partnered with Hulk Hogan to defeat the heel tag team of Hassan Muhammad and Daivari in an underwhelming contest.
Angle proceeded to participate in an equally underwhelming feud against Booker T. Nevertheless, Michaels and Angle rehashed their rivalry in time for Vengeance 2005 after Raw general manager Eric Bischoff drafted Angle to his brand.
1. Shawn Michaels vs. The Undertaker (Wrestlemania XXV)
Match Background: The first of two Wrestlemania encounters between The Undertaker and Michaels didn’t require added stipulations to validate its position on the Wrestlemania 25 card. Instead, their encounter operated as a contest between two of the greatest performers ever to grace a professional wrestling ring.
In the build to Wrestlemania 25, the opportunity to end The Undertaker’s legendary Wrestlemania win streak assumed center stage, with Michaels, John “Bradshaw” Layfield and Vladimir Kozlov each jockeying for the honor. Michaels challenged JBL to a rematch of their clash at No Way Out under the stipulation that the winner would earn the right to face The Undertaker at Wrestlemania 25.
However, after defeating JBL, Michaels learned that he also needed to overcome Kozlov, who he defeated on the ensuing Monday Night Raw. The next week, The Undertaker and Michaels teamed to defeat JBL and Kozlov in a tag team contest. After the match, Michaels assaulted The Undertaker, leading to the two legends engaging in psychological warfare
What Made The Match Great: Quite honestly, everything about this match is enthralling, from the multi-layered storytelling to the in-ring chemistry shared between the two competitors. Both men abandoned reservations, performing an array of devastating and jaw-dropping maneuvers only to find themselves unable to disable their opponent. False finishes were used liberally but expertly, setting the foundation for a level of suspense that has seldom, if ever, been matched in wrestling history.
Result and Aftermath: As any casual wrestling fans can probably discern, The Undertaker reigned supreme in this contest after an exhilarating series of events that saw ‘Taker counter a Moonsault into the definitive Tombstone Piledriver. Following the match, each man went on a four-month hiatus.
Michaels resurfaced first to reform D-Generation X with Triple H. However, at that year’s Slammy Awards, Michaels and Undertaker would win Match of the Year, setting into motion a series of events that would lead to their eventual rematch.