The Undertaker’s Greatest Wrestling Matches of All Time

Ask any fan for a list of the top wrestlers of all time, and everyone will have a few different answers. Without fail, though, a name that will always wind up on any wrestling viewer’s list of top performers is WWE’s Phenom, The Undertaker.

One of the company's premiere players since the early ‘90s, The Dead Man has become a mainstay attraction for WWE television. A cornerstone of WWE programming from the promotion's Golden Age up to his eventual retirement in 2020, the Phenom has the honor of being one of the top faces for WWE for 30 years. Transitioning from one gimmick to one another, his consistent reliance on the Dead Man character has made him an undeniable legend in the wrestling industry, influencing entire generations of younger talents who followed in his footsteps.

Given how long The Undertaker has been in WWE, it’s easy to expect he’s had matches with almost every major star who walked through WWE’s front doors, from Attitude Era personalities like The Rock and “Stone Cold” Steve Austin to Ruthless Aggression Era performers like Edge and Randy Orton.

From some of the Phenom’s most lauded matches at WrestleMania up to his Attitude Era bouts under his “Big Evil” moniker, here are some of the Undertaker’s greatest matches, ranked from best to worst.

The Undertaker vs. Shawn Michaels (WrestleMania 25)

The Undertaker, Mankind, Mick Foley
Image Credit: World Wrestling Entertainment.

One can’t mention The Undertaker without discussing “the Streak” – the unprecedented series of victories Undertaker held at WWE’s flagship pay-per-view, WrestleMania. And of course, one can’t discuss the Streak without bringing up The Undertaker’s finest WrestleMania match against his most famous rival, Shawn Michaels, at WrestleMania 25.

Having sported almost supernatural invulnerability every WrestleMania season, The Undertaker took to defending his undefeated Streak for over two decades, meeting all kinds of worthy challengers on the road to WrestleMania. Of these prospective contenders, Shawn Michaels posed perhaps the greatest threat to ‘Taker’s Streak, maintaining the same high level of physical performances every WrestleMania as his undead counterpart. In the subsequent match, Michaels and ‘Taker had a certified classic of a row, filled with near-falls, risky bumps, and out-of-nowhere finisher deliveries. It’s not only the best match in either man’s career but perhaps the greatest match in WrestleMania history.

The Undertaker vs. Mankind (King of the Ring 1998)

The Undertaker vs. Mankind King of the Ring 1998
Image Credit: World Wrestling Federation.

While Shawn Michaels versus Undertaker at WrestleMania is the most athletic match in the Demon from Death Valley’s career, The Undertaker versus Mankind at 1998’s King of the Ring is without a doubt the most noteworthy match ‘Taker has ever been involved in. Among the most shocking and unpredictable bouts of the Attitude Era – a period that prided itself on delivering shocking and unpredictable matches – the moment Undertaker sent Mankind crashing to the floor from the top of the Cell will forever live in infamy as one of the riskiest bumps in professional wrestling history.

Sacrificing life and limb for the entertainment of the fans, Undertaker and Mick Foley took literal years off their lives in their clash at the ‘98 King of the Ring. With Foley completing not one, but two heart-stopping falls that could have killed him, it’s a match that leaves viewers shaking your head, admiring the tenacity and toughness of both men, garnering a renewed appreciation for pro wrestling and all the risks involved.

The Undertaker vs. Shawn Michaels (WrestleMania XXVI)

The Undertaker, Shawn Michaels
Image Credit: World Wrestling Entertainment.

Looking to redeem his previous loss at WrestleMania 25, a vendetta-driven Shawn Michaels challenged the Phenom to a rematch at 2010’s WrestleMania XXVI, putting his career on the line for a chance to break ‘Taker’s legendary undefeated Streak. Though their first outing at WrestleMania 25 might have been the more momentous of the two, HBK and ‘Taker’s WrestleMania XXVI encounter benefitted from tremendous storytelling and emotion.

With an obsessive Michaels pulling out every trick in the book to overcome his longtime nemesis, The Undertaker tapped into every reserve of energy he had to stay in the match, dialing his usual WrestleMania performances up to a solid 10. Echoing Michaels’ own match with Ric Flair two years prior, a beaten but not yet broken Michaels preferred going out on his terms, slapping The Undertaker in one last act of defiance. The resulting match had a near cinematic quality, concluding the Heartbreak Kid’s iconic career in the best way possible.

The Undertaker vs. Shawn Michaels (In Your House: Badd Blood)

Undertaker vs. Shawn Michaels Badd Blood In Your House
Image Credit: World Wrestling Federation.

While Shawn Michaels and The Undertaker’s rivalry will forever evoke their later WrestleMania bouts, it’s also worth highlighting how fantastic their earlier clashes at the tail end of the 1990s. With Shawn Michaels completing his heel turn and forming D-Generation X in the summer of 1997, the Heartbreak Kid and his faithful gang found themselves facing off against The Undertaker throughout the remainder of the year.

After a terrific but inconclusive outing at Ground Zero: In Your House, The Undertaker challenged Michaels to a match at In Your House: Badd Blood to settle their feud. The first match of its kind, it made use of its unprecedented nature to add twists and turns around every corner. Battling inside the ring and both outside of and on top of the Cell, The Undertaker proceeded to beat Michaels senseless for the next 30 minutes, only stopping with the shocking debut of his on-screen brother, Kane. It’s a great match from Undertaker’s prime Attitude Era years, existing today as one of the best matches of all time.

The Undertaker vs. Triple H (WrestleMania XXVIII)

The Undertaker, Triple H
Image Credit: WWE.

Like most gimmick-heavy wrestlers, The Undertaker is synonymous with a handful of specialty matches in WWE: the Buried Alive match, the Casket match, and so forth. With that in mind, it should come as no surprise that a variety of famous stars challenged ‘Taker to these matches of the years, hoping to beat the Phenom at his own game.

Following his loss at WrestleMania XXVII one year earlier, Triple H again faced off against The Undertaker at the following year’s WrestleMania XXVIII, this time at the behest of The Undertaker himself. With Shawn Michaels acting as the special guest referee, the Game and the Dead Man had an otherwise stellar match together, relying more on emotion and theatrics than intense physical brawling. The combination gave fans another satisfactory entry in The Undertaker’s undefeated Streak.

The Undertaker vs. Edge (WrestleMania XXIV)

Th Undertaker, Edge
Image Credit: World Wrestling Entertainment.

Before reigniting his '90s-era feuds with Shawn Michaels and Triple H at WrestleMania, The Undertaker engaged in an epic rivalry with rising Ruthless Aggression star Edge in the latter half of the 2000s. Capturing the World Heavyweight Championship from the Phenom using his Money in the Bank briefcase, Edge used every dubious trick in the book to defend his title against ‘Taker, leading to their eventual encounter in the main event of WrestleMania XXIV.

In the subsequent “Streak vs. Championship match,” the Ultimate Opportunist tried everything he could to defeat The Undertaker, hoping to retain his title and become the first man to defeat The Undertaker at WrestleMania. Bashing The Undertaker’s head in with a ringside camera and using his signature Edgeheads (Curt Hawkins and Zack Ryder) as distractions, it seemed that Edge might do the impossible – only for The Undertaker to lock in his submission hold at the last possible moment. The match served as the highlight of The Undertaker’s 2008 feud with Edge – even if their simmering feud only seemed to be getting started.

The Undertaker vs. Brock Lesnar (No Mercy 2002)

The Undertaker, Brock Lesnar
Image Credit: World Wrestling Entertainment.

In mid-2002, the landscape of WWE seemed to be changing, the faces of WWE’s old guard (The Rock, Steve Austin, and The Undertaker) competing against the rising talents of the decade’s Ruthless Aggression Era. As proof of this fact, The Undertaker soon encountered WWE’s Next Big Thing, Brock Lesnar, in a series of matches for Lesnar’s WWE Championship.

Following an inconclusive bout at Unforgiven, The Undertaker and Lesnar squared off in a rematch at No Mercy, this time brawling within The Undertaker’s signature structure. One of the most intense and violent matches in WWE history, The Undertaker and Lesnar engaged in a fierce back-and-forth slew of offensive maneuvers, leaving it out all in the ring in their match-up together. In terms of pure physicality alone, it’s perhaps the best match the two ever had against one another – whether we’re talking about their 2002 feud or their later rivalry in the mid-2010s.

The Undertaker vs. Randy Orton (WrestleMania 21)

The Undertaker, Randy Orton
Image Credit: World Wrestling Entertainment.

Breaking off from his former stable mates in Evolution, Randy Orton doubled down on his own “Legend Killer” character, targeting numerous WWE legends from retired stars like Jake Roberts to active performers like Mick Foley. At the beginning of 2005, young Orton set his sights on The Undertaker, hoping to dethrone the Phenom on the grandest stage.

Competing in the first of a series of matches that lasted over the course of the year, Orton and ‘Taker’s first bout at WrestleMania 21 serves as another high point in their year-long feud together. With Orton hitting a sudden RKO on The Undertaker mid-air during a chokeslam, it seemed like Orton had secured his legacy in WWE, ending ‘Taker’s undefeated Streak for good. As it happened, The Undertaker had one final burst of energy, bouncing back long enough to deliver a thunderous Tombstone to the Legend Killer for the one, two, three.

The Undertaker vs. Batista (WrestleMania 23)

The Undertaker, Dave Bautista
Image Credit: World Wrestling Entertainment.

Winning the Royal Rumble at the start of 2007, The Undertaker earned the right to challenge either John Cena, Bobby Lashley, or Batista for a championship match at WrestleMania 23. In a surprise twist, ‘Taker opted to take on the Animal for the World Heavyweight Championship, the two facing off in one of the standout matches at the pay-per-view that year.

Among the most physical matches in Undertaker’s WrestleMania performance history, The Undertaker and Batista proceeded to lay the smackdown on one another throughout their entire 15-minute bout, making a short match feel so much more epic and long-lasting in scope. While they might’ve been better off closing out the show, ‘Taker and Batista nevertheless had a dream match in the making, culminating in a rivalry that lasted throughout 2007.

The Undertaker vs. Bret Hart (SummerSlam 1997)

The Undertaker, Bret Hart
Image Credit: World Wrestling Federation.

One of the favorite recurring opponents of The Undertaker came in the form of his New Generation/Attitude Era counterpart, Bret “The Hitman” Hart. Meeting for the first time in 1992, ‘Taker and Hart later rehashed their feud against one another in the early days of the Attitude Era, culminating in their fiery bout in the main event of 1997’s SummerSlam.

With Hart’s foremost rival, Shawn Michaels, acting as the special guest referee, Hart and ‘Taker took significant leeway in their match-up here, bending the rules and taking advantage of Michaels’ lax outlook on disqualifications and count-outs. Playing to both men’s offensive styles, the bout alternated between Hart’s preference for technical wrestling and submission holds and ‘Taker’s more hard-hitting jabs and decisive offensive maneuvers. Using his wiles to enrage HBK, Hart manipulated Michaels into hitting ‘Taker in the head with a chair, allowing him to score the pinfall victory and obtain his fifth WWF Championship in the process.

The Undertaker vs. Kurt Angle (No Way Out 2006)

The Undertaker, Kurt Angle
Image Credit: World Wrestling Entertainment.

With shades of his previous encounters against Bret Hart in the ‘90s, The Undertaker found himself facing off against the Olympic Gold Medalist Kurt Angle from the early 2000s until Angle’s departure from WWE in 2006. For as many matches as they had, however, the crowning moment in The Undertaker and Kurt Angle’s rivalry came in the main event of No Way Out 2006, with Angle’s World Heavyweight Championship laying in the balance ahead of WrestleMania 22.

In one of The Undertaker’s most underrated performances, ‘Taker opted to utilize a more traditional technical-based wrestling style, emblematic of Angle’s own background in amateur wrestling. The resulting match saw the two men alternate between suplexes, submission holds, and smooth reversals, leading Angle to secure a victory with a sudden roll-up, countering Undertaker’s devastating-looking triangle choke in the most creative way imaginable.

The Undertaker vs. Edge (SummerSlam 2008)

The Undertaker, Edge
Image Credit: World Wrestling Entertainment.

Though Undertaker and Edge’s feud began in 2007, the two men engaged in a number of excellent matches for the next year, including their earlier encounter at WrestleMania XXIV, their TLC match at One Night Stand, and their conclusive match at SummerSlam 2008.

Serving as the final chapter in their epic saga, Undertaker returned to WWE after being reinstated by Vickie Guerrero (as part of the match stipulation at One Night Stand, Undertaker had been forced to leave the promotion after being beaten by Edge for the World Heavyweight Championship). Meeting in ‘Taker’s specialty match, Undertaker proceeded to beat Edge down for the next half hour, not unlike ‘Taker’s own decisive smackdown of Shawn Michaels at Badd Blood: In Your House. Introducing chairs, ladders, and tables to the match, the main event of SummerSlam 2008 felt like a hybrid match, allowing for some entertaining spots between ‘Taker’s most notable Ruthless Aggression Era foe.

The Undertaker vs. Edge (One Night Stand 2008)

The Undertaker, Edge
Image Credit: World Wrestling Entertainment.

After losing the World Heavyweight Championship in the closing moments of WrestleMania XXIV, Edge used his on-screen romance with SmackDown general manager Vickie Guerrero to strip ‘Taker of the title after several unsuccessful attempts to reclaim the championship. With the World Heavyweight Championship now available for anyone to claim, Edge and ‘Taker once again squared off for the belt, this time in a Tables, Ladders, and Chairs match at 2008’s One Night Stand.

Relying on his intimate knowledge of the TLC match – a match he helped create – Edge also called in heavy support from his and Guerrero’s La Familia stable. The continuous onslaught from Edge’s allies proved decisive, with the hard-fitting ‘Taker becoming overcome by the joint interference of Curt Hawkins, Zack Ryder, Chavo Guerrero, and Bam Neely. Though unsuccessful in his attempts to reclaim the World Heavyweight Championship, The Undertaker’s performance in this match served as a highlight of his career in the late 2000s.

The Undertaker vs. Kane (WrestleMania XIV)

The Undertaker, Kane
Image Credit: World Wrestling Federation.

Debuting at the very end of Badd Blood: In Your House, The Undertaker’s long-lost brother, Kane, became a recurring thorn in The Undertaker’s side, interfering with his matches and costing him a WWF Championship victory over Shawn Michaels at Royal Rumble 1998. Having grown addled by his brother’s constant appearances, The Undertaker agreed to a match that pitted brother against brother at WrestleMania XIV.

In a bout that possessed an almost supernatural aura around it, The Undertaker versus Kane at WrestleMania XIV also earns the distinction of being the absolute best match in the brothers’ decade-long feud against one another. Utilizing near-identical offensive move sets, the two siblings traded clubbing blows, Chokeslams, flying clotheslines, and devastating-looking Tombstone piledrivers, all to little effect. Only after a trifecta of Tombstones did The Undertaker lay his brother to rest, marking the prologue to a long, epic sibling rivalry in the years to come.

The Undertaker vs. Jeff Hardy (Raw)

The Undertaker, Jeff Hardy
Image Credit: WWE.

In the early summer of 2002, The Undertaker competed against his ‘90s rival, Hulk Hogan, defeating the former face of WWE for the promotion’s Undisputed Championship. In the weeks that followed, Undertaker defended his title against numerous WWE talents, ranging from ECW veterans like Rob Van Dam to up-and-coming stars like Jeff Hardy, the latter of whom met ‘Taker in a Ladder match in July on Raw.

In one of the best main events in Raw’s history, Hardy – known for his tenure as one-half of the Hardy Boyz at this point – came close to beating Big Evil, flying off the tops of ladders and using chair shot after chair shot to even the odds against the Phenom. Though unsuccessful, the underdog Hardy emerged from the match looking like a guaranteed champ in the making, earning the ultimate sign of respect from Undertaker for his tenacity, resourcefulness, and willingness to go to extremes in his quest for the WWE Championship.

Richard Chachowski is a freelance writer based in New Jersey. He loves reading, his dog Tootsie, and pretty much every movie to ever exist (especially Star Wars).