One of the most iconic figures in WWE history, The Undertaker made his television debut on November 22, 1990, at Survivor Series as Ted DiBiase’s mystery partner. Within minutes, he eliminated Koko B. Ware and Dusty Rhodes — the beginning of a legendary three-decade run.
More than his seven world championships, The Undertaker became defined by his unparalleled 21–0 undefeated streak at WrestleMania, a run that stood until Brock Lesnar ended it at WrestleMania XXX. He also wrestled in the ’80s, ’90s, ’00s, ’10s, and ’20s with almost no interruption, innovating signature match types like Hell in a Cell, the Casket Match, the Buried Alive match, and the Last Ride match.
And while his early years featured a string of slow, lumbering opponents (yes, Giant Gonzales, we mean you), the late ’90s onward saw The Deadman consistently deliver classics.
Here’s a chronological look at some of his most memorable battles.
Survivor Series (1990) – Debut Match
As Ted DiBiase’s “mystery partner” in the Million Dollar Team, The Undertaker made an unforgettable entrance with Brother Love at his side. His size, aura, and dominance were immediate, eliminating Koko B. Ware and Dusty Rhodes before being counted out. The Phenom had arrived — and WWE would never be the same.
Bad Blood: In Your House (1997) – Hell in a Cell vs. Shawn Michaels
The first-ever Hell in a Cell match was born from months of chaos. After Shawn Michaels cost The Undertaker the WWF Championship at SummerSlam 1997, the two clashed at In Your House: Ground Zero, which ended in a no-contest. A new, enclosed structure was created for their rematch — larger and more dangerous than a standard steel cage.
Paul Bearer, still fuelling the fire, teased that Kane — Undertaker’s half-brother thought to be dead — was alive and coming for him. That prophecy came true mid-match when Kane debuted, tearing off the Cell door and costing The Undertaker the win.
King of the Ring (1998) – Hell in a Cell vs. Mankind
The most infamous Hell in a Cell bout in WWE history. Mankind (Mick Foley) challenged Undertaker after weeks of attacks and alliances involving Kane and Paul Bearer.
On June 28, 1998, The Undertaker threw Mankind from the top of the Cell through the announce table — a moment etched into wrestling history. Minutes later, he choke-slammed him through the Cell roof. Despite the punishment, Undertaker secured the pinfall in a brutal, career-defining spectacle.
Vengeance (2002) – Triple Threat for the Undisputed Championship
After retaining the Undisputed Championship against Triple H at King of the Ring 2002, The Undertaker was dragged into a feud with The Rock and Kurt Angle. When a SmackDown title match between Undertaker and Angle ended in a double decision, Vince McMahon added both challengers to the Vengeance main event.
In a high-paced triple threat, all three exchanged near-falls until The Rock ultimately pinned Kurt Angle to win the championship, ending Undertaker’s reign.
SmackDown (September 4, 2003) – WWE Championship vs. Kurt Angle
Fresh off his SummerSlam victory over A-Train, Undertaker earned a WWE Championship shot by defeating Brock Lesnar and Big Show in a triple threat. Facing Kurt Angle on SmackDown, the two technical masters went to war in a rare TV main event for the title, ending in controversy but showcasing Undertaker’s adaptability.
SummerSlam (2008) – Hell in a Cell vs. Edge
In 2008, Undertaker and Edge clashed repeatedly for the World Heavyweight Championship. After losing a TLC match at One Night Stand (which forced him out of WWE), Undertaker returned when Vickie Guerrero — furious at Edge’s infidelity — reinstated him and booked them in a Hell in a Cell match.
The match at SummerSlam was a violent conclusion to their feud, ending with Undertaker chokeslamming Edge from the top of a ladder through the ring itself.
WrestleMania XXV (2009) – vs. Shawn Michaels
At 16–0, The Undertaker’s WrestleMania streak became the ultimate prize. Shawn Michaels earned the right to challenge him and spent weeks playing psychological games. The match itself became an instant classic, earning the 2009 Match of the Year Slammy Award and widespread acclaim as one of the greatest WrestleMania bouts ever.
WrestleMania XXVI (2010) – Streak vs. Career vs. Shawn Michaels
One year later, Michaels demanded a rematch. This time, his career was on the line. After costing Undertaker the World Heavyweight Championship at Elimination Chamber, Michaels got his wish — a no-disqualification war at WrestleMania XXVI.
Undertaker won again, ending Michaels’ in-ring career and delivering an emotional farewell moment.
WrestleMania XXVII (2011) – No Holds Barred vs. Triple H
In February 2011, both Undertaker and Triple H returned on Raw and silently agreed to face each other at WrestleMania. Their No Holds Barred contest was a hard-hitting, weapon-filled brawl that left Undertaker victorious — but so battered he needed to be stretchered out, a first in his career.
WrestleMania XXVIII (2012) – Hell in a Cell vs. Triple H (Shawn Michaels as Referee)
A year later, Undertaker demanded a rematch to erase the image of being stretchered away. Triple H accepted, with the twist that Shawn Michaels would be the special guest referee. Branded “The End of an Era,” this Hell in a Cell showdown was a brutal 30-minute war. Undertaker moved to 20–0, and all three men stood together in a rare curtain-call moment.
WrestleMania 29 (2013) – vs. CM Punk
After CM Punk won a fatal four-way to earn the WrestleMania shot, the rivalry turned personal with the real-life passing of Paul Bearer. Punk taunted Undertaker relentlessly, even stealing and desecrating the urn.
At WrestleMania, Undertaker overcame Punk’s mind games in a technical and emotional battle, extending his streak to 21–0 — his final WrestleMania win before the streak’s eventual end.
WrestleMania XXX (2014) – vs. Brock Lesnar
Perhaps the most shocking moment in modern WWE history. Brock Lesnar, already a dominant force, became the first man to pin The Undertaker at WrestleMania. The stunned silence of the crowd — and the 21–1 graphic — remains one of WWE’s most replayed moments.
WrestleMania 36 (2020) – Boneyard Match vs. AJ Styles
In his final match, Undertaker faced AJ Styles in a cinematic Boneyard Match filmed during the COVID-19 pandemic. Mixing fight choreography, supernatural elements, and character-driven storytelling, it was the perfect send-off. The Deadman buried Styles, rode off into the night, and later announced his retirement.
The Legacy of The Deadman
From supernatural beginnings to biker reinvention, from awkward slogs with immobile giants to instant classics with the best in the business, The Undertaker’s career is unmatched in wrestling history. He defined eras, innovated match types, and created moments that will be told and retold for generations.
