Top 20 Matches Of The Undertaker’s WWE Career
20- The Undertaker vs. AJ Styles - WrestleMania 36 (Boneyard Match)
The Undertaker's final WWE match was a cinematic masterpiece filmed off-site in a cemetery-like setting. This "Boneyard Match" allowed for creative storytelling and action, perfectly blending a brawl with a horror movie aesthetic. It brought back elements of The Undertaker's "American Bad Ass" persona, culminating with him burying AJ Styles in a grave of dirt. The unique presentation provided a compelling and fitting final chapter for The Phenom's career.
19- The Undertaker vs. Edge - One Night Stand 2008 (TLC Match)
In a high-stakes bout for the vacant World Heavyweight Championship, Vickie Guerrero stipulated that if The Undertaker lost, he would be fired from WWE. This TLC match, featuring interference from La Familia, was a chaotic spectacle. Edge ultimately defeated The Undertaker after a series of brutal ladder and table spots, leading to a temporary departure for The Phenom as part of the storyline.
18- The Undertaker vs. Kane - WrestleMania 14
The long-awaited first-ever in-ring match between the "Brothers of Destruction" was a spectacle. The emotional and personal feud, built around Kane's debut and desire for revenge, drove this dramatic battle. The Undertaker required three Tombstone Piledrivers to finally defeat the unstoppable Kane. The match established Kane as a legitimate monster and gave The Streak one of its most compelling, emotionally charged victories.
17- The Undertaker vs. Randy Orton - WrestleMania 21
This match was the beginning of the "Legend Killer" Randy Orton's quest to end The Streak. The young Orton was a credible threat, and the match was built on multiple dramatic near-falls and high spots, including an incredible RKO counter. Orton's early attempts to defeat Taker established the WrestleMania streak as the most valuable prize in the industry. The Undertaker ultimately hit a Tombstone to defeat the young superstar to go 13-0 at WrestleMania.
16- The Undertaker vs. Bret Hart - SummerSlam 1997
This WWE Championship match featured Shawn Michaels as the special guest referee, adding tremendous tension to the proceedings. The Undertaker and Bret "The Hitman" Hart delivered a fantastic psychological contest. The match concluded in a controversial fashion when Michaels accidentally struck The Undertaker with a chair meant for Hart, allowing Hart to win the title. This chaotic finish set up the future, historic rivalry between Taker and HBK.
15- The Undertaker vs. Batista - WrestleMania 23
After winning the 2007 Royal Rumble, The Undertaker chose to challenge Batista for the World Heavyweight Championship. This was a surprisingly fast-paced and physical brawl, shattering expectations for two powerful big men. Both stars delivered exceptional performances, with the crowd heavily invested in the outcome. The Undertaker ultimately secured the pinfall to win the world title, further extending The Streak to 15-0 in an excellent match.
14- The Undertaker vs. Kurt Angle - No Way Out 2006
This bout is a non-WrestleMania gem, a technical wrestling clinic for the World Heavyweight Championship. Kurt Angle and The Undertaker put on an incredible display of chain wrestling, counters, and submissions. Angle narrowly won by pinning Taker while simultaneously applying the Ankle Lock, a testament to their exceptional in-ring chemistry. It remains a must-watch match for its sheer athletic quality and suspenseful finish.
13- The Undertaker vs. Jeff Hardy - Raw (Ladder Match - 2002)
Often heralded as Jeff Hardy's breakout performance, this Ladder Match for the Undisputed Championship was an exhilarating display of athleticism and heart. Hardy, a major underdog, constantly thwarted The Undertaker with incredible resilience. Despite losing, Hardy earned The Undertaker's respect, who raised Hardy's hand in a powerful, emotional moment. The match is a pivotal turning point in Hardy's singles career. Moreover, the impact of this bout was increased further with Taker being a heel and still raising Hardy's hand and Jim Ross' explosive commentary.
12- The Undertaker vs. Brock Lesnar - No Mercy 2002 (Hell in a Cell)
This early encounter between The Undertaker and a young, dominant Brock Lesnar was a visceral, bloody Hell in a Cell match for the WWE Championship. Lesnar, showcasing his brutality, left The Undertaker a bloody mess, symbolizing the passing of the guard. Despite Taker's valiant fight, Lesnar pinned him to retain the title, solidifying his status as "The Next Big Thing" and producing a classic, hardcore Cell match.
11- The Undertaker vs. Brock Lesnar - Hell in a Cell 2015
The second Hell in a Cell match between these two behemoths 13 years after their first was also a brutally physical war, aiming to settle their long-standing feud. The match involved vicious chair shots, exposed turnbuckles, and Lesnar ripping the mat up to expose the wooden ring boards. Lesnar ultimately won this blood-soaked encounter, which served as one of the final truly punishing battles of The Undertaker's storied career.
10- The Undertaker vs. Edge - WrestleMania 24
A critically acclaimed main event for the World Heavyweight Championship, this match reignited a long and intense rivalry. Edge, the reigning champion, pulled out all the stops to end The Streak, but The Undertaker proved resilient. The Phenom reversed a spear into the Hell's Gate submission, forcing Edge to tap out. The victory earned The Undertaker his second World Heavyweight Championship under the "Deadman" persona on SmackDown.
9- The Undertaker vs. The Rock vs. Kurt Angle - Vengeance 2002
This Triple Threat match for the Undisputed WWE Championship featured three of the industry's biggest stars during the his "Big Evil" era. The action was fast-paced and featured incredible chemistry between all three men, particularly Taker and Angle. In a surprising finish, The Rock pinned The Undertaker to capture the Undisputed Championship, marking a notable, non-WrestleMania title loss for The Phenom.
8- The Undertaker vs. Triple H - WrestleMania 27 (No Holds Barred)
A raw, violent slugfest that saw Triple H unleash an aggressive assault with chairs and sledgehammers. The drama centered on The Undertaker's struggle to survive, particularly after three destructive Pedigrees and a Tombstone Piledriver. The Undertaker won via submission with the Hell's Gate, but the toll was so severe he had to be stretchered out, planting the seeds for their "End of an Era" rematch at Mania 28.
7- The Undertaker vs. Brock Lesnar- SummerSlam 2015
This was a brutal rematch fueled by revenge after Lesnar ended Taker's 21-0 streak at WrestleMania 30. The hard-hitting affair saw both men kick out of multiple finishers, including the F5 and Tombstone Piledriver. The controversial finish occurred when Undertaker seemingly tapped out to the Kimura lock, but the referee missed it. Confusion ensued when the timekeeper rang the bell. Capitalizing on the distraction, Undertaker delivered a low blow and locked in the Hell's Gate, causing Lesnar to pass out and giving Undertaker a tainted victory.
6- The Undertaker vs. Mankind - King of the Ring 1998 (Hell in a Cell)
This infamous Hell in a Cell match is iconic for its shocking and brutal violence, forever etching Mick Foley (Mankind) into wrestling lore. Foley took two terrifying falls—first from the top of the 16-foot cell onto the announce table, and then through the top of the cage onto the ring mat. The match was a spectacle of human endurance and brutality, defining the Attitude Era's extreme nature and solidifying The Undertaker's reputation as the Lord of Darkness.
5- The Undertaker vs. Shawn Michaels - Badd Blood 1997 (First Hell in a Cell)
This historic match introduced the Hell in a Cell structure to WWE, a cage designed to keep competitors in and everyone else out. The battle between the two rivals was a vicious affair, setting the template for all future Cell matches. The dramatic conclusion saw the shocking, much-anticipated debut of Kane, who tore the cell door off and delivered a Tombstone Piledriver to his "brother," costing Taker the victory.
4- The Undertaker vs. Shawn Michaels - WrestleMania 26 (Streak vs. Career)
The rematch saw the high stakes of 17-0 The Streak colliding with Michaels' career, adding unmatched emotional intensity. HBK, desperate to defeat The Undertaker, was relentlessly aggressive, yet The Phenom withstood everything. The storytelling was phenomenal, culminating in a defiant Michaels slapping The Undertaker before absorbing the final Tombstone Piledriver. Taker's victory meant Michaels' retirement, marking a poignant and perfect end to HBK's legendary in-ring career.
3- The Undertaker vs. CM Punk - WrestleMania 29
This match is often cited as the last true classic of The Streak era. The storyline was controversial, focusing on CM Punk disrespecting the memory of The Undertaker's manager, Paul Bearer. The contest itself was a technical marvel and a masterclass in in-ring storytelling, with Punk matching Taker move for move. The Phenom overcame Punk’s heel tactics and a barrage of near-falls to secure his 21st victory at WrestleMania.
2- The Undertaker vs. Triple H - WrestleMania 28 (Hell in a Cell)
Dubbed the "End of an Era," this brutal Hell in a Cell match featured Shawn Michaels as the special guest referee, completing the iconic trilogy. The violence and drama inside the cell were immense, with Triple H and Michaels repeatedly using sledgehammers and Sweet Chin Music to try and break The Streak. The emotional climax came when the three legends embraced on the ramp after the match, signaling the final chapter for this generation of stars.
1- The Undertaker vs. Shawn Michaels - WrestleMania 25
This is widely regarded as one of the greatest matches in WWE history. The epic encounter was a true classic, featuring incredible near-falls and high-octane drama that captivated the audience. Michaels, aiming to break The Streak, met The Phenom in a legendary back-and-forth battle. The match elevated The Streak's mystique and set an impossibly high standard, solidifying its place as a quintessential WrestleMania moment when HBK kicked out of the Tombstone. The Undertaker ultimately won, improving his record to 17-0.
