Few wrestlers in history have left an impact quite like The Undertaker. With a career spanning over three decades, he built a legacy filled with unforgettable moments, intense rivalries, and matches that will be remembered for generations. From WrestleMania classics to brutal Hell in a Cell encounters, The Phenom delivered some of WWE’s greatest performances. His ability to tell a story in the ring, combined with his unmatched presence, made every contest feel special.
Throughout his career, The Undertaker faced some of the industry’s biggest names in battles that pushed the limits of endurance and storytelling. Whether it was against legendary opponents like Shawn Michaels or modern superstars like Brock Lesnar, his matches consistently stood out. Here are four of the greatest matches that defined his legacy and solidified his status as one of the all-time greats.
1. The Undertaker vs. Shawn Michaels – WrestleMania 25 (2009)
Shawn Michaels vs. The Undertaker (Image via Getty)Many fans consider this match the best in WrestleMania history. The Undertaker and Shawn Michaels put on a flawless performance, blending athleticism, emotion, and drama into a masterpiece. The contrast between Michaels’ high-flying style and The Undertaker’s brute strength created an incredible dynamic, keeping the audience on the edge of their seats.
The near-falls were breathtaking, with each competitor refusing to stay down. Michaels came close to victory multiple times, countering The Undertaker’s signature moves with precision. However, after an exhausting battle, a perfectly executed Tombstone Piledriver sealed the win for the Deadman. This match was more than just a contest—it was a showcase of storytelling at its finest, proving why both men are regarded as legends.
2. The Undertaker vs. Mankind – Hell in a Cell (1998)
This brutal encounter remains one of WWE’s most infamous matches. The Undertaker and Mankind took Hell in a Cell to another level, delivering a contest filled with jaw-dropping moments that redefined hardcore wrestling.
The match began with Mankind climbing to the top of the cage, only to be thrown off by The Undertaker in one of the most memorable moments in wrestling history. The fall through the announce table looked devastating, but the punishment didn’t stop there. Mankind later crashed through the cell roof, suffering another terrifying landing. Despite the extreme punishment, he refused to quit, embodying pure resilience.
The Undertaker ultimately secured victory, but this contest was more than just a win. It was a display of endurance, pain, and heart that remains one of the most talked-about matches in WWE history.
3. The Undertaker vs. Triple H – WrestleMania 28 (2012)
Triple H vs. The Undertaker (Image via Getty)Billed as the “End of an Era,” this Hell in a Cell match featured The Undertaker, Triple H, and special referee Shawn Michaels in a battle that felt like the closing chapter of a legendary period in WWE.
The match was a hard-hitting war, with both men delivering punishing offense. Triple H used steel chairs and sledgehammers to weaken The Undertaker, while Michaels added emotional intensity with his torn allegiances. The near counts and dramatic moments had the crowd fully engaged, especially when Michaels hit Sweet Chin Music, nearly ending The Undertaker’s streak.
Despite the relentless assault, The Undertaker found a way to win, hitting the Tombstone for the victory. As he, Triple H, and Michaels walked up the ramp together, it felt like the end of something truly special—a match that symbolized the legacy of three icons.
4. The Undertaker vs. Brock Lesnar – WrestleMania 30 (2014)
This match is remembered for one reason: the end of The Undertaker’s legendary WrestleMania streak. For 21 straight matches, he had walked out victorious, but on this night, Brock Lesnar changed history.
The match itself was a battle of power and resilience. The Undertaker, though older and worn from years of competition, refused to go down easily. He absorbed brutal suplexes and F-5s, showing his legendary toughness. However, Lesnar’s sheer force proved too much. When he delivered a third F-5 and scored the pin, the arena fell into stunned silence.
This moment signified the end of an era in WrestleMania history. Though heartbreaking for fans, it cemented The Undertaker’s legacy as a competitor who always put everything on the line, even in defeat.
The Undertaker’s career is filled with unforgettable moments, and these matches represent just a few of his greatest performances. Whether through brutal wars or technical classics, he created memories that will last a lifetime. His legacy in WWE remains unmatched, and his influence on the industry will be felt for generations.