The Undertaker's history in Hell

The Undertaker has a long and storied history inside Hell in a Cell — a match he helped revolutionize along with Shawn Michaels at Bad Blood 1997. At WrestleMania XXVIII, The Deadman will once again enter Hell in a Cell with HBK, but The Showstopper will instead be the special referee. The Phenom’s opponent will be another Superstar as familiar with the treacherous structure as himself and HBK, Triple H. Before his epic clash with The Game, WWE.com takes a look back at The Undertaker’s history inside The Devil’s Playground.

Undertaker vs. Shawn Michaels — In Your House: Bad Blood, Oct. 5, 1997

If the first-ever Hell in a Cell Match pitting Shawn Michaels against The Undertaker proved anything, it was that Satan’s Structure is one of the most demonic and treacherous contraptions ever devised. The brutal contest showed the WWE Universe that Hell in a Cell was much more than an amped up version of a steel cage — the entire environment was a dangerous weapon.

An unfortunate cameraman was caught in the path of Michaels and The Deadman and injured, allowing the two Superstars to take the battle outside and on top of the Cell. The physicality of the contest was highlighted when HBK fell from the side of the cage and through an announce table.

Although it seemed as though The Phenom was truly in his element and would claim victory after mercilessly battling HBK, his plans were derailed when Kane made his fiery debut, ripped off the Cell door and Tombstoned The Deadman, allowing Michaels to pick up the victory.

Undertaker & “Stone Cold” Steve Austin vs. Kane & Mankind — Raw, June 15, 1998

The Undertaker was part of the second Hell in a Cell Match in WWE history in the summer of 1998. However, this contest was the first and thus far only traditional tag team match to take place inside The Devil’s Playground. But the match did not go down as planned as total chaos ensued amongst the four combustible elements involved. Adding to the unpredictably of the evening, Paul Bearer, who had betrayed The Undertaker, accompanied Kane & Mankind to the ring.

After everyone but The Phenom made their entrances, Paul Bearer locked himself inside Satan’s Structure to protect himself from The Deadman, and ordered Kane & Makind to attack Austin. But Bearer’s plan was for naught as The Demon from Death Valley made his way through the ring and brutally attacked his former manager while Kane and Mankind helplessly watched.

Undertaker vs. Mankind — King of the Ring, June 28, 1998

The most infamous and defining Hell in a Cell Match not only set a precedent for all future battles inside The Devil’s Playground, but it also solidified The Undertaker as one of the most dominating forces in WWE history, and proved beyond a shadow of a doubt that Mick Foley was indeed The Hardcore Legend.

This particular Hell in a Cell Match began on top of the cell. As the two legends traded blows and chair shots at this precarious height, the most iconic moment in any Hell in a Cell Match occurred. Only two minutes into the contest, The Phenom threw Mankind from the top of the cell and through the announce table below.

Amazingly, Mankind kept on fighting, avoiding medical attention and climbing back to the roof of the structure. The Undertaker met his nemesis there and chokeslammed him through the cell and into the ring. Mankind continued to mount an offense and even gained some momentum before being dropped on top of a pile of thumbtacks. The epic clash finally ended with a Tombstone and The Undertaker securing the win.

Undertaker vs. Big Boss Man — WrestleMania XV, March 28, 1999

The only other Hell in a Cell Match at WrestleMania occurred in 1999 when The Undertaker squared off with The Big Boss Man. At the time, The Phenom was trying to instill a reign of darkness over WWE as the leader of the sinister Ministry. He set his sights on Mr. McMahon and The Corporation, thus crossing paths with the faction’s head of security, The Big Boss Man.

As expected from any Hell in a Cell contest, the match was intensely physical with weapons being used by both Superstars inside The Devil’s Playground. It seemed as though Big Boss Man was a formidable opponent for The Deadman and could have potentially ended The Streak at 7-0, but The Undertaker proved his resilience and defeated the tough Superstar, keeping The Streak intact.

Undertaker vs. Kurt Angle vs. “Stone Cold” Steve Austin vs. Triple H vs. Rikishi vs. The Rock — Armageddon, Dec. 10, 2000

The Undertaker and Triple H have both been involved in a lion’s share of Hell in a Cell matches. Thus, it is no surprise that WrestleMania XXVIII will not be the first time both Superstars have been inside Satan’s Structure against one another. However, there were also four other Superstars in the contest vying for Kurt Angle’s WWE Championship.

Bedlam and chaos are the only two words that can really describe what took place in this contest. Any one of the Superstars in the battle could have become the WWE Champion with a pinfall or submission, but it would take an all-out brawl on top of the cage, Undertaker throwing Rikishi from the roof and an epic clash inside the ring between The Rock, “Stone Cold” Steve Austin, Triple H and Kurt Angle before Angle barely pinned The Rock to retain the WWE Title.

Although neither The Deadman nor Triple H were successful or pinned, this battle proved the resilience of both Superstars inside Satan’s Structure.

Undertaker vs. Brock Lesnar — No Mercy, Oct. 20, 2002

The Undertaker’s first true defeat inside Hell in a Cell came at the hands of then-WWE Champion Brock Lesnar. Under the guidance of Paul Heyman, Lesnar came roaring into WWE like an F-5 tornado and it wasn’t long until he squared off with The Deadman. When the two Superstars collided inside Hell in a Cell, it was the perfect clash between the seasoned veteran and the young powerhouse.

Throughout the entire battle, neither Superstar maintained a solid wave of momentum for very long. The Phenom would counter Lesnar with experience and Lesnar would counter with pure strength. Adding in the variables that come with Hell in a Cell, the WWE Universe witnessed one of the most physically demanding challenges in either Superstar’s respective careers. The steel steps, the unforgiving steel cage and distraction from Paul Heyman did not keep The Undertaker at bay, but Lesnar’s brute strength in reversing a Tombstone proved to be too much for The Deadman after the vicious battle.

Undertaker vs. Randy Orton — Armageddon, Dec. 18, 2005

After failing to defeat The Undertaker at WrestleMania 21, Randy Orton, then known as “The Legend Killer,” made it his personal goal to put an end to The Deadman. Throughout the remainder of 2005, The Viper even enlisted the help of his father, WWE Hall of Famer “Cowboy” Bob Orton. The father and son duo defeated Undertaker at SummerSlam 2005 and in a Casket Match at No Mercy. With a desire to end Orton’s reign once and for all, the final battle between The Deadman and The Viper occurred inside The Devil’s Playground.

Once again, The Undertaker found himself embroiled in a physical and personal battle. Inside Satan’s Structure, The Viper and The Deadman used the steel steps and even brought a table into the ring in an attempt to end their rivalry. But the rage of The Demon from Death Valley was too much for Orton, and even attempted interference from “Cowboy” Bob was unsuccessful. In the end, The Undertaker got the best of the Orton family by Tombstoning both father and son.

Undertaker vs. Batista — Survivor Series, Nov. 18, 2007

Batista and The Undertaker shared a number of memorable matches in late 2006 and throughout 2007. The Animal nearly ended The Streak at WrestleMania 23, and the World Heavyweight Championship would become the focal point of their rivalry. However, perhaps none of their battles were as memorable as the one that took place inside Hell in a Cell.

Both Superstars seemed to have an edge at different points in the bout and each had their share of dominate moments. At one point in the battle, The Animal put The Undertaker through a table with a powerful Batista Bomb. Not staying down for long, The Deadman countered by hitting Batista with the Tombstone on top of the steel steps. It’s possible the match could have gone all night, but Edge, disguised as a WWE cameraman, attacked The Undertaker and dragged Batista on top of The Phenom for a tainted finish.

Undertaker vs. Edge — SummerSlam , Aug. 17, 2008

Edge’s attack at Survivor Series 2007 was only the beginning of a budding rivalry between The Deadman and The Rated-R Superstar. The Undertaker defeated Edge for the World Heavyweight Title at WrestleMania XXIV, but they continued to battle each other throughout 2008 and would meet inside Satan’s Structure at SummerSlam.

The Undertaker had been in numerous physical and grueling battles inside The Devil’s Playground before, but Edge brought a unique trait to the squared circle. The Rated-R Superstar was one of the innovators of the Tables, Ladders and Chairs Match in which he also defeated The Phenom. Almost immediately, Edge took control of the match and utilized all three of his trademark weapons. However, The Undertaker was used to the punishment that comes inside Hell in a Cell and managed to defeat Edge.

After the match, as he walked away from the ring, The Deadman noticed Edge was still moving. He returned to the ring and chokeslammed The Rated-R Superstar off a ladder and through the ring canvas.

Undertaker vs. CM Punk — Hell in a Cell, Oct. 4, 2009

By 2009, the Hell in a Cell Match had become so prominent that an entire event was created to feature a handful of battles inside The Devil’s Playground. It was only fitting for The Deadman to open the event inside Satan’s Structure against then-World Heavyweight Champion CM Punk.

This was The Straight Edge Superstar’s first foray into Hell in a Cell and The Undertaker’s tenth. The odds were clearly stacked against Punk, but he still tried to mount an offense by attacking The Undertaker’s legs. However, experience proved to be the key in this contest as The Phenom defeated The Straight Edge Superstar to win the World Heavyweight Title. This victory also marked the first time that a championship changed hands inside The Devil’s Playground.

Undertaker vs. Kane — Hell in a Cell, Oct. 3, 2010

In the 13 years since Kane debuted by attacking The Phenom inside Hell in a Cell, The Big Red Monster has never squared off with The Undertaker in The Devil’s Playground. That changed in 2010 when The Brothers of Destruction entered Satan’s Structure to battle for the World Heavyweight Title.

Leading up to the contest, The Undertaker appeared vulnerable, having seemingly lost some of his mythical powers. However, a returning Paul Bearer restored The Deadman’s abilities and it seemed as though Kane would meet certain demise inside Hell in a Cell. The battle was strongly reminiscent of their epic clashes throughout the late-1990s and into the early-2000s. However, it was a final betrayal at the hands of Paul Bearer that would cost The Undertaker the victory.

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