Nobody has entered Hell in a Cell more times than The Undertaker, who has competed in 12 Hell in a Cell matches in his legendary WWE career. Let’s take a look back at them all before his 13th encounter inside the cell with “The Beast” Brock Lesnar.
How destructive are Hell in a Cell matches? The first Hell in a Cell match took place in 1997 for a shot at the WWF Championship between WWE Hall of Famer Shawn Michaels and The Undertaker. Since that hellacious match, there have been only 17 televised Hell in a Cell matches (not including the pay-per-view’s 12 matches since 2009).
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All in all, they’re have been just 30 Hell in a Cell matches in 18 years for WWE. The Undetaker has competed in 12(!) of those 30 matches, winning six of them. Nobody defines the Hell in a Cell match like The Undertaker. Only Triple H (six wins in nine appearances) can match The Phenom’s six victories inside “Satan’s Playground”.
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Oct. 25 will mark the 13th time that The Undertaker will set foot inside Hell in a Cell. The Hell in a Cell pay-per-view will also mark the second time The Deadman has gone one-on-one with Brock Lesnar inside Hell in a Cell. Their first encounter 13 years ago is still talked about to this day and will go down as one of the most intense and physical matches of the last decade and a half.
With that being said, let’s take a match-by-match look at The Undertaker’s long and demonic history inside Hell in a Cell, starting with the match that redefined violence in WWE.
Next: The Undertaker vs. Shawn Michaels, Badd Blood, October 5, 1997
Photo Credit: WWE.com
The Undertaker vs. Shawn Michaels, 1997
If you’re a WWE fanatic, you know this match like the back of your hand.
For the first time, The Undertaker entered Hell in a Cell against the superstar of the 1990s in professional wrestling: “The Heartbreak Kid” Shawn Michaels. The two combatants beat the hell out of each other (no pun intended) for almost a half-hour, and yet, that wasn’t even the biggest takeaway from this match.
Kane made his debut and not only costed The Undertaker a shot at the WWF Championship, he ripped the cell’s door of its hinges and hit his brother’s famous Tombstone Piledriver on The Undertaker himself.
The match itself redefined the business heading into a new era and planted the seeds for the year-long rivalry between Kane and The Undertaker, some of which revolved around the WWF Championship.
Next: The Undertaker and Stone Cold Steve Austin vs. Mankind and Kane, Raw is War, June 15, 1998
Photo Credit: WWE.com
The Undertaker and Stone Cold Steve Austin vs. Mankind and Kane, 1998
There have only been two televised Hell in a Cell matches that didn’t take place at a pay-per-view. The first one was also the first time we saw a tag-team encounter inside Hell in a Cell.
Bam Smack Pow
13 days before the 1998 King of the Ring pay-per-view, four of the biggest stars in the Attitude Era tried to rip each other to shreds, as The Undertaker continued his intense rivalry with Kane (along with Mankind’s intrusion), while WWF Champion Stone Cold Steve Austin had a score to settle with Kane, as The Big Red Machine was the No. 1 contender to Austin’s title.
If you want to call this a match, go right ahead. This encounter was more of an all-out war between the four. Even casual wrestling fans remember this encounter.
Wrestling was reaching new heights in terms of its audience in the later 1990s (thanks to the “Monday Night War”), and this main event of Raw is War became must-see-television as Austin and The Undertaker were challenged to a tag-team match by Mankind and Kane via Paul Bearer.
This match has literally everything: Action inside the cell, outside the cell, on top of the cell, chairs, stairs, and even Paul Bearer being busted open thanks to The Undertaker’s surprise arrival into the brawl.
Next: The Undertaker vs. Mankind, King of the Ring, June 28, 1998
The Undertaker vs. Mankind, 1998
In terms of the most memorable moments in WWE history, Mankind’s plunge off of the cell thanks to The Undertaker might be on top of the list. (And yet, there’s more from this match then just that.)
Mick Foley suffered a concussion, a separated shoulder, a broken jaw, and a tooth was lodged through his upper lip. Not only did Foley take the famous dive off the cell, The Undertaker (performing on a broken foot) chokeslammed him through the top of the cell.
If you’re a wrestling fan of the past or present, you remember this match. How could anyone forget it? There have been some gruesome matches in WWE history, but not many — if any — top this encounter.
Everything about this match was unforgettable. From the viscous bumps Foley took, to the play-by-play calls from Jim Ross and Jerry “The King” Lawler, this match might be the most diabolical of the 30 Hell in a Cell matches in its 18-year history.
Personally, I’ve seen this match at least six times, and every time I watch it, the last thing I ask myself is, “How in the hell did Mick Foley stay alive?” Foley was already a hardcore legend at the time, but this match stapled him as one of the craziest (and toughest) wrestlers that has ever set foot inside the squared circle.
Next: The Undertaker vs. Big Boss Man, WrestleMania XV, March 28, 1999
Photo Credit: YouTube.com
The Undertaker vs. Big Boss Man, 1999
It’s definitely not the most infamous match in WWE history, but this match might have had the most infamous post-match antics in history.
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The Undertaker and his Ministry were at war with Vince McMahon and The Corporation over control of WWF. The Deadman craved more power, and as much as McMahon fought back, The Undertaker was simply a force. So, to settle the score, McMahon threw his henchman, the Big Boss Man, inside Hell in a Cell against The Phenom at WrestleMania XV.
Big mistake, Vince.
Not only did The Undertaker defeat Big Boss Man, thanks to a little assistance from The Brood, The Deadman hung Big Boss Man from the cell after the match. No, seriously … that actually happened.
As Big Boss Man hung from the lifted cell (thanks to Paul Bearer controlling the cell’s height at ringside), Michael Cole’s famous, “Is it symbolic, King?!” was just the icing on the cake on one of the more forgettable (yet memorable) moments in WrestleMania history.
Next: The Undertaker vs. Kurt Angle vs. The Rock vs. Stone Cold Steve Austin vs. Triple H vs. Rikishi, Armageddon, December 10, 2000
The Undertaker against five other stars in Hell in a Cell, 2000
The Hell in a Cell match from the Armageddon pay-per-view in 2000 may not have been the best Hell in a Cell match of all-time, but the star power is still unmatched to this day.
WWF Champion Kurt Angle was set to defend the title inside Hell in a Cell against Stone Cold Steve Austin, The Rock, Triple H, Rikishi and The Undertaker. Simply put, holy crap.
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Outside of a Royal Rumble match, you’ll be hard-pressed to find a match with that many big names. Two names have already been inducted into the WWE Hall of Fame (Austin and Rikishi), while Rock, Triple and The Undertaker are all first-ballot hall of famers. Realistically, even Angle has a legitimate shot at making the WWE Hall of Fame someday as the company’s only Olympic gold medalist.
Once again, this match had everything: A truck ripping the cell door of its hinges, slams onto cars near the entrance way, Stone Cold Stunners, and a chokeslam off the cell from The Undertaker.
Angle would somehow retain the gold after the bloody battle royal for the ages, but the match’s peak found The Undertaker right in the thick of it. His chokeslam on Rikishi into the bed of a pickup truck stopped every single person in their tracks, including the other four stars in the match. It was a moment that will live on in WWE lore for a long, long time.
Next: The Undertaker vs. Brock Lesnar, No Mercy, October 20, 2002
Photo Credit: WWE.com
The Undertaker vs. Brock Lesnar for the WWE Championship, 2002
In terms of one-on-one encounters inside Hell in a Cell, The Undertaker’s duel with Brock Lesnar may have been the best in the match’s 18-year life span. Questions will surround how good their second encounter will be inside the cell due to the PG rating and The Undertaker’s health, but their first match was one for the ages.
FanSided MMA
Lesnar was reigning over WWE as the youngest world champion in history and looking as dominant as one could be in his first year of full-time work. The Undertaker was still the baddest guy on the block, so everyone knew when these two would get together at Unforgiven in 2002, it would tear the roof off the place.
The two stars exceeded expectations in their first one-on-one match and the rivalry got so intense, thanks to Lesnar and Paul Heyman bringing The Undertaker’s wife, Sara into the equation, that the rematch would take place inside Hell in a Cell.
For over 27 minutes, Lesnar and The Undertaker beat each other with an inch of the other’s life, along with The Deadman’s forehead being gashed open like few seen before. The match’s conclusion may have gone Lesnar’s way, as The Beast dropped The Deadman with an emphatic F-5 to retain the gold, but The Undertaker took the young upstart to the absolute limit.
If you’ve never seen a Hell in a Cell match, starting with this one wouldn’t be a terrible idea.
Next: The Undertaker vs. Randy Orton, Armageddon, December 18, 2005
Photo Credit: WWE.com
The Undertaker vs. Randy Orton, 2005
2005 was a great year for both Raw and SmackDown, as the 2005 WWE Draft brought big changes, including John Cena moving to Monday Night Raw, while Batista took the World Heavyweight title to SmackDown.
One of the best rivalries of the year for either brand was the feud between The Undertaker and “The Legend Killer” Randy Orton. The two stars battled throughout all of 2005, including a match-of-the-night candidate at WrestleMania 21.
App Trigger
After Orton called for the cavalry and brought his father “Cowboy” Bob Orton into the fray, Orton picked up two victories over The Undertaker, including costing The Deadman a shot at the World Heavyweight title against JBL before SummerSlam.
Not only did the Ortons defeat The Undertaker at No Mercy in a 2-on-1 handicap casket match, the duo set the casket on fire with The Undertaker inside. But, as The Phenom has stated, “You cannot kill what it is already dead.”
After a short hiatus, The Undertaker made his return after Orton was the sole survivor in the Raw vs. SmackDown Survivor Series main event and wrecked anyone in his path on his way towards Orton. The Undertaker claimed that he would “take Orton to hell” in December at the Armageddon pay-per-view.
With no way out, Orton would be no match for The Undertaker inside Hell in a Cell in a brutal and bloody encounter. Through seven appearances in eight years, The Undertaker would rack up three victories, with a no-contest in one, and not being pinned in another.
Next: The Undertaker vs. Batista, Survivor Series, November 18, 2007
Photo Credit: WWE.com
The Undertaker vs. Batista for the World Heavyweight Championship, 2007
2007 brought another almost year-long feud with a former Evolution member for The Undertaker, as “The Animal” Batista and The Deadman would battle over the World Heavyweight Championship for a bulk of the year.
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Back in January, The Undertaker won his first Royal Rumble match from the No. 30 spot and chose to face Batista for the gold at WrestleMania 23. The Phenom would extend his WrestleMania winning streak to 15-0 by defeating Batista to win his first World Heavyweight title.
An injury would bring the feud to a stop for the time being, as The Undertaker would drop the title to Edge on a June episode of SmackDown after defending the title in a steel cage match against Batista, which ended in a draw. Mark Henry was the one that booked to put The Undertaker on the shelf, and The Deadman would return to defeat Henry at Unforgiven in September.
After dispatching Henry, it was back to Batista for The Deadman. Batista would finally get over the hump and defeat The Undertaker at Cyber Sunday in October, but Big Evil got one more crack at the gold at Survivor Series in November inside the cell.
In The Undertaker’s eighth match inside Hell in a Cell, he was on his way to recapturing the gold in another classic, until the returning Edge (disguised as a cameraman at ringside) drilled him with a camera and two chair shots. Batista would retain the title after Edge dragged him on top of The Undertaker.
Next: The Undertaker vs. Edge, SummerSlam, August 17, 2008
Photo Credit: WWE.com
The Undertaker vs. Edge, 2008
It’s funny how things come around in the wrestling business sometimes. After costing The Undertaker the World Heavyweight title almost nine months to the day prior to SummerSlam, Edge found himself inside Hell in a Cell with The Phenom himself after an entertaining feud throughout the first half of 2008.
The Undertaker won a No. 1 Contender’s match at No Way Out inside the Elimination Chamber to get a World Heavyweight title shot at WrestleMania XXIV against Edge. “The Streak” was extended to 16-0 after The Deadman locked in Hell’s Gate on Edge in the main event of the night. SmackDown general manager Vickie Guerrero would go on to ban the submission hold, leading to Edge regaining the title later on at One Night Stand in a TLC match.
After a … “mishap” by Edge, leading to a separation from Vickie Guerrero, SmackDown’s GM reinstated The Undertaker after he was “banished” for his One Night Stand loss, and threw her former lover inside Hell in a Cell against The Deadman.
In the second of three straight Hell in a Cell appearances for The Undertaker from 2007-09, The Deadman exacted sweet revenge on The Rated-R Superstar with a victory inside the cell.
Not only did The Undertaker get his vengeance for missing out on regaining the World Heavyweight title, he got payback for Edge costing him the title earlier in the year thanks to La Familia, and sent Edge straight to hell.
Next: The Undertaker vs. CM Punk, October 4, 2009, Hell in a Cell PPV
Photo Credit: WWE.com
The Undertaker vs. CM Punk for the World Heavyweight Championship, 2009
Let’s face facts: You couldn’t create a Hell in a Cell pay-per-view without The Undertaker’s involvement.
In the inaugural Hell in a Cell pay-per-view, The Undertaker would take on CM Punk for the World Heavyweight Championship. The Deadman took some time off throughout the early part of 2009 and returned with a bang at SummerSlam. After CM Punk was finally able to rid himself of Jeff Hardy, his next contender came calling right away.
In yet another “Holy crap, it’s The Undertaker!” moment, The Deadman set his sights on the World Heavyweight title once again. The two would meet at Breaking Point afterwards, leading to another version of the “Montreal Screwjob”, helping Punk retain the gold in a submission match.
The Undertaker would get his rematch, and it would come in what was seen as his home: A Hell in a Cell match. For the first time inside Hell in a Cell, a title would change hands, and The Undertaker would become a three-time World Heavyweight Champion.
The Deadman’s next encounter inside the cell (his 11th) would come almost a year to the day after winning back the gold, and this time, not only would it for the gold, it would come against a familiar opponent.
Next: The Undertaker vs. Kane, Hell in a Cell PPV, October 3, 2010
The Undertaker vs. Kane for the World Heavyweight Championship, 2010
In terms of nostalgia, I don’t know if there’s a Hell in a Cell match that had more than the match between The Undertaker and Kane for the World Heavyweight Championship at the 2010 Hell in a Cell pay-per-view.
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The world was introduced to Kane 14 years prior in a Hell in a Cell match involving The Undertaker, and in their 2010 encounter, Paul Bearer would make the difference once again.
A year after making a triumphant return at SummerSlam, The Undertaker would return once again during “The Biggest Party of the Summer” to confront Kane and Rey Mysterio after their title match. But, it would be Kane that would come out on top of their encounter.
At Night of Champions, Kane would get the upper hand on his big brother once again by defeating him for the gold. The Undertaker would continue to search for answers to top his younger brother, and the answer came in the form of the Father of Destruction. Paul Bearer would return in a casket nine days before the Kane-Undertaker rematch at Hell in a Cell, and it appeared that The Deadman was on his way to title reign No. 4.
But, after a brutal 20-minute showdown inside the cell, Paul Bearer would turn on The Undertaker with the famous urn and give Kane another victory over his brother. The Brothers of Destruction would get it on one more time at Bragging Rights in a Buried Alive match, but their encounter inside the cell was the lasting memory of the feud.
Next: The Undertaker vs. Triple H, WrestleMania XXVIII, April 1, 2012
The Undertaker vs. Triple H, 2012
In wrestling, there are matches that come along and for 20, 30, 40 minutes, and you find yourself glued to the television screen for every second of them. The final encounter between The Undertaker and Triple H at WrestleMania XXVIII was one of those matches.
In a four-year span from 2009-12, The Undertaker’s toughest tests to date at WrestleMania, all came from either Shawn Michaels or Triple H. The Deadman retired HBK after their rematch in 2010, but their match in 2009 may have been the greatest match in WrestleMania history. Triple H got his second shot at breaking “The Streak” at WrestleMania XXVII after an unsuccessful try in 2001 and couldn’t get the job done.
So, what was left for The Undertaker? Despite The Game dropping to 0-2 at WrestleMania a year prior, he was the one who actually walked out of the ring that night in Atlanta.
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The Game wanted one more crack at breaking the greatest streak in sports entertainment. The last two pieces of the Attitude Era would duke it out one more time inside Hell in a Cell. Not only would the greatest era in wrestling be coming to an official close, the man who helped led the company into that era — Shawn Michaels — would be given the task of counting the pinfall for this rematch.
For 31 minutes, we all witnessed a fitting end to an era. This match had brutality, physicality, emotion, pain, and told quite a story. Despite a glance into a time machine with a Sweet Chin Music-Pedigree combo that brought the nearest of pinfalls, The Undertaker would leave Miami with his unbeaten streak intact.
The three cornerstones of the company did it the right way and left the stadium together arm-in-arm. There would be a lot of arguing and a lot of discussions to be had, but if a “Mount Rushmore” was made for WWE, these three men would probably find themselves on it.
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