The Undertaker is one of the best performers of all time inside Hell in a Cell. The Phenom has taken this match to the next level. The Phenom is synonymous with the casket and buried alive match but has molded the Hell in a Cell into another one of his specialty matches.
No man in WWE history has participated in more Hell in a Cell matches than The Undertaker. He has the most wins with eight but has suffered six losses in Satan's structure.
10 Six-Man Hell In a Cell - Armageddon 2000
In 2000, The Undertaker ditched his Deadman persona for his American Badass gimmick. At Armageddon, Undertaker debuted Limp Bizkit's Rollin' as his new theme song. Taker participated in the first-ever (and only to date) six-man Hell in a Cell Match for the WWF Championship.
Kurt Angle defended his title against Taker, The Rock, Stone Cold Steve Austin, Triple H, and Rikishi. That is a Hall of Fame cast but the most memorable moment in this classic Hell in a Cell match was Taker throwing Rikishi off the top of the cell. That was the high note for Taker as he came up short in his quest to be WWF Champion once more with Angle running out the victor.
9 Undertaker Vs Shane McMahon - WrestleMania 32
Shane McMahon made his return to the WWE for the first time in six years in early 2016. The Boy Wonder's celebration was short-lived as he was put in a Hell in a Cell match against The Undertaker at WrestleMania 32 by his father Mr.McMahon.
There was another stipulation added to this match, had Shane defeated Taker, The Phenom would no longer compete at future WrestleMania events. McMahon missed his Leap of Faith off the top of the cell with Taker prone on the announce table. Taker would Tombstone McMahon preserving his status to compete at future WrestleManias.
8 Undertaker Vs Batista - Survivor Series 2007
In 2007, Batista and The Undertaker had the rivalry of the year over on Smackdown for the World Heavyweight Championship. Taker would win their encounter at WrestleMania 23 with Batista returning the favor at Cyber Sunday.
The Hell in a Cell Match for the World Heavyweight Championship at Survivor Series 2007 was the decider. The Deadman was closing in on another World Title with a Tombstone to Batista on the steel steps. However, Edge (disguised as a cameraman) interfered, nailing Taker with a steel chair, and placing Batista onto Taker to retain the title.
7 Undertaker Vs Brock Lesnar - Hell In A Cell 2015
At Hell in a Cell 2015, The Undertaker and Brock Lesnar faced off for the last time in Satan's structure. Lesnar famously ended Taker's unbeaten WrestleMania streak at WrestleMania 30. However, the Phenom would cost Lesnar a WWE Championship match at Battleground in July 2015.
Taker would beat the Beast Incarnate at SummerSlam. Their match at Hell in a Cell was physical and bloody. The mat was exposed with Taker executing a Tombstone to Lesnar who managed to kick out but Lesnar won the match with his third F-5 and The Wyatt Family would attack The Undertaker, carrying him away.
6 Undertaker Vs Edge - SummerSlam 2008
The Undertaker and Edge dominated their rivalry on Smackdown in 2008 over the World Heavyweight Championship. The pair traded the title between themselves with Taker being banished from the WWE at One Night Stand in 2008 in a TLC match against Edge.
However, Vickie Guerrero reinstated Taker as Edge finally got his comeuppance for his infidelity on Vickie with Alicia Fox, their supposed wedding planner. The two squared off in an entertaining Hell in a Cell match at SummerSlam. Taker tombstoned the Rated-R Superstar for the victory. Taker was not done there as he chokeslammed Edge straight to hell, through the ring with flames lighting up.
5 Undertaker Vs Randy Orton - Armageddon 2005
The Undertaker's 2005 rivalry with Randy Orton made the Legend Killer a star. Orton had the edge over The Deadman with wins at SummerSlam, and in the first-ever Handicap Casket match with his father "Cowboy" Bob at No Mercy. Taker won their first outstanding classic together at WrestleMania 21 to go 13-0.
At Armageddon, The Undertaker and Orton's feud would culminate inside Hell of a Cell. The Deadman took Orton to the woodshed, gaining some revenge in this bloody encounter with Taker tombstoning both "Cowboy" Bob and Randy.
4 Undertaker Vs Brock Lesnar - No Mercy 2002
When the majority of wrestling fans think about Lesnar and Undertaker's history, they think about WrestleMania 30. The two former world champions' rivalry dates back to 2002. Brock Lesnar was the Next Big Thing as he sent The Rock packing to Hollywood at SummerSlam.
Taker and Lesnar would put on an outstanding Hell in a Cell Match for the WWE Championship at No Mercy 2002. The Phenom broke his hand in this WWE Championship bout but continued to pummel Lesnar. The Next Big Thing cemented his spot as the top dog on Smackdown with a clean victory over The Undertaker.
3 Undertaker Vs Triple H - WrestleMania 28
The "End of an Era" Hell in a Cell match at WrestleMania 28 pitted The Undertaker against Triple H. It was the perfect way to end a decade-long rivalry between two of the greatest superstars of all time. It was the third meeting between The Deadman and The Game at WrestleMania. Taker won their encounters at WrestleMania 17 and 27 but Triple H was determined to break the streak.
The winner of the first-ever Hell in a Cell match, Shawn Michaels, was assigned the role as special guest referee. Michaels retired against Taker two years prior in the main event at WrestleMania 26. Taker and Triple H are both synonymous with the Hell in a Cell with the most wins in history.
The Phenom managed to overcome the adversity he faced in this match with the two DX men combining with a Sweet Chin Music and Pedigree. Taker tombstoned Triple H extending his streak to 20-0. The three men had a huge ton of respect for each other, with the three embracing at the top of the ramp.
2 Undertaker Vs Mankind - King Of The Ring 1998
The reason why Mick Foley walks with a limp in his everyday life can be traced back to King of the Ring 1998. Foley wrestling in his Mankind persona was a thorn in The Undertaker's side for two years. Their Hell in a Cell match at King of the Ring is widely spoken about to this day as Mankind took two nasty bumps in this brutal encounter.
The Deadman threw him off the cell onto the announce table. He was not done there, as he climbed back up to get chokeslammed through the cell into the ring in an unplanned spot. Mankind's high threshold of pain was evident that night with Taker putting him out of his misery with a Tombstone Piledriver. The fact that they even finished off this match is a testament to both men's professionalism and toughness.
1 Undertaker Vs Shawn Michaels - Badd Blood: In Your House 1997
The Undertaker's Hell in a Cell match with Mankind may be memorable but the first-ever Hell in a Cell with Shawn Michaels was brilliant. Taker and Michaels locked horns at Badd Blood: In Your House in 1997. HBK accidentally cost The Phenom his WWF Championship at SummerSlam. Michaels would try to run away from Taker but had nowhere to go inside Hell in a Cell.
This match set the bar for future Hell in a Cell clashes in later years. Michaels would suffer a fall off the side of the cell onto the announce table. HBK was a bloody mess as Taker dominated this match. However, in the closing stages, Kane made his WWE debut. It was a picturesque moment with Kane and Undertaker face-to-face for the first time. Kane tombstoned his brother with Michaels' battered body covering Taker, earning the right to face Bret Hart for the WWF Championship at the 1997 Survivor Series.