There have been 15 Hell in a Cell Matches, and as it stands, Undertaker has the most appearances inside the Cell with eight - a fitting amount of trips to Hell for the Superstar known as The Deadman. No one knows firsthand the dangers of the unfriendly confines better than Undertaker; that said, while he may be 15-0 on WWE’s biggest stage of WrestleMania and a five-time World Champion, The Phenom is only 3-4-1 inside the Cell.
With their 2007 rivalry tied at one win apiece with two draws, Undertaker and Batista stepped inside the Cell at Survivor Series to battle for the World Heavyweight Championship.
Just when it looked like The Phenom had the champion beat, Edge made a shocking return after a four-month absence. Thanks to a little chicanery - and a well-placed chair to the head - from the Rated-R Superstar, Undertaker was incapacitated. Edge then dragged The Animal on top of The Phenom for the winning pinfall.
To conclude a rivalry that lasted nearly all of 2005, The Deadman returned to Hell in a Cell at Armageddon against Randy Orton. With both men pretty much even in wins, it was finally to be settled inside the Cell.
That night, Undertaker put to bed the notion of the Legend Killer destroying his legacy once and for all. Randy’s father, WWE Hall of Famer “Cowboy” Bob Orton even got involved, but that didn’t matter to The Deadman. After battering and bloodying Randy – and busting Bob open as well – Undertaker finally put a seal on their rivalry by dropping the Legend Killer with a vicious Tombstone for the pinfall. Following the bout, The Phenom climbed up onto the Cell roof and dropped to one knee, posing for the capacity crowd while bathed in an eerie purple light.
After a near two-year absence, Undertaker returned to the Cell sporting a 2-2-1 record at No Mercy 2002. This time, Hell in a Cell meant facing Brock Lesnar for the WWE Championship.
Unfortunately, The Phenom left Little Rock, Ark., that night with both an empty waist and a losing Cell record. Despite battling Lesnar tooth-and-nail in another bloody, brutal battle, The Deadman came up just short. In an impressive strength display, Lesnar reversed a Tombstone attempt into his own F-5 Signature move, using that to pin Undertaker and retain the WWE Championship.
Armageddon 2000 saw the first Hell in a Cell Match featuring more than four combatants, as six men piled into the structure to do battle over the WWE Championship. Undertaker wasn't victorious in the bout – then-champion Kurt Angle retained the title – but The Deadman was responsible for another classic Hell in a Cell moment.
As The Phenom battled Rikishi on the Cell roof, flashbacks of poor Mick Foley ran through the minds of many. Those were validated just minutes later, as Undertaker hoisted the 300-plus pound Samoan in the air, chokeslamming him down off the roof and into the bed of a Mr. McMahon-driven pickup truck parked nearly 20 feet below.
In 1999, faction warfare between Undertaker's Ministry of Darkness and The McMahons' Corporation reached its brutal peak on WWE's grandest stage when Mr. McMahon sent his trusty head of security, Big Boss Man, inside Hell in a Cell at WrestleMania XV to battle The Deadman.
There could only be sweet Philadelphia freedom for one combtatant, and unfortunately for Boss Man, he found out that the saying "Don't Cross the Boss" didn't just apply to his own leader. After brutalizing Boss Man and introducing him into the Cell the hard way, Undertaker finished him off with a vicious Tombstone Piledriver, and Ministry members Gangrel, Edge & Christian – rappeled from the ceiling to take the fallen former Prison Guard as a token sacrifice.
Watch video of the match | Match Photos
The Deadman was part of the first Hell in a Cell Battle, as his rivalry with Shawn Michaels – who had cost him the WWE Title at SummerSlam 1997 – led to the structure’s inaugural appearance. On Oct. 5, 1997, our fans witnessed first-hand the devastation that can occur inside the Cell; for over half an hour, Undertaker battered Shawn Michaels to within an inch of his career, bloodying HBK like never before. However, Badd Blood wasn’t just the first appearance of Hell in a Cell; it was also the first appearance of Kane. And thanks to a timely Tombstone from Undertaker’s baby brother, Michaels somehow escaped the brutal beating with a pinfall victory.