Here is Undertaker's History in hell In a Cell:

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.

As his lengthy rivalry with Mankind (Mick Foley) intensified, Undertaker prepared to meet Foley inside the Cell. After an early-June 1998 Cell battle pitting Undertaker & Stone Cold vs. Mankind & Kane was ruled a No Contest, The Phenom was still hungry for his first victory inside the structure.
In quite possibly the most widely-replayed moment in WWE history, Undertaker tossed Foley off the top of the Cell. Mankind's body hurtled over 20 feet, finally crashing back to terra firma in the form of the announcers’ table. Foley somehow then scrambled back to the top of the Cell, where Undertaker chokeslammed him through the roof, sending poor Mankind crashing 15 feet to the mat below. Mercifully, the match ended minutes later following a Tombstone.

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.
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R.I.P.