He made his WrestleMania debut at WrestleMania VII, quickly defeating "Superfly" Jimmy Snuka. He began his first major feud with The Ultimate Warrior, when he attacked the Warrior and locked him in an airtight casket on the set of his manager, Paul Bearer's Funeral Parlor interview segment. After a year of battles with the Warrior, Randy Savage, Sid Justice, Sgt. Slaughter, and Hulk Hogan, he defeated Hogan to win his first WWF Championship at Survivor Series with the help of Ric Flair, and thus became the youngest WWF Champion in history until having this record broken by Yokozuna in 1993. WWF President Jack Tunney ordered a rematch for This Tuesday in Texas six days later, where The Undertaker lost the title back to Hogan.
In February 1992, The Undertaker's ally Jake "The Snake" Roberts tried to attack Randy Savage's manager/wife Miss Elizabeth with a steel chair when The Undertaker stopped him, becoming a fan favorite for the first time. Then, Undertaker defeated Roberts at WrestleMania VIII, continuing his winning streak at the event. He then feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993, such as Kamala, Giant González and Yokozuna. Also in this time he headlined the first episode of Monday Night Raw on January 11, 1993 with a victory over Damien Demento. He faced González at WrestleMania IX, which is notable as Undertaker's only disqualification win at WrestleMania after the use of chloroform. His rivalry with Yokozuna culminated in a WWF Championship casket match at the 1994 Royal Rumble. During the match, champion Yokozuna sealed The Undertaker in the casket with the assistance of several other villainous Wippleman-managed wrestlers to win the match. The Undertaker appeared from inside the casket on the video screen, representing his spirit, warning that he would return. The Undertaker did not appear in the WWF for seven months after his loss to Yokozuna. In reality, he was given time off to allow a back injury to heal.
During his absence, the WWF promoted his return by showing video clips of people who claimed to have seen The Undertaker. After WrestleMania X, Ted DiBiase introduced an Undertaker back to the WWF. This Undertaker, however, played by Chainz, was an impostor Undertaker (dubbed the "Underfaker" by fans) and led to the return of the real Undertaker in the SummerSlam main event, appearing as a new version of his original Deadman persona, replacing grey with purple. The Undertaker defeated the impostor after three Tombstone Piledrivers. At Survivor Series, The Undertaker defeated Yokozuna in a rematch, another casket match. Throughout most of 1995, The Undertaker feuded with members of Ted DiBiase's Million Dollar Corporation. At WrestleMania XI, while Undertaker was facing King Kong Bundy, Kama stole The Undertaker's urn, and antagonized him by melting it into a large gold necklace and attacking the Undertaker. Later, The Undertaker defeated Kama in a casket match at SummerSlam. Several weeks later, The Undertaker injured his orbital bone near his eye, forcing a period of absence for surgery, until his return at Survivor Series.
The Undertaker returned at the 1995 Survivor Series, wearing a Phantom of the Opera-like, grey upper-face mask. In the main event of the 1996 Royal Rumble, The Undertaker was unmasked in a WWF Championship match against Bret Hart, when Diesel interfered in the match to cost the Undertaker the championship. A rematch for the title on the February 5 episode of Raw saw similar interference. At that month's In Your House: Rage in the Cage, while Diesel was facing Hart in a steel cage match, The Undertaker burst through the ring and dragged Diesel underneath which allowed Hart to get the victory. This feud culminated in a match between Diesel and the Undertaker at WrestleMania XII, in which The Undertaker was victorious.
His next feud commenced the very next night, when Mankind made his debut, interfering in The Undertaker's match with Justin Hawk Bradshaw. For the next few months, Mankind ambushed and cost The Undertaker several matches. The feud intensified, and they began taking their battles into crowds, backstage areas, and in the boiler rooms of different arenas. Mankind cost the Undertaker the WWF Intercontinental Championship at In Your House 8: Beware of Dog, assisting champion Goldust to victory. As a result, the first ever Boiler Room Brawl was booked between the two at SummerSlam. During the match, when Undertaker reached for Paul Bearer's urn, Bearer hit him with it, betraying The Undertaker and allowing Mankind to "incapacitate" The Undertaker with the Mandible claw, giving him the win. After Bearer's betrayal, The Undertaker took his rivalry with Mankind to a new level, resulting in a Buried Alive match in the main event of In Your House: Buried Alive. The Undertaker won the match after a chokeslam into the open grave, but after interference from The Executioner, as well as the help of several other superstars, The Undertaker was ultimately "Buried Alive."
After being buried alive, The Undertaker returned at the Survivor Series again pitting him against Mankind, but with a unique stipulation; hanging 20 ft. above the ring was Paul Bearer, enclosed in a steel cage. If Undertaker won the match, he would be able to get his hands on Bearer. Even though The Undertaker won the match, interference from The Executioner enabled Bearer to escape The Undertaker's clutches. With no manager, Undertaker developed a more humanized incarnation, with a different, gothic and rebelling attitude — perhaps to better fit him to The Attitude Era, a more adult-oriented programming content period of World Wrestling Federation —, proclaiming himself to be "The Lord of Darkness". The Undertaker then briefly turned his attention to The Executioner, who had become a thorn in his side since his arrival and had helped bury him alive in the eponymous match. At In Your House: It's Time, The Undertaker defeated The Executioner in an Armageddon rules match. He then moved on to feud with Vader. They met at the 1997 Royal Rumble in a singles match, where Undertaker lost after Bearer interfered on behalf of his new protégé. The two then clashed in the Royal Rumble match itself as they made it to the final moments of the match but both were eliminated by Stone Cold Steve Austin, who had crept back into the match after his elimination was unseen. He met both Vader and Austin in a Four Corners Elimination match for the vacant WWF Championship at In Your House 13: Final Four, but Bret Hart won. However, the following month The Undertaker managed to win the title for the second time and continued his undefeated streak by defeating Sycho Sid at WrestleMania 13.
In May 1997, Paul Bearer attempted to rejoin with The Undertaker, using the ultimatum of revealing The Undertaker's "biggest secret." In storyline, Bearer announced that The Undertaker was an arsonist/murderer, who as a child had burned down the family funeral home business (where he and his family lived and Bearer worked), killing his parents and his younger half-brother. The Undertaker claimed there was no way for Bearer to have that information, but Bearer announced that he was told this by Undertaker's half-brother Kane, who was still alive but horribly burned and scarred. Bearer raised Kane after the fire, having him institutionalized. Now, Kane was waiting for revenge after all these years. In defense, The Undertaker responded that Kane, a pyromaniac, had been the one to set the fire and could not have possibly survived.
Concurrently, Undertaker began a new rivalry at SummerSlam when guest referee Shawn Michaels accidentally hit The Undertaker with a steel chair shot meant for Bret Hart, costing the Undertaker his WWF Championship. After a double count-out draw during Ground Zero: In Your House, Undertaker challenged Michaels to the first Hell in a Cell match at Badd Blood: In Your House. During this match, The Undertaker's storyline half-brother Kane finally made his debut under the control of Paul Bearer, ripping off the door to the cell and giving The Undertaker a Tombstone Piledriver, Undertaker's trademark finisher, allowing Michaels to pin him. As the storyline progressed Kane, through Bearer, challenged The Undertaker, but The Undertaker consistently refused to fight his brother. The Undertaker's final encounter with Michaels was in a casket match at the Royal Rumble. The week before, Kane had seemed to ally with his brother against Michaels' D-Generation X but at the PPV Kane trapped him in the coffin, padlocking the casket lid, and setting it ablaze which again gave Michaels the victory. The Undertaker, however, had disappeared when the casket lid was reopened. After a two month hiatus, The Undertaker returned and defeated Kane at WrestleMania XIV. The two had a rematch, the first ever Inferno match, one month later at Unforgiven: In Your House, which The Undertaker won by setting Kane's right arm on fire.
The Undertaker's feud with Mankind was renewed afterward, and they faced each other in a Hell in a Cell match at King of the Ring. During the match, The Undertaker threw Mankind off the roof of the 16 ft. cell onto the Spanish announce table below, in what was a preplanned move. He later chokeslammed Mankind through the roof of the cell into the ring which legitimately knocked Mankind unconscious. Mankind also used thumbtacks in the match and was backdropped and chokeslammed onto them before Undertaker won the match with his Tombstone Piledriver.
At Fully Loaded, The Undertaker and Stone Cold Steve Austin defeated Kane and Mankind to win the WWF Tag Team Championship. The Undertaker and Austin's reign as tag champions lasted for only two months, as Kane and Mankind regained the titles on an episode of Raw is War. The Undertaker then became the number one contender for the WWF Championship at SummerSlam, now held by Austin. Shortly before SummerSlam, however, The Undertaker revealed that he and Kane were working together as brothers. Despite this revelation, The Undertaker told Kane that he did not want him to interfere in the match with Austin, and even though The Undertaker lost the match, he handed Austin his belt back after the match in a show of respect. In September, the storyline continued, and The Undertaker began to show some villainous characteristics when he and Kane revealed the fact that they were in cahoots to rid Austin of his title for Vince McMahon. At Breakdown: In Your House, The Undertaker and Kane were booked in a Triple Threat match with Austin for his WWF Championship; McMahon stated that the brothers were not allowed to pin each other. The Undertaker and Kane pinned Austin simultaneously after a double chokeslam, so the title was vacated by McMahon. This event led to a match at Judgment Day: In Your House between the two brothers for the title, with Austin as the special guest referee. Near the end of the match, Paul Bearer seemed about to assist Kane by handing him a steel chair to hit The Undertaker with, but as Kane had his back turned, both Bearer and The Undertaker hit Kane with the chair. The Undertaker went for the pin, but Austin refused to count the fall, attacked the Undertaker, and counted out both brothers. Finally, The Undertaker became a villain the next night on Raw is War for the first time in over six years, reconciling with Bearer and claiming that he and Bearer would unleash their Ministry of Darkness on the World Wrestling Federation. As part of this new storyline, he admitted that he had indeed set the fire that killed his parents, for which he had previously blamed Kane.
After Survivor Series, The Undertaker returned his attention back to his previous feud with Austin for costing him the title at Judgment Day, hitting Austin in the head with a shovel during a title match with The Rock, returning the favor for what happened a month earlier. With this twist in the storyline, McMahon scheduled a Buried Alive match between The Undertaker and Austin at Rock Bottom: In Your House. In the weeks leading up to Rock Bottom, The Undertaker attempted to embalm Austin alive, tried to have Kane committed to a mental asylum, and had his druids chain Austin to his symbol, raising it high into the arena. The Undertaker, however, lost the match after Kane interfered.
After building up to his second heel run in the latter part of 1998, The Undertaker introduced an updated version of his Deadman identity by January 1999—the dark priest who in the initial period of this persona reigned over a stable known as the "Ministry of Darkness." In this form, he took on a wicked, Satanic presence, much more so than ever before. He often claimed to be invoking and taking orders from a "Higher Power." Moreover, he often appeared in a hooded black robe and sat on a throne that was specially designed into his character symbol. With the help of his minions, he often performed sacrifices on select WWE superstars, using various incantations and magic words with intent to extract out the dark side of the superstars in question so as to recruit them into his Ministry. The completed "Ministry of Darkness" consisted of The Brood (Edge, Christian and Gangrel); The Acolytes (Bradshaw and Faarooq); Mideon; and Viscera. As part of the angle, Undertaker expressed a desire to rid the World Wrestling Federation of its owner, Vince McMahon, and take control of the company. These ambitions culminated into a rivalry between The Ministry and The Corporation, ultimately resulting in a match between Undertaker and Corporation enforcer the Big Boss Man. The two faced off in a Hell in a Cell at WrestleMania XV, which Undertaker won to extend his streak to 8-0. At Backlash, Undertaker defeated an another Corporation member Ken Shamrock after interference from Ministry member Bradshaw.
Thereafter, The Undertaker kidnapped Stephanie McMahon, forcing Vince McMahon to enter into a reluctant alliance with his longtime nemesis Stone Cold Steve Austin. The Undertaker attempted to marry Stephanie in an eldritch ceremony conducted by Paul Bearer, but Austin was able to rescue her. At the Over the Edge pay-per-view, The Undertaker defeated Austin for his third WWF Championship with help from Shane McMahon, the special referee. The Undertaker later revealed that Vince McMahon had been his "Higher Power" all along. The Ministry eventually merged with The Corporation alliance to form the Corporate Ministry. After The Undertaker dropped the WWF Championship back to Austin following King of the Ring 1999, and an additional loss to him in a First Blood match at Fully Loaded, his relationship with the McMahons dissolved and the Corporate Ministry disbanded.
The Undertaker then began a storyline where he teamed with The Big Show in a tag team known as The UnHoly Alliance, which held the WWF Tag Team Championship twice. After their victory at SummerSlam (1999), The Undertaker suffered a groin tear and was seen limping in several matches. He avoided competing in wrestling matches in the following weeks, instead tyrannically ordering The Big Show to fight all his battles and oblige all his many wishes. To compensate for his lack of physical action, Undertaker became more vocal on the mic, often making smart-aleck remarks and performing commentary at the announcer's table. In an angle that occurred in September 1999 on SmackDown!, Undertaker was fired by Mr. McMahon in a backstage interview when he refused to participate in a casket match against Triple H. In actuality, Undertaker went on a four month hiatus from WWF in order to treat his groin injury. In January 2000, one month before a scheduled return at the Royal Rumble, he tore a pectoral muscle.
By The Undertaker's May 2000 return, he had taken on a drastically different identity from before. He abandoned the somber mortician-themed attires, his funeral dirge ring music, allusions to the supernatural, and the accompanying morbid theatrics. In place of this, he took on a biker identity, riding to the ring on a motorcycle, and wearing sunglasses and bandanas to the ring. His entrance music was replaced with popular rock songs of the time, like Limp Bizkit's "Rollin' (Air Raid Vehicle)", though it was accompanied by the characteristic opening bell gong of The Undertaker's original theme.
Upon his return in May 2000, he took out all the members of the McMahon-Helmsley Faction, which caused him to once again be a fan favorite. He also targeted their leader, WWF Champion Triple H. At King of the Ring, The Undertaker teamed with The Rock and Kane to defeat the team of Triple H, Shane McMahon, and Vince McMahon. Afterward, he was booked to team with Kane to contend for the WWF Tag Team Championship. They defeated Edge and Christian, earning the right to face them the following week for the tag title, which Edge and Christian retained. Kane betrayed The Undertaker by chokeslamming him twice on the August 14 episode of Raw is War. This incident led to another match between the two at SummerSlam, which ended in a no contest as Kane ran from the ring area after The Undertaker removed Kane's mask.
The Undertaker then challenged Kurt Angle for the WWF Championship at Survivor Series. Angle, however, defeated The Undertaker after Kurt switched places with his real life brother, Eric Angle. The Undertaker demanded and was awarded a spot in the Six Man Hell in a Cell match for the WWF Championship at Armageddon. The Undertaker promised to make someone "famous" and did so when he chokeslamed Rikishi off the roof of the cell.
In 2001, The Undertaker reunited with Kane as the Brothers of Destruction, challenging for the WWF Tag Team Championship once again. They received a shot at the title at No Way Out, facing Edge and Christian and then champions the Dudley Boyz in a Tables Match. The Brothers of Destruction dominated almost the entire match but were not the winners. The Undertaker was then booked to defeat Triple H at WrestleMania X-Seven, where he improved his WrestleMania winning streak to 9–0. He and Kane continued a storyline that focused on Triple H, who formed a "surprise alliance" with WWF Champion Stone Cold Steve Austin. The Brothers of Destruction were granted an opportunity to face Triple H and Austin for their titles. After The Undertaker and Kane acquired the WWF Tag Title from Edge and Christian, Triple H pinned Kane after attacking him with a sledgehammer at Backlash, where the Brothers of Destruction dropped the title. With Kane injured, The Undertaker feuded briefly with Steve Austin for his WWF Championship, but at Judgment Day, Austin retained his title.
As part of "The Invasion" storyline, The Undertaker's next nemesis was Diamond Dallas Page, who was obsessively following The Undertaker's wife, Sara. At SummerSlam, The Undertaker and Kane defeated Page and his partner Chris Kanyon in a steel cage match to win the WWF Tag Team Championship. At Survivor Series, The Undertaker teamed with Kane, The Rock, Chris Jericho, and The Big Show to take on The Alliance's Steve Austin, Booker T, Rob Van Dam, Shane McMahon, and Kurt Angle. Angle pinned The Undertaker due to interference by Austin. After the Alliance was defeated, The Undertaker became a villain once again by forcing commentator Jim Ross to kiss Vince McMahon's backside. This was the beginning of a new persona for The Undertaker, as he cut his long hair short and called himself "Big Evil". At Vengeance, The Undertaker defeated Van Dam to capture the WWF Hardcore Championship.
The Undertaker's next storyline began at the Royal Rumble in 2002 when Maven eliminated him by dropkicking him from behind. Subsequently, The Undertaker eliminated Maven in return and brutally assaulted him backstage. On an episode of SmackDown!, The Rock mentioned The Undertaker's elimination at the Royal Rumble, angering The Undertaker. The Undertaker responded by costing The Rock the number one contendership for the WWF Undisputed Championship. The storyline continued when The Rock cost The Undertaker his match with Maven for the Hardcore Championship. The two faced off at No Way Out, where The Undertaker lost due to interference from Ric Flair. This interference began a storyline with Flair, who declined a challenge to wrestle Undertaker at WrestleMania X8, and, as a result, Undertaker assaulted his son David Flair. Flair eventually accepted the match after The Undertaker threatened to inflict the same punishment on Flair's daughter. A no disqualification stipulation was added to the match, and The Undertaker defeated Flair.
After the storyline with Flair, The Undertaker defeated Stone Cold Steve Austin at Backlash to win the number one contendership for the WWF Undisputed Championship. Later that night, he helped Hulk Hogan win his title match against the Undisputed Champion Triple H. The Undertaker then defeated Hogan for his fourth world championship at Judgment Day. The following night The Undertaker was defeated by Rob Van Dam for The WWE Undisputed Championship, however Ric Flair restarted the match and The Undertaker recaptured his championship. On the July 1 episode of Raw, The Undertaker turned into a fan favorite again after defeating Jeff Hardy in a ladder match and raising Hardy's hand as a show of respect. The Undertaker, however, dropped the title at Vengeance to The Rock in a triple threat match that also involved Kurt Angle. The Undertaker was then switched from Raw to SmackDown!, alongside former Raw talent Brock Lesnar, Chris Benoit, and Eddie Guerrero. The Undertaker challenged Lesnar in a title match at Unforgiven that ended in a double-disqualification. Their feud carried over to No Mercy in a Hell in a Cell match. The Undertaker performed in the match with a legitimate broken hand and eventually lost to the champion.
The Undertaker took a leave from wrestling after the Big Show threw him off the stage, sparking a feud. The Undertaker returned at the Royal Rumble in 2003. He immediately continued his feud with Big Show and defeated him by submission at No Way Out with a triangle choke. A-Train entered the storyline by attempting to attack The Undertaker after the match, but Nathan Jones came to his aid. The storyline resumed as The Undertaker began to train Jones to wrestle, and the two were scheduled to fight Big Show and A-Train in a tag team match at WrestleMania XIX. Jones, however, was removed prior to the match, making it a handicap match, which The Undertaker won with the help of Jones.
Over the remainder of the year, The Undertaker entered a brief feud with John Cena and was booked to have two WWE Championship opportunities. The first, on the September 4 SmackDown!, against Kurt Angle, ended in a no contest, due to interference from Brock Lesnar. The second, at No Mercy, was a Biker Chain match between The Undertaker and Lesnar, which Lesnar won with the help of Vince McMahon. This match resulted in a feud with McMahon, culminating at Survivor Series where The Undertaker lost a Buried Alive match against McMahon when Kane interfered. The Undertaker disappeared for some time following the match, with Kane claiming that he was "dead and buried forever."
In the storyline leading up to WrestleMania XX, Kane was haunted by vignettes proclaiming The Undertaker's return. The first was during the Royal Rumble when The Undertaker's bells tolled, distracting Kane and allowing Booker T to eliminate him. At WrestleMania XX, The Undertaker, accompanied by Paul Bearer, returned under his resurrected "Deadman" identity (hybrid version) and defeated Kane. At the following Smackdown! Pay-Per-View Judgment Day, The Undertaker would go on to defeat Booker T. Three months later, Bearer was kidnapped by the Dudley Boyz at the direction of Paul Heyman, who then took "control" of Undertaker. On Smackdown Undertaker attacked both Rob Van Dam and John Cena. The following week Cena confronted The Undertaker and was booked into a match by then General Manager Kurt Angle to face The Undertaker which The Undertaker went on to win after hitting Cena with his chain and delivered a Tombstone. At The Great American Bash The Undertaker fought a handicap match against the Dudleys, with the stipulation that if he didn't lay down and purposely lose, Heyman would bury Bearer in cement. The Undertaker won and stopped Heyman from burying Bearer, then buried him anyway, explaining that Bearer was merely a liability now and that he had no use for him anymore.
After defeating the Dudley Boyz, The Undertaker began a feud by challenging then WWE Champion John "Bradshaw" Layfield (JBL) to a title match at SummerSlam, which The Undertaker lost by disqualification. At No Mercy, The Undertaker and JBL competed in the first ever "Last Ride" match, although The Undertaker lost after Heidenreich interfered. After a brief program with Heidenreich, The Undertaker turned his focus to the WWE Championship once again. Along with Eddie Guerrero and Booker T, he challenged JBL to a championship rematch at Armageddon in a Fatal Four-Way match, in which The Undertaker was unsuccessful, again due to Heidenreich's interference. The feud culminated in a Casket match between The Undertaker and Heidenreich at the Royal Rumble, where The Undertaker sealed Heidenreich in a casket for the victory.
Soon afterward, Randy Orton challenged The Undertaker to a match at WrestleMania 21, in a storyline where Orton claimed that he would end The Undertaker's WrestleMania winning streak. Even with help from his father "Cowboy" Bob Orton, Randy failed, and The Undertaker improved his WrestleMania record to 13–0. He returned for the June 16 episode of SmackDown! but lost to JBL, thanks to interference from Randy Orton. After The Great American Bash, The Undertaker became the number one contender to the World Heavyweight Championship, a position that JBL felt he should have. As part of the feud, on the following SmackDown!, The Undertaker lost a number one contender match against JBL, once again due to interference from Orton. With this, The Undertaker resumed his feud with Orton. At SummerSlam, Orton defeated The Undertaker in a WrestleMania rematch. The storyline intensified as the two taunted each other with caskets, leading to a casket match at No Mercy, in which The Undertaker lost to Randy and his father "Cowboy" Bob Orton. After the match, the Ortons poured gasoline on the casket and set it on fire. When the charred casket was opened, however, The Undertaker had once again vanished. He returned at the Survivor Series, emerging from a burning casket. The Undertaker returned to SmackDown! in early December to haunt Orton and set up a Hell in a Cell match at Armageddon. After winning the match, Taker took a brief hiatus from wrestling.
In early 2006 at the Royal Rumble, The Undertaker returned during Kurt Angle's celebration of his World Title defense against Mark Henry on a horse drawn cart, signaling for a title shot. As part of their storyline feud, The Undertaker lost his match with Angle at No Way Out after a thirty minute bout. Undertaker cornered Angle after the match and told him he was not finished with him; however during a rematch on SmackDown! Henry attacked The Undertaker from behind, costing him the title. This led to The Undertaker challenging Henry to a Casket match at WrestleMania 22, and Henry - like Orton a year before - vowed to end Undertaker's WrestleMania winning streak. The Undertaker defeated Henry to become 14–0 at WrestleMania, keeping his undefeated streak alive. During a rematch on the next episode of SmackDown!, The Great Khali made his debut and assaulted The Undertaker to transition into a new storyline.
The Undertaker was not heard from until the May 5 episode of SmackDown!, as Theodore Long delivered a challenge from The Undertaker to Khali for a match at Judgment Day. The Undertaker lost to Khali, and he did not appear again until the July 4 episode of SmackDown!, when he accepted Khali's challenge to a Punjabi Prison match at The Great American Bash. Khali, however, was removed from the match and was not medically fit and was replaced by ECW Champion The Big Show, over whom The Undertaker gained the victory. In the storyline, Teddy Long replaced Khali with Big Show as punishment for an attack on The Undertaker shortly before the match. Khali was then challenged to a Last Man Standing match at SummerSlam after interfering in The Undertaker's match with World Heavyweight Champion King Booker. Khali refused the challenge for SummerSlam, though Long made the match official for the August 18 episode of SmackDown! instead. The Undertaker won the match by striking Khali with the steel stairs, delivering several chair shots, and finishing him with a chokeslam.
The Undertaker's next match was with WWE United States Champion Mr. Kennedy at No Mercy but was disqualified in the match after he hit Kennedy with the championship belt. On the November 3 episode of SmackDown!, The Undertaker reunited with Kane to form the Brothers of Destruction for the first time in five years, defeating the reluctant opposition team of Mr. Kennedy and MVP, with whom Kane was feuding with at the time. As part of the storyline, Kennedy defeated The Undertaker in a First Blood match at Survivor Series after interference from MVP, but finally defeated Kennedy in a Last Ride match at Armageddon. The two continued to feud into 2007 as Kennedy cost The Undertaker two World Heavyweight Championship opportunities for a championship match at the Royal Rumble.
The Undertaker won his first Royal Rumble match at the 2007 event, becoming the first man to enter the Rumble at number 30 and win the match. He then began a storyline with Batista, whom he defeated at WrestleMania 23 to win his first World Heavyweight Championship. At Backlash in a Last Man Standing match, they had a rematch that ended in a draw when neither man was able to answer the ten-count, resulting in The Undertaker retaining the Championship. On the May 11 episode of SmackDown!, The Undertaker and Batista participated in a steel cage match that ended in a draw when both men's feet touched the floor at the same time. After the match, Mark Henry returned and assaulted The Undertaker. Immediately after the assault, Edge cashed in his Money in the Bank title shot, and The Undertaker dropped the World Heavyweight Championship to Edge. As The Undertaker laid in the ring, druids appeared and carried him to the backstage area.
During Undertaker's rehabilitation, Mark Henry quickly defeated local jobbers and bragged about his assault on Undertaker, until vignettes began playing promoting The Undertaker's return. The Undertaker returned at Unforgiven, defeating Henry and again on SmackDown! two weeks later. Batista and The Undertaker reignited their feud at Cyber Sunday with the fans choosing the special guest referee Stone Cold Steve Austin, but Batista retained the world title. They battled again inside a Hell in a Cell at Survivor Series where Edge returned and interfered to help Batista retain the World Heavyweight Championship. In response to this, The Undertaker delivered a Tombstone piledriver to General Manager Vickie Guerrero, on the next SmackDown!, sending her to the hospital. Returning Assistant-General Manager Theodore Long declared a Triple Threat match for the title at Armageddon, which Edge won.
At No Way Out, The Undertaker defeated Batista, Finlay, The Great Khali, Montel Vontavious Porter, and Big Daddy V in an Elimination Chamber, to become the number one contender for Edge's World Heavyweight Championship at WrestleMania XXIV. He defeated Edge at WrestleMania with his Hell's Gate submission hold, to win his second World Heavyweight Championship and elevate his undefeated streak at WrestleMania to 16–0. In a WrestleMania rematch, The Undertaker defeated Edge once again at Backlash to retain the World Heavyweight Championship. Vickie Guerrero announced that The Undertaker's Hell's Gate was an illegal hold and stripped him of the title. The Undertaker battled Edge for the vacant title at Judgment Day, which he won by countout. Vickie ordered that the title remain vacant, because titles cannot change hands in this way. Edge and The Undertaker faced each other again for the vacant championship at One Night Stand in a Tables, Ladders, and Chairs match, which The Undertaker lost after interference from La Familia. As a result of the stipulation, Undertaker was forced to leave WWE.
On the July 25, 2008 episode of SmackDown, Vickie Guerrero announced that she had reinstated The Undertaker, and that Edge would face him at SummerSlam in a Hell in a Cell match, which The Undertaker won. After the match, The Undertaker chokeslammed Edge from the top of a ladder and through the ring canvas. Following this match, Guerrero tried to make a peace offering with The Undertaker on SmackDown by apologizing, but The Undertaker told her that he is not the forgiving kind. At Unforgiven, as The Undertaker approached the ring to "take Guerrero's soul" and take her in a casket, the Big Show, who appeared at first to aid the Undertaker, betrayed and assaulted him. As a result of this altercation, The Undertaker and Big Show faced each other in a match at No Mercy, where the Big Show knocked The Undertaker out with two hook punches in the forehead and a punch to the back of Undertaker's head. At Cyber Sunday, The Undertaker defeated the Big Show in a Last Man Standing match after applying Hell's Gate. The Undertaker then went on to defeat the Big Show at Survivor Series in a casket match, to end the feud. At No Way Out, The Undertaker was part of the WWE Championship Elimination Chamber match; however, he was unsuccessful at winning the match. He then became embroiled in a long time feud with Shawn Michaels over his WrestleMania undefeated streak and the fact that The Undertaker had never defeated Michaels in a singles match previously. The feud culminated in a match at WrestleMania XXV which The Undertaker won to extend his WrestleMania streak to a perfect record of 17–0. On the April 24 episode of SmackDown, Big Show defeated him in a singles match by knockout after the match, Undertaker attacked Big Show. After SmackDown, Undertaker took another hiatus from WWE on April 25, 2009.
After the four month hiatus, The Undertaker returned at SummerSlam in August by attacking CM Punk, who had just won the World Heavyweight Championship from Jeff Hardy in a Tables, Ladders, and Chairs match. At Breaking Point, The Undertaker faced Punk in a submission match. The Undertaker had originally won the match with his Hell's Gate submission hold, but the match was restarted by SmackDown General Manager Theodore Long, who ruled that the ban placed on the move by Vickie Guerrero was still in effect. Punk went on to win the match with his Anaconda Vise when referee Scott Armstrong called for the bell, despite Undertaker never submitting in a recreation of the Montreal Screwjob, which took place in the same venue in 1997. On the September 25 episode of SmackDown, Theodore Long announced that the ban had now been officially lifted, after being released from a casket that The Undertaker had apparently placed him in. The feud between the two continued and at the Hell in a Cell pay-per-view, The Undertaker won the World Heavyweight Championship from Punk in a Hell in a Cell match. The Undertaker successfully defended the title against CM Punk on SmackDown, in a Fatal Four Way match at Bragging Rights, and in a Triple Threat match at Survivor Series. He faced Batista at TLC: Tables, Ladders & Chairs for the championship, and won when the match was restarted by Long, after Batista had originally won after utilising a low blow.
He lost the World Heavyweight Championship to Chris Jericho after interference from Shawn Michaels. Undertaker had been rebuffing Michaels' requests for a WrestleMania rematch, but the night after Elimination Chamber he agreed to the match on the condition that Michaels' career was on the line. At WrestleMania, The Undertaker defeated Michaels to end his career in a match with no countouts or disqualifications.
After a hiatus (which included wrestling two matches on Raw), he returned to SmackDown on May 28, defeating Rey Mysterio to qualify for a spot in the Fatal 4-Way pay-per-view to compete for the World Heavyweight Championship. During the match, The Undertaker suffered a concussion, broken orbital bone, and broken nose; he was visibly bleeding profusely on camera by the end of the match. To cover for the injury, Kane revealed The Undertaker had been found in a vegetative state; Mysterio took his place in the match and won the World Heavyweight Championship. While attempting to learn which superstar had attacked The Undertaker, Kane defeated Mysterio to win the World Heavyweight Championship. Kane and Mysterio continued to clash as they accused one another of being the assailant behind the attack.
At SummerSlam, the Undertaker returned to confront Kane and Rey Mysterio, only to be overpowered and Tombstoned by Kane. With Kane revealed as his attacker, the two feuded for the next few months over the World Heavyweight Championship. After losing to Kane at Night of Champions, Paul Bearer returned as Undertaker's manager on an episode of SmackDown. However, Bearer attacked him at Hell in a Cell to help Kane win once again. The feud ended at Bragging Rights when The Nexus helped Kane defeat Undertaker in a Buried Alive match. In reality, he needed medical treatment for his injury.
After the 2011 Royal Rumble, promotional videos began airing, showing The Undertaker entering and standing within a Western-style old house on a rainy desert. Each promo would end with the date 2–21–11 being burned into the screen. On the February 21 episode of Raw, The Undertaker returned. Before he could speak, Triple H returned after an eleven-month absence and confronted him. The two challenged each other to a match at WrestleMania in a unique interaction involving no verbal or physical exchanges. The match was later announced as a No Holds Barred match on WWE's website. On the March 28 episode of Raw, the two had a last confrontation with the presence of Shawn Michaels before WrestleMania that involved praise, demonstrations of respect, and conflicts. Finally, at WrestleMania XXVII, after surviving three Pedigrees and a Tombstone Piledriver, Undertaker forced Triple H to tap out to Hell's Gate, extending his streak to 19–0. Following the match, The Undertaker was carried away from the ring on a stretcher.
On the January 30, 2012 episode of Raw, The Undertaker returned after a ten-month hiatus to confront Triple H. On the February 13 episode of Raw, Triple H refused the Undertaker's challenge for a WrestleMania rematch, which led to Undertaker appearing on the TitanTron and declaring that vengeance would be his. After the Undertaker accused Triple H of living in the shadow of Shawn Michaels on the February 20 episode of Raw, Triple H accepted the challenge on the condition that it be a Hell in a Cell match; Michaels was later inserted as referee in the match. At WrestleMania XXVIII, The Undertaker defeated Triple H to extend his streak to 20-0. After the match, Undertaker and Michaels carried Triple H to the entrance stage, where the three of them hugged each other.
The Undertaker next appeared on the 1000th episode of Raw on July 23 to help Kane, who had been confronted by Jinder Mahal, Curt Hawkins, Tyler Reks, Hunico, Camacho, and Drew McIntyre. The six attacked Undertaker and Kane but were overpowered, despite outnumbering them. Kane and Undertaker delivered two simultaneous Chokeslams, followed by two simultaneous Tombstone Piledrivers to Hawkins and Hunico and cleared the ring. This hinted that Undertaker had forgiven Kane's betrayal in late 2010. During his speech at the 2012 Slammy Awards, Triple H stated: "You have not seen the last of the Undertaker."
On February 23, 2013, Undertaker made an off-screen appearance at a SmackDown house show in Waco, Texas, teaming up with Sheamus in a tag team match to defeat Damien Sandow and Wade Barrett. His televised return was on Old School Raw on March 4, where he opened the show by performing his signature entrance. CM Punk, Randy Orton, Big Show, and Sheamus fought in a Fatal Four-Way match to determine who would face him at WrestleMania 29, which Punk won. Following this, Undertaker made another entrance and stared Punk down. After the real-life death of Paul Bearer on March 5, 2013, a storyline involving Punk regularly spiting The Undertaker through displays of flippance and disrespect towards Bearer's death began. Punk interrupted The Undertaker's ceremony to honor Bearer on Raw, stealing the trademark urn and later using it to attack Kane, humiliate the Brothers of Destruction and mock Bearer. Undertaker would defeat Punk at WrestleMania 29 to extend his streak to 21–0 and took back the urn after the match. The following night on Raw, Undertaker once again attempted to pay his respects to Paul Bearer but was once again interrupted, this time by The Shield. The Shield members attempted to initiate an attack, but their efforts were thwarted by Team Hell No (Kane and Daniel Bryan) making the save. Undertaker wrestled his first Raw match in three years on the April 22 episode, teaming with Kane and Bryan against The Shield in a losing effort. Four days later, he wrestled his first Smackdown match in three years, defeating Shield member Dean Ambrose in a singles match via submission. Afterwards, Undertaker would be brutally attacked by Ambrose and the rest of The Shield before they powerbombed him through the announce table.
On the February 24, 2014 episode of Raw, the Undertaker returned to confront Brock Lesnar and accepted his challenge for a match at WrestleMania XXX. After a long and "methodical" match, Lesnar defeated Undertaker by pinfall to end the streak.
In early 2015, Bray Wyatt began appearing in cryptic segments seemingly about The Undertaker, until the challenge was finally laid down at WWE Fastlane. Undertaker would then make his first official appearance since his loss at WrestleMania 30, sporting longer hair, defeating Wyatt at WrestleMania 31. At Battleground, Undertaker would return during the WWE World Heavyweight Championship match between Seth Rollins and Brock Lesnar, attacking Lesnar, resulting the match ending in a no contest. On the following July 20 episode of Raw, it was officially announced that Undertaker would face Lesnar in a WrestleMania XXX rematch at SummerSlam. At the pay-per-view, Undertaker controversially defeated Lesnar; Undertaker tapped out to a Kimura Lock by Lesnar and the bell rang, but the referee did not see the tapout and allowed the match to continue. Lesnar then passed out to Undertaker's submission hold, Hell's Gate. At Night of Champions, it was announced that, in a rubber match, Undertaker would face Lesnar in a Hell in a Cell match at Hell in a Cell. Throughout this period, Undertaker's stance as either a face or a heel was widely debated among WWE fans due to his dirty tactics against Lesnar. On October 17, 2015, at a house show in Mérida, Mexico,The Undertaker teamed with Kane reuniting The Brothers of Destruction to take on Luke Harper and Braun Strowman of The Wyatt Family which they won after Harper tapped out to The Undertaker's Hell's Gate. Undertaker appeared on the October 19 edition of Monday Night RAW, trying to goad Brock Lesnar into a fight.
At Hell in a Cell, the Undertaker was defeated by Lesnar after Lesnar hit him with a low-blow and delivered the third F-5 of the match. Afterwards, Undertaker was given a standing ovation by the crowd. However, he was attacked and ambushed by the entire Wyatt Family. They then carried out the downed Undertaker from the ring. Bray Wyatt explained the following night on Raw that he wanted to "claim" the Undertaker's spirit and wasn't going to stop until he reached his goal. Kane interrupted in an attempt to avenge his older brother's suffering the night before. However, this was a trap and as Kane cornered Bray, the rest of the Wyatts ambushed Kane and carried him away like they did to the Undertaker the night before. On the November 9 edition of Raw, The Brothers of Destruction returned and attacked The Wyatt Family. Undertaker & Kane defeated the team of Bray Wyatt & Luke Harper at Survivor Series after the Undertaker hit Harper with a tombstone piledriver for the pinfall victory.
On the February 22, 2016 episode of Raw, Vince McMahon placed his son Shane McMahon, who returned to WWE for the first time since 2009, in a Hell in a Cell match at WrestleMania 32 against The Undertaker with the stipulation that if Shane wins, he gains control of Raw. The following week on Raw, The Undertaker would make his first appearance since 2015, warning Vince McMahon of the consequences of placing his son in a match with him, placing a choke hold on McMahon before making his exit. On the March 14 episode of Raw, The Undertaker confronted both Vince and Shane McMahon. The confrontation ended with The Undertaker and Shane McMahon in a brawl. Vince McMahon, shoved Shane into a chokeslam by The Undertaker, ending the show with him standing over Shane McMahon. The following week on the March 21 episode of Raw, Vince McMahon "upped the ante" by announcing that, should The Undertaker lose the match at WrestleMania, it would be his last match at the event. At the event on April 3, Undertaker defeated Shane McMahon.
After going undrafted in the 2016 WWE draft, The Undertaker made his return for the first time since WrestleMania 32 for SmackDown Live's 900th episode on November 15, 2016, aligning himself with the SmackDown brand. The Undertaker interrupted Edge's Cutting Edge segment. He stated that he wouldn't let WrestleMania define him and issued a warning to Team SmackDown, telling them not to lose against Team Raw at Survivor Series. After SmackDown went off air, the Undertaker joined Kane onstage as they raised their arms.