The Undertaker has a long and storied history in casket matches, dating back to the 1992 edition of Survivor Series. Contrary to popular belief, this was not the first casket match in professional wrestling history. That distinction belongs to a little known match out of the Houston Wrestling territory in 1980 between Dusty Rhodes and Ivan Koloff.
The WWF/E version of the first casket match featured The Undertaker and the Ugandan Giant Kamala. For weeks following Kamala's top rope splash onto The Undertaker at SummerSlam 1992, The Undertaker terrorized Kamala by having Paul Bearer roll out caskets in the middle of Kamala's matches, causing him to run out of the arena. The lead up to the match included The Undertaker cutting a promo in some sort of sinister workshop building a custom coffin for the rather large Kamala, complete with a lid matching Kamala's body paint.
The match itself was little over five minutes long in what amounted to an extended squash. Kamala worked in a few body slams, only for The Undertaker to perform his patented sit-up and eventually befall Kamala. Interestingly, this bout required The Undertaker to pin Kamala before rolling him into the casket and nailing it shut. While the match was intended to convey the spookiness and mystical surrounding The Undertaker, Kamala's frequent attempts of escape added some comedic effect.
The next casket match wouldn't take place until the Royal Rumble in 1994. This time, The Undertaker challenged then WWF champion Yokozuna for the title. The lead up to the match mirrored the previous casket match, with The Undertaker cutting promos that worked to terrify Yokozuna. This match ended up being much longer than the original, clocking in at nearly 16 minutes. The tone of this match was considerably more intense and violent while doing away with the pin requirement and any disqualification rules.
What set this match apart was the massive number of interferences on behalf of Yokozuna, including Jeff Jarrett, Crush, Bam Bam Bigelow, Diesel, and many more. The Undertaker valiantly fought off his attacks, further endearing the crowd to his character until the numbers eventually became too great for him to overcome. One of the classic images from the match would be The Undertaker's urn opening in the ring and releasing a rather bountiful amount of green smoke. Yokozuna would eventually end the match by rolling The Undertaker into the casket, shutting the lid and retaining the WWF Championship.
While the match itself was entertaining, what followed was an example of one of The Undertaker's earliest incredible demonstrations of his supernatural character. As Yokozuna and his cast of attackers rolled the casket toward the entrance video screen, The Undertaker's classic gong hit and his image inside the casket appeared on the video screen. He proceeded to cut one of his cryptic afterlife promos from inside the casket which culminated with The Undertaker's soul in physical form ascending from the screen and into the rafters. It was truly a sight to behold at the time, something fans had never seen before. This would be the first truly classic moment in the history of The Undertaker's casket matches.
The two behemoth superstars would face each other in a casket rematch at Survivor Series 1994, in another hard hitting, violent match, only this time with Chuck Norris as the special guest referee. King Kong Bundy, Bam Bam Bigelow and Jeff Jarrett would once again make their way out to ringside but never made it past Norris. The only superstar to actually enter the ring was IRS, who from behind applied a sleeper hold to The Undertaker and rolled him into the casket. Unfortunately for Yokozuna, The Undertaker was able to rise before the lid was shut. The match ended following a big boot to the face of Yokozuna that knocked him backward and into the casket which The Undertaker shut for the win.
The WWF kept the ball rolling on casket matches the next year at the In Your House 2 event during the feud between Kama and The Undertaker. Kama had stolen The Undertaker's urn and melted it into a giant gold necklace. Of course the Undertaker didn't take kindly to his parent's ashes and memorial being destroyed. While the match took place during an ongoing feud, it did not feature on the main card, it would be a dark match following the main show.
This was a match many thought they would see when Kama was under the Papa Shango gimmick, but that match never came to fruition. Because Kama was of relatively normal size, a normal coffin was used for this match. The sight of a more typical coffin actually added to the dread and eeriness intended from a match like this. The Undertaker defeated Kama in a largely uneventful match that served more to please the live audience.
The two would face again in a second casket match at SummerSlam 1995. The match followed Kama's attack the week before on The Undertaker's followers, The Creatures of the Night. This match shown on the main card would once again feature the oversized casket seen in the Yokozuna matches. This time the casket included an upward facing camera at the base. Kama and Undertaker would go on to have a match largely reminiscent of the previous encounter. The main difference coming in an entertaining spot where both men fall into the oversized casket and the lid closing on them. The match did not end in a draw as both men fought out of the casket and made it back into the ring. The Undertaker went on to pick up the victory following a chokeslam, tombstone piledriver and rolling Kama into the casket.
Later that year Mabel found himself in a feud with The Undertaker. The recently crowned King of The Ring would be the first to really test The Undertaker ahead of a casket match by cutting his own promos in anticipation of the match, stealing the necklace that served as the remnants of the urn and even vandalizing The Undertaker's casket. This was also during the time The Undertaker wrestled with a mask, very reminiscent of the future Kane masks, following a legit injury to his orbital bone. In kayfabe this was due to Mabel smashing The Undertaker's face with 600 pound leg drops.
The two met at In Your House 5 in December 1995 in the casket match. For those interested in some trivia, you can find The Hardy Boyz as part of the crew carrying Mabel on a throne into the arena ahead of the match. The match itself was short as The Undertaker boots Mabel into the casket a few minutes into the match. Mabel's manager and former tag team partner Mo would try to interfere but found himself thrown into the casket as well following a chokeslam. The Undertaker retrieved the necklace from around Mo's neck and shut the casket for the victory.
The Undertaker's next casket match featured another one of WWE's most enigmatic characters of all time, Goldust. The two squared off at In Your House 8 for the Intercontinental Championship featuring a custom gold casket with Goldust's star logo printed on the lid.. This was arguably one of the better wrestling matches in The Undertaker's series of casket matches. Goldust was able to showcase his wrestling prowess until succumbing to a tombstone piledriver (he actually delivered his own, much weaker looking, tombstone earlier in the match). This was not to be The Undertaker's night, however. When The Undertaker demanded the referees open the casket, out popped Mankind who immediately applied the Mandible Claw and knocked out The Undertaker into the casket that was then closed for a Goldust victory.
The ensuing feud with Mankind led to one of the most consequential moments of The Undertaker's career, Paul Bearer betraying him and joining forces with Mankind. After a brief hiatus, The Undertaker returned to feud with Vader and the two clashed at Royal Rumble 1997. Paul Bearer interfered and cost The Undertaker the match. The two superstars locked up again in a casket match at a house show in Madison Square Garden. At the time the match could only be seen by the live audience and those who had the MSG network in New York. The match was as violent and hard-hitting as any match involving Vader and The Undertaker could be. Paul Bearer lurked at ringside as Vader's manager. The match eventually ended the same way as the Goldust match with The Undertaker rolling Vader to the casket only for Mankind to emerge again to apply the Mandible Claw and secure the victory for Vader.
The following year at Royal Rumble 1998 The Undertaker and Shawn Michaels clashed in a casket match for the WWF Championship. Michaels and The Undertaker were in the midst of their earliest epic feud, which included their classic Hell in a Cell. During this time Shawn Michaels was the leader of Degeneration-X at their peak.
On this night Michaels and The Undertaker put on what today is still the best casket match ever contested. The in-ring action was as solid as ever, with some truly incredible casket spots including The Undertaker's tombstone on Michaels that landed both in the casket. The match unfortunately is also where Michaels, early on, injured his lower back when he was dropped toward the casket. This would be the start of his back problems that led to his first retirement.
Predictably, DX and it's myriad members got involved to help secure the victory for Michaels and retain the championship. Kane, The Undertaker's half-brother and partner appeared to what everyone believed was to save the match for his kin. Kane then shocked the world by turning on The Undertaker, leading to Michaels retaining the championship. Following the bout, in one of the most striking visuals in the history of casket matches, Kane took an axe to the casket with The Undertaker in it and proceeded to light it on fire. Thus began the new Kane and Undertaker feud.
Later that year The Undertaker's feud with Kane led to a casket match on Monday Night Raw, the first to be featured on regular WWE programming. The match ended in a draw after Kane and The Undertaker destroyed the casket by fighting each other in it and The Undertaker abandoning Kane to chase after Paul Bearer.
Monday Night Raw again played host to the next casket match where The Undertaker took on The Rock in May 1999. The Rock was mired in a feud with Triple H at the time who interfered and cost The Rock the match. Triple H beat down The Rock with a sledgehammer, locked him in the casket and proceeded to beat the casket with the sledgehammer.
The Undertaker wouldn't appear in another casket match until Royal Rumble 2005. On this night he took on John Heidenreich who was a thorn in the entire locker room's side. Heidenreich's gimmick at the time was a psychopath who would repeatedly run in on random matches, attack babyfaces and recite hateful poetry. His feud with The Undertaker followed Heidenreich costing him the WWF Championship twice against John Bradshaw Layfield.
JBL tries to interfere on Heidenreich's behalf but the two heels weren't prepared for the surprise waiting inside the casket. Kane emerged to assist The Undertaker and clear the way for the latter to tombstone and chokeslam his way to victory.
The next casket match is particularly interesting, coming in the middle of The Undertaker and Randy Orton feud of 2005. Randy's dad, “Cowboy” Bob Orton became involved following the WrestleMania and SummerSlam matches which his son and The Undertaker split. At No Mercy 2005, father and son teamed up in the first handicapped casket match that stipulated The Undertaker must lock both Ortons in the casket for the victory. The Undertaker seemed well on his way after knocking Bob Orton into the casket. Victory proved elusive, however, when Bob Orton emerged from the casket spraying a fire extinguisher into The Undertaker's face leading to an RKO from Randy. The Ortons rolled The Undertaker into the casket to secure the victory.
The casket match, in it's 14th edition in WWE, finally made it to the grandest stage at WrestleMania 22. The Undertaker put his famous WrestleMania streak on the line against Mark Henry. This match is more notable for Mark Henry's rise as a main event superstar who was granted a match with The Undertaker at WrestleMania. The streak survived this night following The Undertaker's victory. Mark Henry got a chance at revenge two years later on a “WrestleMania Rewind” edition of Monday Night Raw. The match played out mostly the same, ending with another Undertaker Victory.
On the Halloween edition of SmackDown in 2008, WWE took advantage of the occasion and pitted Chavo Guerrero against The Undertaker in a casket match. The Big Show stalked at ringside due to his feud with The Undertaker that saw the former chokeslammed at No Mercy the Sunday before. The Undertaker won the match in what ultimately served as a progression of the Big Show feud.
Big Show's feud with the Undertaker came to a head at what is—until the Greatest Royal Rumble, of course—Undertaker's last casket match at Survivor Series 2008. It was a back and forth match until Big Show destroyed the casket in order to avoid certain defeat. During an escape he was blocked by the emergence of a second casket. Undertaker went on to win this match following an Irish whip into the casket, which fell over and shut for the victory.
The Undertaker's history with the casket match is a winning legacy, with a record of 11-5-1. It's near certain he will improve that record by a win following his encounter with Rusev at the Greatest Royal Rumble. The casket match is without a doubt one of the most entertaining and storied gimmick matches in WWE history. Outside of Hell in a Cell and WrestleMania, the casket match is one of the most important series of matches in the illustrious career of The Undertaker.