WrestleMania XIV (29/3/98)

The first singles match between the two storyline brothers was perhaps the best of the lot. Kane had been heavily protected since debuting in October by going on an unbeaten rampage. Undertaker had not wrestled since Kane cost him a casket match against Shawn Michaels at Royal Rumble. These factors combined to give their showdown a major sense of anticipation and intrigue. The sheer spectacle and drama carried it through. ‘Taker won the match, eventually, needing three Tombstones to put his fire-loving younger sibling away.
Mayhem in Manchester (4/4/98)
Less than a week after their WrestleMania XIV collision, the two behemoths met again in Manchester, England in the main event of the promotion’s aborted U.K. pay-per-view (the event ended up a glorified house show). Due to a mix-up with his luggage, Undertaker wrestled the bout in his casuals, giving fans a first glimpse––two years early––of the ‘American Badass’. This time, one Tombstone was sufficient to put Kane away.
Unforgiven ’98 (24/4/98)

The WWF’s first ever Inferno Match was quite a spectacle. Real flames surrounded the ring, jumping high into the air whenever either man took a bump. Once the novelty wore off the plodding action–– severely limited by the presence of the flames––offered little to sustain audience interest. Undertaker won again after setting Kane’s (prosthetic) arm on fire. It was expected that since Kane had put over Undertaker twice in major PPV matches his defeat would be the end of the character––as was the case with most monsters who feuded with the ‘Dead Man’. How wrong that turned out to be.
Monday Night Raw (1/6/98)
Kane finally beat ‘Taker thanks to help from Mankind, making him the number one contender to Steve Austin’s WWF Title at King of the Ring (which he won). The attack also set up that Hell in a Cell battle between Mankind and Undertaker at the pay-per-view.
Breakdown ’98 (27/9/98)

In a seemingly never-ending brawl that was amongst the weakest main events of the Attitude Era, Undertaker and Kane––who were now in cahoots––pinned Steve Austin simultaneously in a three-way, relieving him of his WWF Title. Because the double pin left no clear winner, the title was declared vacant.
Judgment Day ’98 (18/10/98)
As bad as the Breakdown headliner was it could come close to the depths traversed by this snoozer between the two brothers. With the vacant WWF Title on the line and Austin as guest ref, there should have been enough going on to retain interest. Alas, the contest was so laborious that fans chanted “boring” throughout. The finish was farce typical of the era, as Austin dropped both combatants with a Stunner and declared himself the winner.
Monday Night Raw (19/10/98)
Remarkably, a Casket Match between the duo on Raw the next night was perhaps even worse than their Judgment Day debacle. Three-minutes of rubbish non-action ended without a winner when both men smashed their way out of the casket then casually left. Down there with some of Raw’s worst ever matches.
Survivor Series ’98 (15/11/98)

With the face and heel roles now reversed, Undertaker was forced to drop the majority of his popular schtick (the rope walk, sit-ups, etc), leaving him with little else in his arsenal than copious punches and, in the case of this match, an interminably long leg grapevine. At least there was a finish this time: ‘Taker put Kane away with a Tombstone after a distraction from Paul Bearer at ringside, sending him through to the semi-finals of Vince Russo’s optimum magnus opus––the ‘Deadly Game’ tournament.
Monday Night Raw (22/2/99)
The first Inferno Match to take place on Raw was more angle than wrestling match, with the plot centred around the contents of a mysterious black box given to Vince McMahon by Paul Bearer. It turned out to be Stephanie McMahon’s childhood teddy bear, which caused Vince to have a meltdown. ‘Taker won the match by setting Kane’s foot on fire then burned the bear as McMahon wept in the aisle. The Attitude Era, ladies and gentleman.
SummerSlam 2000 (27/8/00)

The first major singles bout between the pair in over a year may have been aesthetically different due to Kane removing the sleeves from his outfit and ‘Taker donning a blue denim shirt and riding a motorbike as the ‘American Badass’, but little else had changed. A punch-kick-rinse-repeat bore ended without a finish (some things never change), when Undi ripped off Kane’s mask, causing his music to inexplicably play and Kane to leave.
Monday Night Raw (27/11/00)
More punching and another non-finish here, as Edge & Christian ran in to cause a DQ after Undertaker had dominated proceedings. A colossal bore.
WrestleMania XX (14/3/04)

Having resisted the urge to pit the two against each other in any major singles bout for almost four years, WWE went back to the well for ‘Taker’s return match as the ‘Dead Man’. Making his first appearance since Survivor Series the previous November, Undi made an entrance far more memorable than the match itself, which was a basic paint-by-numbers affair. Obviously, Undertaker won. Also notable for being one of scant few matches to have taken place at WrestleMania more than once.
SmackDown (4/4/08)
Much had changed four years later when the duo met again on SmackDown, with Kane the ECW Champion and Undertaker carrying the World Heavyweight Title. Both had snared the belts a few days earlier at WrestleMania XXIV. Predictably the bout ended in a non-finish, when Edge, Chavo Guerrero and others ran in to set up their respective Backlash matches.
Night of Champions ’10 (19/9/10)

And so began the most successful series of matches against his eternal nemesis of Kane’s career. Now World Heavyweight Champion, Kane fended off Undertaker in a lengthy No Holds Barred contest, beating him cleanly with a Tombstone.
Hell in a Cell ’10 (3/10/10)

The first Hell in a Cell meeting between the two ended in controversy when Paul Bearer turned on ‘Taker for the umpteenth time. As Undi was about to hit a Tombstone, the lights went out and Bearer blinded him with a bright light emitted from the urn. Bearer then gave the urn to Kane, who drilled his brother with it to win the bout. The match and the execution of the finish were shoddy, resulting in a deservedly silent reaction from the crowd.
Bragging Rights ’10 (24/10/10)

The final pay-per-view meeting of the two siblings––for now at least––came almost eight years ago in the middle of a B-level pay-per-view. Fittingly, it was a Buried Alive match, won again by Kane, when the Nexus interfered to aid the ‘Big Red Machine’. Some magic-assisted dirt dropping later and ‘Taker––like this rivalry––was dead and buried.
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