Mankind and The Undertaker are two legendary wrestlers in the business who had remarkable in-ring careers. Their rivalry kickstarted on the Raw after WrestleMania 12, and their feud was on-and-off for the better part of two years. No one troubled The Undertaker consistently until Mankind was a legitimate threat to the Deadman.
The future WWE Hall of Famers battled in a series of gimmick matches and there was a shocking betrayal that took place in one of their matches. They always brought out the best in each other which made their matches captivating to watch. As expected, not all of their matches were five-star epics, but the majority were watchable affairs.
10 Raw (3/1/99)
Mr. McMahon sat at the commentary table, and he announced that The Undertaker and Big Boss Man would clash in a Hell in a Cell match at WrestleMania 15. Nevertheless, The Undertaker and Mankind's final one-on-one encounter was on the March 1, 1999, edition of Raw.
This was an underwhelming match between the pair. Undertaker had the upper hand and Mankind attempted to hit Undertaker with a steel chair, but it was to no avail. The match was ruled as a no contest with Undertaker attempting to attack McMahon, but Boss Man saved him from his clutches.
9 Heat (12/6/98)
The Undertaker and Mankind clashed on the December 6, 1998, taping of Heat. Steve Austin was at ringside, and Undertaker shifted his attention towards the Texas Rattlesnake. Mankind attempted to hit the Phenom with a steel chair, but the referee grabbed it from him.
Undertaker and Mankind's match on Heat was average, and it was a typical TV match. The Deadman dominated the majority of the match. However, the match came to a halt with The Rock getting involved, and all hell broke loose with Austin joining in the chaos.
8 Raw (9/14/98)
After their infamous Hell in a Cell meeting at King of the Ring 1998, The Undertaker and Mankind were adversaries once again in a No Disqualification match. Mankind came down the aisle with a sledgehammer in hand, but Undertaker had the advantage with Kane in his corner.
The Deadman was in cruise control, and he hauled Mankind into a table. Mankind rallied back, and he nailed Undertaker with a couple of chair shots. The Deadman continued to inflict more punishment on Mankind as he connected with a jaw-dropping Tombstone. The match was ruled as a no contest as The Rock interfered and prevented Undertaker from hitting Mankind with a sledgehammer shot.
7 SummerSlam 1996
Mankind and The Undertaker clashed in the first Boiler Room Brawl at SummerSlam 1996. The winner had to retrieve the urn from Paul Bearer. It was a physical brawl as expected between the pair, and they fought in an isolated room before they navigated their way into the arena.
Neither man held back, and it was an intriguing match to follow. Undertaker was going to retrieve the urn from Bearer, but Bearer refused to give it to Undertaker. Mankind went on to win this match signaling the end of Undertaker and Bearer's four-and-a-half year alliance.
6 Raw (12/9/96)
One week before The Undertaker would face The Executioner in an Armageddon Rules match, The Undertaker and his old nemesis Mankind clashed in a No Holds Barred match in the main event of the December 9, 1996 taping of Raw.
Undertaker was looking to put Mankind away early on with the Tombstone but the Executioner interfered. It was a decent match, and Mankind almost finished off Undertaker with the Mandible Claw. Nevertheless, the Phenom regrouped, and he registered another win over Mankind with a Tombstone Piledriver.
5 King Of The Ring 1996
King of the Ring 1996 was the site of Mankind and The Undertaker's first one-on-one encounter on pay-per-view. Undertaker played mind games before the match began as Paul Bearer walked down the aisle, and Undertaker took Mankind by surprise by attacking him with a flying clothesline in the ring.
Bearer distracted the referee which allowed Undertaker to hit Mankind with a steel chair. This was an excellent match and despite it not being a No Disqualification match it felt like one. Mankind recovered from a sickening chair shot to the head, and he finished off Undertaker with a Mandible Claw after Bearer accidentally clocked Undertaker with the urn.
4 Survivor Series 1996
The Undertaker and Mankind battled once again at Survivor Series 1996. Mankind's manager Paul Bearer was erected above the ring in a shark cage. This was a fantastic match and Undertaker dominated large portions of the match.
Bearer was helpless, and he couldn't do anything to help Mankind. Nevertheless, Mankind battled hard as he countered the Tombstone, and he cinched in the Mandible Claw. The Deadman didn't succumb to it, and he finished off Mankind with a Tombstone to earn another win over his rival.
3 In Your House: Revenge Of The 'Taker, 1997
The Undertaker defended the WWE Championship against Mankind at In Your House: Revenge of the 'Taker. It was the Deadman's first title defense since he beat Sycho Sid for the gold at WrestleMania 13. This WWE Championship match is often overlooked but it was another remarkable battle between the bitter enemies.
This was another violent match between the match with Mankind on the receiving end of a chair shot to the face. Mankind went through the broadcast table head first after Undertaker nailed him with the steel steps. Ultimately, Undertaker laid out Mankind with his trademark Tombstone Piledriver, and he got his title run off to a great start.
2 In Your House: Buried Alive, 1996
Mankind was seeking his third successive win over The Undertaker in the inaugural Buried Alive match. They closed out the show, and they knocked it out of the park in a superb match. There was no shortage of drama with Undertaker showcasing his tremendous athleticism by clotheslining Mankind on the outside after launching himself off the chair in the crowd.
There was a plethora of chair shots involved in this war of attrition. The battle moved towards the gravesite and Undertaker finally registered his first win over Mankind after he Chokeslammed into the grave and he buried him alive.
1 King Of The Ring 1998
Unquestionably, the greatest match in The Undertaker and Mankind's series of matches was their Hell in a Cell match at King of the Ring 1998. They wasted no time to get things underway with the battle starting at the top of the cell.
Mankind took a tremendous amount of punishment as Undertaker launched him off the top of the cell and through the broadcast table. Mankind somehow found a way to carry on and the Deadman Chokeslammed his 287-pound frame through the top of the cell which gave way. Blood was shed, and their battle moved into the ring with Undertaker wrestling with a broken ankle. Mankind went through some thumbtacks, and Undertaker sealed the deal with a Tombstone Piledriver.