The Undertaker and Mankind are two of the most legendary wrestlers of all time. Creating unique and fascinating gimmicks, putting on amazing matches, and having some of wrestling's most amazing moments.
The two men have had some amazing moments against each other throughout their careers, having had a serious rivalry throughout their runs. Putting each other through some of the most brutal matches in history in the process.
Whether it be multi-man matches, tag team bouts, or straight singles matches the two men have competed countless times. Within this list, we will take a look at the five best and worst matches against each other.
10 Best: Tag Team Buried Alive
We kickstart this list with a very crazy tag team match that utilised the buried alive stipulation. It isn't often a buried alive match takes place in WWE, let alone on a random episode of SmackDown, but that is exactly what happened here.
This match saw two popular tag teams face off for the Tag Team Titles as the Rock N' Sock Connection defended against Big Show and The Undertaker. With four very experienced main event stars, they managed to work the stipulation impressively.
In the end, Mankind and the People's Champion dropped the titles, with the power of the two bigger men proving too much.
9 Worst: Fatal Five-Way
This match saw five of WWE's most legendary names compete for the chance to become the number one contender to World Heavyweight Championship. With Undertaker facing, Mankind, Kane, Big Show, and The Rock.
This was just total utter chaos from start to finish and it actually ended in a no contest. Despite all the star power, this match just summed up the Attitude Era to perfection, which was that it was messy.
The men in the match randomly decided to attack all the referees in WWE who came down to try to officiate one after the other. This then led the entire locker room to come out as this just ended in one huge brawl rather than an actual match.
8 Best: In Your House
While The Undertaker and Mankind competed in a lot of gimmick matches throughout their careers, but that doesn't mean that they were reliant upon it. The two men also proved that they could work excellent traditional wrestling matches as well.
Their bout at In Your House: Revenge Of The Taker was perfect proof of that. Competing for World Title, the two men put on an excellent wrestling match that didn't rely upon the bells and whistles of any gimmicks.
They showed the world the chemistry that they had and simply had a fantastic in-ring wrestling match. It's a fantastic back and forth match that highlights just how great they both were during these stages of their careers.
7 Worst: Kane Imposter
During Monday Night Raw in 1998, it was revealed that The Undertaker has been dressing as Kane, being an imposter to continue the feud with his brother. Throughout that time, he ended up having a very short match with Mankind.
The two men competed on Raw, with everyone thinking it was Kane who was wrestling as the Big Red Monster picked up the win in under three minutes. While it wasn't technically a match against The Undertaker, it was Mark Calloway behind the mask.
He was revealed to be Kane and that storyline continued, which is why this makes the list. A wasted match that diminished the epic rivalry that Undertaker and Mankind had was a bad call by WWE.
6 Best: Buried Alive
Another buried alive match makes the list between Mankind and The Undertaker, only this time it was a strict singles match. With just two men they managed to make a much greater match than the tag team listed earlier.
The two men were engaged in a bitter feud at this stage of their careers and it certainly suited this stipulation. The two men battled in a very physical brawl, and the psychology involved was truly superb.
In the end, the Deadman came out on top in this one, burying Mankind to score the victory. However, this wouldn't bring an end to their feud as they competed again just a month later.
5 Worst: Handicap Bout
The Attitude Era was full of stars and because of that WWE was able to stack up Monday Night Raw with massive matches on a regular basis. However, that doesn't mean that they were always great.
Often the matches would feature lots of big names and this handicap match is an example of that. With the Brothers of Destruction teaming to take on The Rock, Ken Shamrock, and Mankind, this should have been amazing.
But with just over 10-minutes, most of the talent barely got any time inside the ring and the whole thing felt more of a rush than a classic wrestling bout.
4 Best: Boiler Room Brawl
There haven't been many boiler room brawl matches in the history of WWE, mainly because they take place backstage and they're not great for the live audience. However, when they are done right they can be amazing.
The Undertaker and Mankind competed in this stipulation in 1996 at SummerSlam and they proved just how good it can be. With a brilliant feud that dominated the summer of that year, this was just one of many great matches that they had.
Unsurprisingly, given that the stipulation has always been associated with him, Mankind earned the victory in this one. It's totally unlike any other match type, and it stood out in a good way.
3 Worst: Disqualification
For some reason, WWE made the decision to have The Undertaker take on Mankind during an episode of Sunday Night Heat back in 1998. A show that didn't usually feature mega matches like this, something seemed off right from the start.
Of course, something was off as well, with the match lasting less than five minutes as it actually ended via disqualification. This quickly turned into an angle rather than a match, making it one of the worst the two legends ever had.
2 Best: Hell In A Cell
When it comes to these two men, this is the match that everyone thinks about and there is a good reason for that. Taking place at the King of the Ring 1998 PPV, the two men created the most iconic Hell in a Cell match in history.
With Mankind being thrown off the top of the cell as JR questioned if he was dead or not being something all wrestling fans know about. That in itself would have been enough, but they then continued the match.
Being sent through the roof of the cage and then having, even more, wrestling inside the ring afterwards, Mankind went above and beyond the call of duty. They created an unforgettable match that has never been topped since, and never will in the future.
1 Worst: Count Out
A wrestling match that only lasts for three minutes and ends in a count-out is never going to be seen as a classic. The Undertaker and Mankind competing on Raw is a major match, yet WWE made this into an angle.
It is a classic decision that WWE often makes, ruining matches to further storylines, rather than just doing an angle from the starting point. The two men faced off for three minutes and it ended in a count-out.
By default, that instantly has to be considered the worst match between the two men, simply because it was an angle rather than a match. Although, it does remain a strange decision from WWE to waste a major match like this.