Who Was The Undertaker’s Greatest Rival?

The Undertaker

This piece was originally written during our ‘Undertaker Weekend’ in June 2020. We are republishing this ahead of Undertaker’s ‘Final Farewell’ at Survivor Series.

The Undertaker has had a storied 30 year career in the WWE. Many points of his career have been tackled this week by the HOW staff. But today I plan on tackling a question I’m sure many people have their own answer for when it comes to The Undertaker and his career.

Who is the Undertaker’s greatest rival of all time?

The Undertaker has had battles with many WWE legends over the course of his career. And quite honestly, it was tough to go through and pick out a top one for this list. But I’ve gone through and put together this list that I think shows who exactly was the Undertaker’s greatest rival in WWE history.

Honorable Mentions

The Undertaker Vs Kane


Yes, Kane does not find his way to the podium on my list. You may not agree with me, but I’m the one writing this piece and not you.

There is no denying the history that The Undertaker and Kane have. Kane had one of the best debuts in the history of wrestling at Bad Blodd. And the build up to the first Undertaker vs Kane match was well done. But after that? Nothing really memorable happens in my opinion.

Once the build to the first match ends, the Undertaker and Kane are simply tied together because they are brothers in storyline. They go back and forth between teaming up and facing off throughout the Attitude Era. Then in the 2000s it is the same thing. Kane and Undertaker feud, then team up together later on.

But does anything memorable come from these two after the first match? My simple answer is no. The matches aren’t all that good or memorable. The Kane and Undertaker story is simply one of two guys who have history so they can feud up or have a storyline every so often.

Stone Cold Steve Austin

The Undertaker and Steve Austin had a rivalry that lasted almost the entire Attitude Era. Austin received a title shot against Undertaker at the In Your House: Cold Day in Hell PPV in 1997. While their next encounter wouldn’t take place until 1998, it was the first of many.

They briefly held the tag titles in 1998 before facing off against each other at SummerSlam of that year. They would then spend the next few months of 1998 feuding, with it later being revealed that Undertaker and Kane were working together with Vince McMahon to try and get the WWF title off Austin.

The problem was this lead to a handful of confusing and non finishes, including a double pin by Kane and Undertaker on Austin and Austin being the special referee for another match between these two and declaring himself Champion at the end.

In 1999 Austin would restart his feud with Undertaker, this time with Undertaker as the leader of the Ministry of Darkness/Corporate Ministry. Undertaker would win the WWF title from Austin then lose it back to him at Fully Loaded 1999 (a show I was at).

While the feud lasted a strong portion of the Attitude Era, it isn’t really remembered as one of Undertaker’s top feuds. Both men had better rivalries with other wrestlers during their time in the WWE.


As I mentioned on the Hot Tag Wrestling Podcast this week, The Undertaker didn’t have a great set of feuds upon his return in 2004. Outside of Randy Orton, Undertaker was stuck with the likes of JBL, Heidenreich, the Dudley Boyz, Muhammed Hassan and The Great Khali. Yuck.

But The Undertaker then won the 2007 Royal Rumble and challenged Batista for the World Heavyweight Championship at Wrestlemania 23. The match was great and over shadowed the main event of the night which was John Cena vs Shawn Michaels. Think about that, another match out shined a Shawn Michaels match at Wrestlemania.

Undertaker and Batista went on to have a handful of matches over 2007 that I believe helped reignite his run as the Deadman. Sometimes two wrestlers just have great chemistry together. Batista and Undertaker had just that.

But while all of these matches were good, again, both men had more memorable rivals during their careers.


Batista and The Undertaker dominated 2007 on Smackdown. Edge and Undertaker dominated 2008.

Edge rounds out the last of our honorable mentions. One of my favorite things about the Edge/Undertaker rivalry is that we got an Undertaker TLC match out of it. I’m glad Undertaker got two good rivalries that lasted almost an entire year after the crap he was handed when he first came back in 2004.

Similar to Batista, Edge just had a great chemistry with the Undertaker. Overall I think I prefer Batista’s matches but the Edge ones are a very close second from this time frame of the Undertaker. If for some reason you still didn’t take Edge as a credible main eventer before this feud, you almost had to take him seriously after it.

The Podium

3. Shawn Michaels

The Heartbreak Kid comes in third when it comes to the Undertaker’s greatest rivalries. These two first started going up against each other in 1997. Shawn Michaels cost Undertaker the WWF title at SummerSlam. They then went on to main event the next two In Your House PPVs, with the second being the memorable Hell In A Cell match. It finished at the 1998 Royal Rumble when Shawn Michaels beat Undertaker in a casket match.

These two really wouldn’t cross paths again until the 2007 Royal Rumble when they were the last two wrestlers in the Rumble match. The mini match they had as the last two entrants was great. The next year they would start the 2008 Royal Rumble.

In 2009 Undertaker and Shawn Michaels fought at Wrestlemania XXV in what many consider the greatest Wrestlemania match of all time (it is number two for me after Austin/Bret). And then the next year at Wrestlemnia 26, both men fought again after Shawn Michaels agreed to put his career on the line. Undertaker won, and we never saw Shawn Michaels wrestle again. No matter what anyone says, Shawn Michaels never wrestled another match in the WWE. Just like Rocky 5 never happened.

So why does this come in at #3 after I just praised all of their matches? Well, for me, while Michaels did have the best matches with Undertaker throughout Taker’s career, their rivalry was a very short one. I wouldn’t even consider their Wrestlemania matches a rivalry. I would say they are two matches between two top stars in the company. Like a spectacle match more than a rivalry.

2. Mankind

When I was a kid watching the WWF in the mid 1990s, I was made to believe that Undertaker was unstoppable. He would always get the best of his opponent in the long run even if there were a few hiccups along the way.

Then came Mankind. Mankind debuted and immediately went after Undertaker. And he got the best of the Undertaker at every turn during the summer of 1996. It was something you never saw with an Undertaker program. For months Mankind stood tall over Undertaker.

And if that didn’t lead you to believe Mankind was a force, taking Paul Bearer away from the Undertaker definitely did. Paul Bearer helped Mankind win the Boiler Room Brawl and also the Buried Alive Match.

The feud died down at the end of 1996 but was always brought back from time to time. Undertaker’s first title defense after Wrestlemania 13 was against Mankind. And of course it was brought back at King of the Ring 1998 with the famous Hell In A Cell match.

Undertaker did a great job of establishing Mankind as an immediate threat to the viewers of WWF. That is something you do not see today. No one got the better of Undertaker at the time like Mankind did. And if you asked me it helped Mankind/Mick Foley later in his career.

1. Brock Lesnar

When I was making this list, I knew it was going to come down to either Mankind or Brock Lesnar for the top spot. After much deliberation in my head, I came to the conclusion that Brock Lesnar is the Undertaker’s greatest rival?

First off, these two always had hard hitting matches with each other. Even in 2016 (Wrestlemania match aside) their matches looked brutal every time.

Brock Lesnar was on the rise in 2002 and after he beat The Rock for the WWF title at SummerSlam, his first major opponent was the Undertaker. At the time, Taker was on his Big Evil respect phase of Biker Taker. And what better way to get Brock Lesnar over as a major star than to have his first post title win feud with the man that was considered the measuring stick in the WWF at the time. Their Hell In A Cell match at No Mercy that year remains one of my favorite Cell matches. Brock always got the best of the Undertaker. Even in the 2003 Royal Rumble, Brock eliminated Undertaker to win it.

Then comes The Streak. I can’t hold that match against either guy because of the concussion Undertaker suffered during the match. Had that not happened, who knows what kind of match we could have gotten. But they rebounded pretty well with two good matches in 2015 to make people forget about that match.

Brock Lesnar always got the best of Undertaker, to the point where Undertaker had to cheat and use heel like tactics to finally beat Brock Lesnar at SummerSlam. Brock won the rubber match inside of another great Hell In A Cell match.

So why does this beat out Undertaker’s rivalry with Mankind? For starters, the matches were better. Another case of two guys having great chemistry with one another. All of their matches looked vicious and brutal.

Not only that, but we had to see Undertaker cheat and break his normal ways he is remembered for to finally beat Brock. Brock always got the better of Taker and he had to use the strategies of cowardly heel to finally beat him.

And just like Mankind, Brock Lesnar was elevated by his feud with the Undertaker. Brock was firmly established as the next big thing after his feud with Undertaker in 2002. While Mankind was an established threat, he didn’t reach super stardom because of the Undertaker. Brock Lesnar did.

So do you agree? Who do you think is the greatest rival to the Undertaker?