World Wrestling Entertainment

The List: Undertaker's Best Matches

November 24, 2020

By Ryan Satin 

With The Undertaker officially retiring from in-ring competition this weekend, I gathered some of The Deadman's best matches to help commemorate his legacy.

Look, I realize making a list of The Undertaker’s best matches in actual definitive order is nearly impossible. There are a plethora of options to choose from, and every fan’s opinion will vary.

Therefore, in the interest of fairness, I consulted with the smartest wrestling fans possible – aka the people who follow me on Twitter and my friends/coworkers – to make this list as “fair” as possible.

Now that we’ve got that out of the way, here’s what I came up with:

10) vs. Jeff Hardy on Raw – Ladder Match 

Personally, I didn’t enjoy this match.

But that’s an entirely different column for another time. 

For now, I’ll just leave it here since so many of you on Twitter included it as one of your favorite Undertaker matches. 

9) vs. AJ Styles at WrestleMania 36 

The Undertaker’s final match in cinematic form. 

After years of searching for the perfect ending to his career, this match finally sealed the deal and deserves some praise on a list of his best matches.

8) vs. CM Punk at WrestleMania 29

A classic match that had a nearly perfect build. 

Punk and Taker definitely stole the show that night.

7) vs. Kurt Angle at No Way Out ’06

When I asked Twitter for their favorite non-WrestleMania or Hell in a Cell match involving The Undertaker, this one received the most votes.

After rewatching it today, I remembered why it’s so beloved.

6) vs. Kane at WrestleMania 14 

The first in-ring encounter between Kane and Undertaker is a must-watch for any wrestling fan.

Undertaker made his "brother" look like an absolute monster.

5) vs. Triple H at WrestleMania 28 – Hell in a Cell

The Undertaker had incredibly high expectations to live up to when he faced-off against Triple H at WrestleMania 28.

Following the success of his WrestleMania matches against Shawn Michaels, which led to HBK’s retirement, Undertaker was targeted by Triple H with determination to end the streak.

This led to another wrestling masterpiece between the two at WrestleMania 27 in 2011. 

Their Hell in a Cell match with HBK as guest ref one year later, though, dubbed “The End of an Era” marked the closing chapter on a set of unforgettable matches between three of the all-time best.

At the time, I didn’t believe this would truly be the “End of Era” as advertised. I knew we’d still see Undertaker and Triple H on WWE TV, so my young mind couldn’t quite grasp what it meant.

Watching it back in 2020, though, there’s no doubt this was truly the end of an era that will be difficult for anyone to match.

4) vs. Stone Cold Steve Austin at SummerSlam ’98

SummerSlam ’98 was peak Attitude Era. 

Instead of me explaining the background to the main event, just watch the promo video perfectly set to “Highway to Hell” to get hyped all over again (or maybe for the first time).

When Stone Cold and Undertaker faced-off in the main event of this show, the crowd was already at a fever pitch, but their intensity in the ring took things to the next level.

Each part of the match felt like a real fight between two badasses.

Something you’ll notice in watching this match was the expert way in which these two wrestlers had the crowd in the palm of their hands.

The psychology at play throughout made fans yearn for Stone Cold to finally hit a Stunner on his opponent. When he finally does, it receives the sort of pop most wrestlers would kill for.

If you’re a younger fan who has never seen this match, do yourself a favor and watch it from bell to bell. 

If you’ve already seen it, go watch it again. 

Regardless, you’ll thank me later.

3) vs. Shawn Michaels at Badd Blood ’97 – Hell in a Cell 

The first Hell in a Cell match was wild.

Over a decade before their iconic performances at WrestleMania, Undertaker and Shawn Michaels introduced one of WWE’s most intense match concepts at Badd Blood and set the standard for what it would become.

Two top guys putting it all on the line in brutal fashion to finally end the most bitter of feuds. 

The inaugural cell match also featured the debut of Kane. 

This was arguably one of the best debuts in WWE history and led to one of the company’s most legendary rivalries.

Considering it all got started in this match, a gimmick that has gone on to become it’s own pay-per-view event each year, you can’t make a list of best Undertaker matches without including it. 

2) vs. Mankind at King of the Ring ’98 – Hell in a Cell

Wrestling purists might argue otherwise here, but Undertaker’s second Hell in a Cell encounter against Mankind is one of the most memorable matches in WWE history. 

To this day, Undertaker and Mick Foley continue to be asked about it since the moment is so ingrained in people’s minds.

“The Deadman” tossing another man off a steel structure from that high in the air, as well as chokeslamming him through the top of the cell, looked like you were watching a murder on pay-per-view. 

This made Mankind an instant star and caused many new fans to start watching the product.

Personally, this was the match that made me a fan for life. 

I finally had something I could show people to prove them wrong when they called wrestling “fake.”

Even now, when a non-wrestling fan asks me to show them a match that will get them to believe, this is what I put on because it’s impossible to not get sucked in.

Foley’s resilience mixed with Undertaker’s willingness to continue doling out punishment makes anyone watching believe that what they are seeing isn’t scripted entertainment. 

When you can do that, pro wrestling is at its best.

1) vs. “The Heartbeak Kid” Shawn Michaels at WrestleMania 25 

What can you say about this match that hasn’t already been said?

The epic encounter between these two icons will arguably go down as one of the greatest wrestling matches of all-time.

Going into the match, Taker had never defeated Shawn Michaels on pay-per-view, making HBK his toughest challenger yet when it came to keeping his WrestleMania streak intact.

This set the stage for a master class in pro wrestling from two legends working at a level most will never rise to.

It’s impossible to watch this match and not get hyped. 

The roar of the crowd during each near fall. The intensity from both Superstars. The psychology.

It was all perfect.

The fact that they were able to do it again the following year and produce a match on the same level is one of the most remarkable accomplishments in WrestleMania history.


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