The Undertaker’s 10 Best Matches

With WWE‘s highly-acclaimed series on The Undertaker (The Last Ride) wrapping up this weekend, all eyes and minds are on the career of one of the biggest legends in the history of professional wrestling. Having first entered the WWE in 1990, Taker has had one of the longest careers in the history of the company, and over the years he has had countless great matches and memorable feuds. Trying to narrow that list of matches down to ten is a tough task, but that’s what we have set out to do today.

One thing that is for sure, there’s a certain “Showstopper” who stands out as Taker’s greatest opponent, and the story of their careers (and how they failed to intersect for a long time) makes that particularly remarkable. We’ll get into that more in a moment.

So as The Undertaker continues to ponder the eventual end of his in-ring career, as we’ve seen play out on The Last Ride, come along with us as we look back at that career with ten of the “Dead Man’s” greatest matches. The matches are presented in chronological order.

Undertaker vs. Shawn Michaels (Badd Blood In Your House 1997)

One of the things that makes The Undertaker’s matches with Shawn Michaels so surprising is how long it took for them to finally have an in-ring feud. While 1997 might seem like a long time ago in 2020, back then it was remarkable that WWE had kept Taker and Michaels away from each other for the better part of seven years. Can you imagine that happening today?

They first collided on PPV at Ground Zero In Your House, one month after HBK cost Taker the WWE title in a SummerSlam match with Bret Hart (Shawn was the guest referee and inadvertently hit Taker with a chair). The Ground Zero match was followed up by the first-ever Hell In A Cell match at Bad Blood In Your House in October. In terms of the feud the two had, and the wild match at Ground Zero, it made sense to introduce the structure for this one. The winner would receive a title shot against Bret Hart at Survivor Series in Montreal the following month, bringing things full circle from where the story began at SummerSlam.

In my opinion, this still ranks as the greatest Hell In A Cell match in history, which is a true testament of the bout considering it was the first one and there was no blueprint. This is Michaels at his bumping-all-over-the-place best, while The Undertaker plays the perfect foil as the direct opposite of Michaels: a slower, plotting, big man with the power to overcome the more agile and faster opponent. 

The finish of the match saw the debut of another star who would play a major role in Taker’s career moving forward: Kane. 

Undertaker vs. Kurt Angle vs. The Rock (Vengeance 2002)

Here we enter the “Biker Taker” era. Angle and Taker always had great chemistry together, and when you add in The Rock, this one really becomes spectacular. The Undisputed Title was up for grabs on this night in July 2002. Taker walked in champion, but The Rock walked out with the belt and set the stage for a memorable encounter with Brock Lesnar the following month at SummerSlam. 

By this point, Rock was already becoming a Hollywood star but came back for this short but memorable run. Despite having been in WWE for 12 years at this point, this was only Taker’s fourth world title reign (he defeated Hulk Hogan for the belt at May’s Judgment Day) and it came to an end on this night.

 

Undertaker vs. Brock Lesnar (No Mercy 2002)

Two months after winning his first world title from The Rock at SummerSlam, Lesnar entered the fabled Hell In A Cell with The Undertaker. This is the second of four Hell In A Cell matches on this list, making it easily the signature match in the career of the “Dead Man.”

While Undertaker and Lesnar would have countless matches over the years, many of them great, this one stands the test of time as the best. Surprisingly, they even had an outstanding Hell In A Cell match together at the PPV of the same name as recently as 2015. However, the 2002 match at October’s No Mercy remains their all time best bout together. 

Undertaker vs. Randy Orton (WrestleMania 21)

I would argue this was Undertaker’s first truly great WrestleMania match (some would go with his match against Triple H at 17, though I find it a tad overrated). By this point, “The Streak” was established and Orton had developed his reputation as “The Legend Killer.” Who better to take on than one of the sport’s ultimate legends at the biggest show of the year?

Once again, just as when he feuded with Michaels, when you put Undertaker in the ring with a smaller and more agile opponent you get something particularly memorable. Undertaker kept up with the younger Orton and had a really good outing on this night in Los Angeles. Oh, and The Streak remained intact. 

Undertaker vs. Edge (WrestleMania 24)

This was the only time that Edge headlined a WrestleMania, and it sometimes gets lost in lists looking back at Taker’s best matches because of what came the next two years against Shawn Michaels. However, this one certainly holds up 12 years later. 

At the time, this was one was neck and neck with the WrestleMania 21 match against Orton and a battle with Batista the previous year as Taker’s greatest WrestleMania match. While Taker’s career was never known for championship reigns (simply put, he just didn’t need the title), it was cool to see him win the world title at Mania for the second consecutive year (and third time ever). 

Undertaker vs. Edge (SummerSlam 2008)

From the very first match in 1997 all the way up through another classic encounter with Brock Lesnar in 2015, The Undertaker was always spectacular in the Hell In A Cell. Heck, four of the top ten matches on this list are Cell matches. Taker and Edge followed up their classic at WrestleMania in 2008 with another classic at the second biggest show of the year, SummerSlam. This time inside of the fabled cage.

This one sometimes isn’t talked about as much as their WrestleMania match but is actually, in my opinion, an even better match. It is 100% Taker’s greatest SummerSlam match. Check it out. 

Undertaker vs. Shawn Michaels (WrestleMania 25)

Taker and Shawn rekindled their feud from the 1990s by facing off for the first time at WrestleMania in their home state of Texas. It’s hard to think of anything to say about this one that hasn’t already been said: it’s easily a top five WrestleMania match of all time, with many believing it is the best. 

At the time, what really stood out about the match was all of the false finishes and kick-outs following finishing moves. While that’s more common place today (perhaps even too common), back then it was more unique and had the fans on the edges of their seats in Houston. It was a true roller coaster that set the stage for the following year. 

Undertaker vs. Shawn Michaels (WrestleMania 26)

It’s hard to imagine any match topping what the two did at WrestleMania the previous year in Houston, but they may have done that the following year in Arizona. Fans are truly split on which of the two matches was better, but in the end it doesn’t really matter. Both stand the test of time as two of the all time greatest matches in WrestleMania history.

This time out, the story was different. Michaels put his career on the line to see if he could finally be the person to end the Streak. The storyline build to this one might have been better than the previous year, though the actual match may have been better one year earlier as it was more original at the time.

As we all know, Michaels lost and retired (until he came back for a match in Saudi Arabia in the fall of 2018). As we’ve seen play out on The Last Ride, Taker is somewhat envious to how HBK was able to walk away from the ring after this match and have a nice ending to his career. 

Undertaker vs. Triple H (WrestleMania 28)

The “End of an Era” match and what concluded a four year story with Shawn Michaels and his best friend Triple H taking on the Undertaker. After Shawn’s two losses at Mania 25 and 26, Hunter came out to try to do what Shawn couldn’t at WrestleMania 27. Spoiler alert: he didn’t.

They followed it up at WrestleMania 28 by bringing back Michaels as a special guest referee, this time locking them all up in a Hell In A Cell. The crowd was totally invested throughout as The Streak seemed in danger, especially with HBK as the referee. The near falls during the match make the crowd go absolutely bonkers, and we get one of the more memorable post match send-offs in WrestleMania history to cap it all off. 

Undertaker vs. CM Punk (WrestleMania 29)

The build to this match became controversial when Punk introduced an urn with the “ashes” of Taker’s former manager Paul Bearer (who had recently passed away), but the match itself isn’t controversial in that it absolutely delivered. 

This was Punk’s last WrestleMania match (as of now), and what a way to go out. The build to the match, rightly or wrongly, will always be memorable for its controversy, but the match once again shows that Taker often did his best work against smaller and more undersized opponents (Punk, Michaels). 

Other matches that just missed the list:

• Undertaker vs. Mankind (King of Ring 1998): The iconic Hell In A Cell match is famous for two big spots. There’s no denying the fame of the match, but ring work wise, doesn’t stack up to the other matches on this list. 
• Undertaker vs. Bret Hart (SummerSlam 1997): The match is a little bit too long but a solid contest with an incredible ending
• Undertaker vs. Triple H (WrestleMania 27): Not quite as good as their match at 28, but a really good one none the less. 
• Undertaker vs. Kurt Angle (SmackDown, September 2003): They had several singles matches over the years, but this might be the best. 
• Undertaker vs. Shawn Michaels (Ground Zero In Your House): The first major PPV match between the two legends and a great outing that set the stage for the first-ever Hell In A Cell match.

What did you think of this list? Let us know in the comment section below, give me a shout on Twitter @ryandroste, and subscribe to my podcast Top Rope Nation where we will be holding a fantasy draft of The Undertaker’s best matches on the show this week.