The Top 15 Undertaker Matches of All Time – A Retirement Look Back

The Underataker Upon His Debut - SRC WWE

With the end of the Undertaker’s in ring career, I was thinking about creating a list to commemorate his career. With that in mind, I have gone back and thought about all of the matches that he’s had on PPV and television, etc.

Here we go, there are top 10 Undertaker matches of all time. These matches are going to show you just how amazing the Undertaker was in his prime, even if his latter years suffered. These are my picks for the top 10 Undertaker Matches of all time.

Undertaker vs. Randy Orton Wrestlemania 21

I was in the building for this one. I was above the entry way at the Staples Center and it was a fun match. Randy Orton had been burying older talent, he was pushing the Legend Killer persona, and Undertaker was set to stop him. Along the way, a lot of legends tried to warn Orton, including his dad, and he wouldn’t listen. Undertaker dropped him like a bad habit in this match.

Undertaker vs. Kurt Angle Now Way Out 2006

Undertaker against Kurt Angle was a hard hitting, diverse wrestling match. A good overall push forward in this one, which is grand. Kurt Angle really put the boots to Taker here, and Undertaker was selling like crazy for the Olympic Gold Medalist. 2006 seems so far away, and these two put on a show.

Undertaker vs. Rob Van Dam Vengeance 2001

Rob Van Dam was great here, and Undertaker respected the athleticism that Van Dam had. This was a better match than I thought, and Rob didn’t just roll through Undertaker at all. Van Dam took a lot of offense, and Undertaker pushed through a great deal of his moves too.

Undertaker vs. Triple H Hell In A Cell Wrestlemania 28

Triple H and Undertaker put on a show in this one, and it was a great one. I liked this better than their match at X-7. This was a better fought battle, Shawn Michaels helped, and yet Triple H just couldn’t beat Taker. I loved it. You loved it, go back and watch this one.

Undertaker vs. Brock Lesnar Hell In A Cell No Mercy 2002

This match, in 2002, was great. I was at Unforgiven where these two fought to a disqualification finish, and that was fun. But it was this match that really made the feud great. Taker and Lesnar in their prime, and it was great to see the two put on a seriously heavy hitting match. These guys pulled out all of the stops for the match, and it still lives up if you ask me.

Undertaker vs. Mankind (Buried Alive Match) In Your House Buried Alive 1996

Mankind was the one major character that had been introduced that had Undertaker’s number. In this match, they introduced the Buried Alive concept. Mankind lost this one, but after the initial loss, the heels in WWF at the time came out and buried Undertaker completely. It was great overall.

Undertaker vs. CM Punk Wrestlemania 29

This should have been the main event. CM Punk and Undertaker tore the house down in my book. Punk going one on one with the best striker in WWE was great, and Taker didn’t let up. Punk and Undertaker fought before, but last time they met was a burial. This was incredible, and went back and forth, great solution overall.

Undertaker vs. Bret Hart vs. Stone Cold Steve Austin vs. Vader In Your House Final Four 1997

If you have ever seen the Royal Rumble 1997, you know that there was a lot of issues at the end. That led to this incredible 4 way match, with lots of brawling, lots of technical elements, and brutal chair shots. Hart and Stone Cold would put themselves through the fire in this one, and Undertaker would continue to go to Wrestlemania. This was great. If you haven’t seen this, you’re missing out on a great 4 way match.

Undertaker vs. Stone Cold Steve Austin (WWF Title Match) In Your House Cold Day In Hell 1997

One of my personal favorite matches, Stone Cold nearly won this match if it wasn’t for Brian Pillman. Undertaker was on a streak in 1997, defending the title against a lot of guys in 1997 before dropping the belt to Hart at Summerslam. If you haven’t seen this one, it’s a great one, and both guys were in their absolute prime. No injuries, no nothing, just great wrestling.

Undertaker vs. Shawn Michaels Hell In A Cell Match In Your House Badd Blood 1997

Shawn Michaels and Undertaker started on a collision course at In Your House Break Down, and this really put on a showcase. This was the first Hell in A Cell and it is one of the best matches ever. The two really put on great fighting, great wrestling, and psychology. This saw the debut of KANE.

Undertaker vs. Edge (WWE Tittle Match) TLC Match One Night Stand 2008

Edge and the Undertaker had a lot of matches, but this is the one that stands out for me. The main reason why is because The Undertaker gets dropped through a 3-tiered set of tables. It is an impressive fall and it was fun to watch overall. The TLC option was great here, and Edge really did great against the phenom.

Undertaker vs Jeff Hardy (WWE Title Match) Ladder Match Monday Night Raw July 1, 2002

Undertaker and Jeff Hardy? Yes. Undertaker hit Jeff with the hardest hits you’ve ever seen. Including some of the most brutal chair shots. When Undertaker won the match, and Hardy got back up, the crowd went nuts and Undertaker shook his hand, hugged him, and told him he got his respect. In the back, it was the same, Undertaker gave Jeff Hardy his best, and would lobby for him, because he took on some serious hits in this match. Hardy was the real deal here.

Undertaker vs. Hulk Hogan (WWF Title Match) Survivor Series 1991

The biggest match for Undertaker since his initial debut had a lot of people crying. Grown men and children were crying because Hulk Hogan had been made to look weak. Undertaker gave Hogan a tombstone on a chair, and won the title! This was huge in 1991.

Undertaker vs. Shawn Michaels Wrestlemania 25

The better match between the two if you ask me. Undertaker was great, and Michaels did a great job against him as well. This was so good, you should see it three or four times. These two put on the best match I’ve seen in a long time.

Undertaker vs. Bret Hart (WWF Title Match) Summerslam 1997

The number one match in the Undertaker’s career, according to me, is simple, Summerslam Hart and Soul. This was the best match that you can see if you have never seen an Undertaker match. Bret Hart put on a showcase of greatness, with Undertaker giving his best too. Shawn Michaels was the guest referee, and the ending was absolutely insane. This was so good, that when the initial broadcast was pushed through, I saw this one twice. That’s right, I saw the replay and the regular event!

That’s it. I hope that Mark aka The Undertaker has a good retirement. He has put in some great work, if you ask me.