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The Undertaker's Definitive 10 Best WWE Matches, Ranked

The Undertaker is one of the biggest legends in WWE history. From the moment he first made his iconic debut at Survivor Series 1990, fans knew 'The Deadman' would make an impact on the wrestling business. There had never been someone quite like Undertaker, and there probably never will.

10 Best Matches Of The Undertaker's WWE Career (That Weren't At WrestleMania) Featured Image
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10 Best Matches Of The Undertaker's WWE Career (That Weren't At WrestleMania)
The Undertaker became a huge WWE legend thanks to his WrestleMania Streak. However, The Deadman also had great matches at other events.

Throughout his historic 30-year career in WWE, The Undertaker went one-on-one with pretty much every top name that worked for the company during that time. Undertaker had some of the best matches in WrestleMania history, but he also had some classics on other shows. These are Undertaker's ten best WWE matches, ranked.

10 The Undertaker Vs. CM Punk (WrestleMania 29)

Overall Rating From TheSportster: 9/10

Storytelling

2.25/2.5

Technical Ability

2.25/2.5

Character Work/Psychology

2.25/2.5

Crowd Reaction

2.25/2.5

  • Dave Meltzer's Rating: 4.5 Stars
  • Cagematch.net Rating: 9.03

Undertaker became a part-time wrestler in the early 2010s, but that didn't stop 'The Deadman' from having some fantastic matches in the beginning of the decade. In 2013, Undertaker defended his WrestleMania Streak against the man who'd recently been WWE Champion for 434 days, CM Punk. Both men made spectacular entrances that night, and absolutely stole the show once the bell rang.

Some of the highlights included Punk hitting a flying elbowdrop on the announce table, 'Taker sitting up while Punk had the Anaconda Vice locked in, and Punk hitting the GTS only for Undertaker to bounce off the ropes and hit a shocking Tombstone. It was a phenomenal match that saw Undertaker pick up the final win in the history of his Streak.

9 The Undertaker Vs. Mankind - Hell In A Cell Match (King Of The Ring 1998)

Overall Rating From TheSportster: 9/10

Storytelling

2.5/2.5

Technical Ability

1.5/2.5

Character Work/Psychology

2.5/2.5

Crowd Reaction

2.5/2.5

  • Dave Meltzer's Rating: 4.5 Stars
  • Cagematch.net Rating: 9.22

One of Undertaker's best rivals was, unquestionably, Mick Foley. The latter went after 'The Deadman' as soon as he made his WWE debut in early 1996, leading to several matches that year. While those were great bouts, they didn't come close to the one they'd have two years later. 'Taker and Foley met in only the second Hell in a Cell Match on a WWE PPV at King of the Ring 1998.

While the match was far from being technically flawless, that's not what this one was about. The bumps Foley took were absolutely insane, particularly when he got tossed off the cell all the way to the announce table below. Mick nearly died when he got chokeslammed through the roof all the way to the ring, a spot that wasn't supposed to happen. Thumbtacks came into play as well in this barbaric match won by Undertaker.

8 The Undertaker Vs. Edge - World Heavyweight Championship (WrestleMania 24)

Overall Rating From TheSportster: 9.25/10

Storytelling

2.25/2.5

Technical Ability

2.25/2.5

Character Work/Psychology

2.5/2.5

Crowd Reaction

2.25/2.5

  • Dave Meltzer's Rating: 4.25 Stars
  • Cagematch.net Rating: 8.96

Edge and Undertaker began their rivalry way back in May 2007, when Edge cashed in Money in the Bank on 'The Phenom' right after he'd defended his World Title against Batista inside a steel cage. Edge got injured a few months later, but he came back at Survivor Series to cost 'Taker a Hell in a Cell Match against Batista, resuming their feud.

Edge would recapture the World Title in December, while Undertaker won SmackDown's Elimination Chamber at No Way Out 2008 to set up the main event of WrestleMania 24. They had a fantastic bout where Edge tried everything he could to end the Streak. He nearly got the win after a Spear, but Undertaker found a way to lock in the Hell's Gate submission to become the new champion.

7 The Undertaker Vs. Edge - Hell In A Cell Match (SummerSlam 2008)

Overall Rating From TheSportster: 9.25/10

Storytelling

2.5/2.5

Technical Ability

2/2.5

Character Work/Psychology

2.5/2.5

Crowd Reaction

2.25/2.5

  • Dave Meltzer's Rating: 4.5 Stars
  • Cagematch.net Rating: 9.18

Their feud would continue after WrestleMania, with Edge's then-wife Vickie Guerrero (the SmackDown General Manager) stripping Undertaker of the title after she made the Hell's Gate illegal. Undertaker went on a brief hiatus shortly thereafter, coming back in time for SummerSlam where he took on 'The Rated-R Superstar' in a Hell in a Cell Match.

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The match was unfairly hated at first due to bad timing, since it came a month after WWE became PG and thus it lacked blood and the viciousness of previous ones. However, the wrestlers gave it their all and proved a Hell in a Cell Match could still work under the restrictions of the PG Era. This is one of those matches that get better with time.

6 The Undertaker Vs. The Rock Vs. Kurt Angle - WWE Undisputed Championship (Vengeance 2002)

Overall Rating From TheSportster: 9.25/10

Storytelling

2.25/2.5

Technical Ability

2.5/2.5

Character Work/Psychology

2.25/2.5

Crowd Reaction

2.25/2.5

  • Dave Meltzer's Rating: 4.5 Stars
  • Cagematch.net Rating: 8.77

Undertaker's very last reign as WWE Champion happened way back in 2002, with 'Big Evil' beating the legendary Hulk Hogan for the gold at Judgment Day. While he had better runs with the title in the past, his best WWE Title defense came during this reign - against The Rock and Kurt Angle in a triple threat match at Vengeance 2002.

The three legends threw everything at each other and delivered one of the best triple threat matches of all time that night. Fans couldn't believe when they saw the three wrestlers stealing each other's finishers, with The Rock ultimately coming out on top. 'The Great One' hit the Rock Bottom on Angle, with Undertaker making the save less than a second too late. An absolutely breathtaking matchup.

5 The Undertaker Vs. Kurt Angle - World Heavyweight Championship (No Way Out 2006)

Overall Rating From TheSportster: 9.5/10

Storytelling

2.25/2.5

Technical Ability

2.5/2.5

Character Work/Psychology

2.5/2.5

Crowd Reaction

2.25/2.5

  • Dave Meltzer's Rating: 4 Stars
  • Cagematch.net Rating: 9.18

From a technical standpoint alone, this might very well be Undertaker's best in-ring performance ever. 'The Phenom' challenged Angle for the World Heavyweight Championship at No Way Out 2006, and the two delivered one of the best matches in the entire history of the Big Gold Belt in WWE.

They took their time at first since it was a 30 minute match, with Undertaker selling the leg brilliantly while Angle viciously went after said body part. Their sequences and reversals were amazing, especially in the last 10 minutes. Angle found ways to turn the Chokeslam, the Last Ride and the Tombstone into the Ankle Lock, but 'The Deadman' wouldn't quit. 'Taker eventually locked in the Hell's Gate, and Angle was able to roll through into a bridge pin for the clean victory.

4 The Undertaker Vs. Triple H - Hell In A Cell Match (WrestleMania 28)

Overall Rating From TheSportster: 9.75/10

Storytelling

2.5/2.5

Technical Ability

2.25/2.5

Character Work/Psychology

2.5/2.5

Crowd Reaction

2.5/2.5

  • Dave Meltzer's Rating: 4.75 Stars
  • Cagematch.net Rating: 9.23

Four of the best matches of Undertaker's career happened at WrestleMania between 2009 and 2012, with 'The Deadman' successfully defending his Streak against both Shawn Michaels and Triple H (twice). The final match of that saga happened at WrestleMania 28, was billed as "the end of an era" and it featured HBK as the special referee inside Hell in a Cell.

Undertaker Triple H Shawn Michaels Wrestlemania 28
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Needless to say, it was truly the culmination of an epic story. Even with the epic confrontation between The Rock and John Cena, this was the true show stealer. The match had some iconic nearfalls that will be remembered forever, especially Undertaker kicking out of the Superkick/Pedigree combo. It was one of the best matches in the careers of both legends.

3 The Undertaker Vs. Shawn Michaels - Hell In A Cell Match (In Your House: Badd Blood 1997)

Overall Rating From TheSportster: 9.75/10

Storytelling

2.5/2.5

Technical Ability

2.25/2.5

Character Work/Psychology

2.5/2.5

Crowd Reaction

2.5/2.5

  • Dave Meltzer's Rating: 5 Stars
  • Cagematch.net Rating: 9.53

Years before The Undertaker and Shawn Michaels wrestled at back-to-back WrestleManias, they made history by competing in the first Hell in a Cell Match ever. At In Your House: Badd Blood 1997, the two men laid the foundation for all the future Hell in a Cell matches, just like the ones already mentioned throughout this article.

Undertaker absolutely destroyed Michaels from pillar to post for much of this match, wanting to make HBK pay for costing him the WWE Championship at SummerSlam. However, the debuting Kane memorably forced his way into the cell in the bout's final minutes, confronting his brother and delivering a Tombstone that allowed Shawn to win.

2 The Undertaker Vs. Shawn Michaels (WrestleMania 25)

Overall Rating From TheSportster: 9.75/10

Storytelling

2.25/2.5

Technical Ability

2.5/2.5

Character Work/Psychology

2.5/2.5

Crowd Reaction

2.5/2.5

  • Dave Meltzer's Rating: 4.75 Stars
  • Cagematch.net Rating: 9.61

Most fans probably don't know (and those who do know, would love to forget!) that WWE actually considered ending the Streak in 2009 at the hands of... Vladimir Kozlov. 'The Deadman' himself recently told this story in an interview with Ariel Helwani. Thankfully, the company realized it would be a terrible idea and booked 'Taker in a matchup against Shawn Michaels instead.

The two delivered a fantastic match at the 25th edition of WrestleMania - one that is considered the best match of all time by many fans. The only thing that lacked was a strong story since it happened at the last minute, but it was perfect in every other aspect. The finish, with Undertaker catching Michaels on a moonsault attempt before delivering the Tombstone Piledriver, was flawless.

1 The Undertaker Vs. Shawn Michaels - Streak Vs. Career (WrestleMania 26)

Overall Rating From TheSportster: 10/10

Storytelling

2.5/2.5

Technical Ability

2.5/2.5

Character Work/Psychology

2.5/2.5

Crowd Reaction

2.5/2.5

  • Dave Meltzer's Rating: 4.75 Stars
  • Cagematch.net Rating: 9.53

Unlike the year before, Michaels vs. Undertaker at WrestleMania 26 had one of the best storylines of any 'Mania main event. Michaels desperately put everything on the line just for another chance to end the Streak, including his own entire career. This really put Undertaker over as WWE's ultimate boss, and it guaranteed history would be made in the end - either the end of a legendary career, or the end of the legendary Streak.

Fans were on the edge of their seats throughout the entire match, getting louder and louder as the match progressed. After both men kicked out of each other's finishers yet again, it came time for the finish. Undertaker felt some compassion for Michaels, who had nothing left in the tank, but HBK didn't want to be "disrespected" like that.

He slapped 'Taker across the face, leading to 'The Deadman' hitting arguably the most rugged Tombstone Piledriver he ever did. Three seconds later, Shawn Michaels' professional wrestling career was in the history books.