WWE news: Ranking The Undertaker’s 27 WrestleMania matches from worst to best (27-11)

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The Undertaker is one of the most popular and successful wrestlers in WWE history.

After making his debut in 1990, the wrestler helped to transform the popularity of the sport by becoming one of its flagship stars.

He is mainly associated with WWE’s main annual event WrestleMania after winning a streak of 21 victories. The Undertaker even headlined the event on five occasions, a feat only beaten by the likes of Hulk Hogan and Triple H.

Because of his enduring legacy and success at the event, What Culture have ranked The Undertaker’s 27 WrestleMania from worst to best.

Here we go.

27. WrestleMania 33 vs Roman Reigns

While The Undertaker’s entrance at WrestleMania 33 was a legendary spectacle, the fight against Roman Reigns was not. Reigns was tipped as the next generation’s top dog in WWE, but his victory over the star was slow and tiresome to watch.

It was made worse by the fact that ‘The Deadman’ was out of shape and suffering from a hip injury at the time, which just slowed down the fight even more.

26. WrestleMania IX vs Giant Gonzalez

This fight was billed as one of the best in WWE history, but was let down by the Giant’s weird bodysuit and cartoon abs. The bout felt gimmicky and was slow, partly as a result of Gonzalez’s actions rather than The Undertaker’s.

25. WrestleMania XIX vs Big Show and A-Train

This fight was underwhelming to say the least, with the only real important part being Biker ‘Taker’s Tombstone, which is a fan favourite at the event.

24. WrestleMania XI vs King Kong Brody

WrestleMania XI, which took place a year after The Undertaker’s rebirth, saw a six-minute smackdown which felt a lot longer than it actually was. Slow-moving action helped to make this one of the most uninspiring matches of his legendary career.

23. WrestleMania XXX vs Brock Lesnar

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Brock Lesnar’s streak-ending win is one of the most famous moments in history, but the fight certainly wasn’t one of the best.

The Undertaker suffered a concussion early on, making the rest of his appearance almost like a deer in headlights in the face of Lesnar’s performance.

22. WrestleMania XV vs Big Bossman

WrestleMania XV is much more memorable for what happened after the actual fight, which shows how it was pretty uninteresting at the time. The fighters even had a Hell In A Cell at their disposal, but failed to use it convincingly.

This fight will be one of the more easily forgotten ones in The Undertaker’s long career.

21. WrestleMania VII vs Jimmy ‘Superfly’ Sunka

This was ‘Taker’s first appearance at WrestleMania, long before his winning streak was even an idea. Although the match wasn’t one of the best, it will certainly be remembered as a form of passing the torch to the next breed of wrestlers.

The Undertaker ended the bout with one of the best Tombstones of his career.

20. WrestleMania 34 vs John Cena

Fellow WWE legend John Cena faced ‘Taker at WrestleMania 34 back in 2018, with Cena being put away inside three minutes. The Undertaker wasn’t in his best form, but after a major hip operation, it made sense to slowly ease himself back into the sport.

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19. WrestleMania 13 vs Sycho Sid

In front of over 18,000 fans, The Undertaker faced Sycho Sid in 1997. The match took place during his evolution which saw him bring new moves to the ring, but the fighters’ lack of ring chemistry ultimately meant it was a flawed bout in more ways than one.

18. WrestleMania VIII vs Jake Roberts

‘Taker faced his former partner Jake Roberts at WrestleMania VIII, in a fight which continued the legend’s upward trajectory towards success. There wasn’t much action to complain about, but then again, there wasn’t too much action at all.

17. WrestleMania XX vs Kane

WrestleMania XX saw Kane and ‘Taker’s rematch after their stunning first bout. The image of the returning Undertaker walking through Madison Square Gardens while druids held flaming torches over his head will be remembered for years by WWE fans, although the bout itself did not quite live up to this hype.

16. WrestleMania 32 vs Shane McMahon

The length of this one was the main reason why it didn’t go down in history as one of the greats. The Undertaker defeated McMahon in Texas in a Hell In a Cell match. One incredible spot from Shane-o-Mac wasn't enough to put it any higher in the list.

15. WrestleMania 32 vs Mark Henry

His casket match against Mark Henry at WrestleMania 32 saw The Undertaker get back to his very best, including a stunning Last Ride, his first Suicide Dive in years and, of course, his signature Tombstone.

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These all helped WrestleMania 32’s ending to surpass what was overall a very average fight.

14. WrestleMania 31 vs Bray Wyatt

WrestleMania 31 followed on from Brock Lesnar’s victory over ‘The Deadman’, which to many signalled the end of his career. However, he proved many fans wrong and managed to return to the ring with a strong display against Bray Wyatt, one which brought back memories of the sport’s glory years.

13. WrestleMania XII vs Diesel

His match vs Diesel in early 1996 saw a fight that was more interesting than the typical ‘monster vs monster’ bout. However, it wasn't strong enough to break the top 10.

12. WrestleMania 36 vs AJ Styles

‘The Deadman’ fought AJ Styles earlier this year in what was one of the more intriguing fights in WWE history. The bout was shot as a mini horror film and was largely based on horror theatrics, which worked well alongside The Undertaker’s undead persona.

The lack of fans made this a very different affair to ‘Taker’s typically huge stadium appearances, but the horror elements worked well to give WrestleMania a new feel.

11. WrestleMania XIV vs Kane

Kane and ‘Taker’s feud has gone down as one of WWE’s best pieces of storytelling, mainly down to the revelation that Kane is actually his long lost brother.

This fight was an absolute war between two great fighters at their very best. It took ‘The Deadman’ three Tombstones to finish off his opponent, after previously being knocked around the ring for most of the fight.

You can see 10-1 of The Undertaker's best WrestleMania matches here.

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