At Survivor Series 1990, The Undertakermarched down to ringside alongside Brother Love and the rest is history. Undertaker went on to have one of the greatest runs in WWE that lasted 30 years. Undertaker had plenty of success as he won seven World Championships amongst other impressive accolades. He remained relevant for so long as he managed to reinvent himself and continued to find himself at the top of the card.

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Nevertheless, despite all the good times that Undertaker in WWE, there were some rough storylines that he had to endure. He was capable of being featured better, and he did his very best to get some talent over, but it didn't work. Moreover, Undertaker showed his greatness by overcoming failings from the creative team by bouncing back in style. There were some instances where WWE undermined the Demon of Death Valley.

10 Not Main Eventing WrestleMania 23

The Undertaker made history as the first man to win the Royal Rumble match from the 30th position at the 2007 Royal Rumble. The Phenom opted to remain on SmackDown, and he challenged Batista to a blockbuster World Heavyweight Championship match at WrestleMania 23.

That was a marquee match but their Raw colleagues John Cena and Shawn Michaels got the nod to close out the show. Cena and Michaels had one heck of a match, but Undertaker and Batista were positioned in the middle of WrestleMania 23. There's no doubt that they should have gone on last as they tore the house down which resulted in Undertaker winning the World Heavyweight Championship for the first time.

9 Burned At Elimination Chamber 2010

The Undertaker's legendary entrance is iconic as he traditionally takes a long stroll down to the ring. At Elimination Chamber 2010, The Undertaker was set to defend his World Heavyweight Championship in an Elimination Chamber match. However, there was a malfunction with his entrance as Undertaker was engulfed in flames.

Undertaker wasted no time in getting himself in the pod. He doused himself with water to cool off his burns, but he was visibly uncomfortable. It was a good thing that Undertaker wore his trench coat as his injuries could have been more severe. Undertaker did warn the pyro guy as he had a close call with the flames beforehand, but his words fell on deaf ears.

8 The Corporate Ministry

At the start of January 1999, The Undertaker's Ministry of Darkness stable began to take shape. The Phenom had the Acolytes, Mideon, Viscera, the Brood, and Paul Bearer by his side. Undertaker did a good job as the leader of the Ministry of Darkness as it showed a different side to him being in a faction, as he is usually on his lonesome.

However, on the pilot episode of SmackDown in April 1999, The Undertaker's Ministry fused with Shane McMahon's Corporation to become the Corporate Ministry. The issue with the Corporate Ministry was that Undertaker took a back seat with the McMahons taking a prominent role as leaders of the group.

7 Feuding With Heidenreich

In 2004, The Undertaker began a new feud with Heidenreich. Heidenreich cost Undertaker the WWE Championship twice at No Mercy and Armageddon. They finally faced off in an underwhelming match at Survivor Series with the Deadman defeating Heidenreich.

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It was clear that Heidenreich wasn't ready to be feuding with someone of the caliber of Undertaker. Their rivalry was put to bed in a Casket match at the 2005 Royal Rumble with the Phenom getting the better of Heidenreich once more. Undertaker moved on to bigger and better things as he feuded with Randy Orton for the majority of the year with Heidenreich repackaged as a babyface.

6 No Build To Match With John Cena At WrestleMania 34

At WrestleMania 34, The Undertaker and John Cena clashed which enticed fans, but it could have been even bigger if they had a proper build-up to the match. Big Match John watched some matches with fans in the crowd, and he drank some beers before he wrestled Undertaker.

It was a dream match, but it failed to live up to the hype. The bout ended up being in a squash match with Undertaker winning emphatically. Both men were part-timers at this point in their careers and there's no doubt that WWE should have booked this match sooner.

5 Facing Big Show & A-Train At WrestleMania 19

The Undertaker's legendary WrestleMania streak was mentioned at WrestleMania 17 for the first time when he beat Triple H to go 9-0. However, a couple of years later, Undertaker was scheduled to team up with Nathan Jones to collide with behemoths Big Show and A-Train at WrestleMania 19. It turned out to be a handicap match with Undertaker facing them on his own.

Undertaker deserved better, and it was a lackluster handicap match on The Grandest Stage of Them All. The Undertaker prevailed to ensure that his WrestleMania streak remained unblemished to go 11-0.

4 Six-Day WWE Championship Reign

Just one year into his WWE career, The Undertaker challenged Hulk Hogan for the WWE Championship at Survivor Series 1991. The Hulkster was rarely beaten, but with a helping hand from Ric Flair, Undertaker dethroned Hogan to win the WWE Championship for the first time in his career.

RELATED: 10 Short WWE Title Reigns That Should Have Lasted Longer

In typical Hogan fashion, he complained about the force of the Tombstone Piledriver. Hogan's head did not touch the chair with Undertaker safely executing the maneuver. However, Undertaker's WWE Championship reign was short-lived as Hogan recaptured the title just six days later on This Tuesday in Texas. Undertaker deserved to have a longer reign with the gold to prove his worth as WWE Champion.

3 Feuding With Giant Gonzalez

1993 was one of the most underwhelming years in The Undertaker's WWE career. He feuded with Harvey Wippleman's latest charge Giant Gonzalez. Their rivalry was born in the 1993 Royal Rumble match when Gonzalez made his WWE debut, and he removed Undertaker from the Royal Rumble match.

Undertaker had the worst series of matches with Giant Gonzalez, whose movement was limited as he was tall. Their matches at WrestleMania 9 and SummerSlam were atrocious, but the Deadman came out on top, and he moved into a WWE Championship title feud with Yokozuna before he took seven months off to nurse some injuries.

2 Super ShowDown Match With Goldberg

Fans were treated to a marquee match at Super ShowDown in 2019 with The Undertaker clashing with WCW legend Goldberg in Saudi Arabia. Unfortunately, the match did not go according to plan with a series of botches from Goldberg.

Both were way past their prime with Undertaker at the age of 54 and Goldberg was 52. Goldberg got concussed, and whilst Undertaker was victorious, he was far from pleased at what went down. The Demon of Death Valley was better off facing somebody else as Goldberg has never been known to be a good worker inside the squared circle.

1 Losing WrestleMania Unbeaten Streak

The Undertaker's WrestleMania unbeaten streak became as big as some marquee World Championship matches. The early stages of Undertaker's WrestleMania streak weren't good as he had some underwhelming matches against the likes of Giant Gonzalez and King Kong Bundy.

Nonetheless, the Phenom registered 21 victories at WrestleMania which is simply outstanding. However, at WrestleMania 30, Undertaker collided with an old foe in Brock Lesnar. It was a foregone conclusion by many that Undertaker would win this match. That failed to materialize with the Beast Incarnate bringing Undertaker's unbeaten record at WrestleMania to a crashing halt. Lesnar didn't need to end Undertaker's streak as he was a megastar, and adding insult to injury, Undertaker had a concussion.