The Undertaker vs. Sting and WrestleMania Dream Matches That Should've Happened

Mike Chiari@mikechiariFeatured ColumnistMarch 17, 2018

The Undertaker vs. Sting and WrestleMania Dream Matches That Should've Happened

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    Phelan M. Ebenhack/Associated Press

    WrestleMania is often the place where dream matches become reality, but several such bouts have slipped through the cracks over the years.

    Whether by choice or bad luck, WWE has missed out on some big-match opportunities over the course of WrestleMania history. While the Showcase of the Immortals has developed into the greatest spectacular in sports entertainment, it could potentially be even bigger now had certain contests taken place.

    The Undertaker versus Sting is undoubtedly the biggest dream match that WWE dropped the ball with, but it is far from the only one since WrestleMania's inception in 1985.

    As WrestleMania approaches its 34th edition, here is a look at some of the biggest dream matches that never occurred on the Grandest Stage of Them All.

The Undertaker vs. Sting

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    Don Feria/Associated Press

    Throughout the 1990s, The Undertaker and Sting were two of the biggest and most popular stars in their respective companies.

    Along with Ric Flair, Sting was the face of WCW, while The Undertaker shared the spotlight in WWE with legendary Superstars such as "Stone Cold" Steve Austin, The Rock, Shawn Michaels and Bret Hart.

    Sting and Taker initially appeared to be contrasting characters, as Sting wore bright colors and portrayed a surfer gimmick, while The Deadman wore all black and represented the macabre.

    That changed when Sting underwent a complete character transformation. He ditched the neon gear for a black singlet, leather jacket and bat, while painting his face black and white as well.

    Sting spent the better part of the year lurking in the rafters as the nWo's biggest rival, and his popularity reached an all-time high at that point.

    Once WWE bought WCW in 2001, fans eagerly awaited Sting to sign with the company and feud with The Undertaker.

    It seemed to be a natural fit due to their dark and mysterious gimmicks, but the Stinger was reluctant to join the company he competed against for so many years.

    Instead, Sting eventually signed with TNA and remained with the promotion through 2014. Although he was well past the age of 50, Sting finally decided to sign with WWE in pursuit of a WrestleMania moment.

    Rather than immediately booking The Undertaker against Sting at WrestleMania 31, WWE took a huge risk by having Sting take on Triple H.

    Sting lost that match, but he went on to have a couple of additional matches, including a WWE World Heavyweight Championship bout with Seth Rollins at Night of Champions 2015.

    Unfortunately, Sting suffered a neck injury in that match, and he hasn't competed since.

    WWE had everything it needed to finally make The Undertaker versus Sting a reality, but it instead put the bout off, which cost it what would have been one of the most highly anticipated contests in pro wrestling history.

Daniel Bryan vs. Brock Lesnar

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    Don Feria/Associated Press

    The David versus Goliath story is perhaps the easiest one to tell in wrestling, and there is no better example of it than Daniel Bryan playing role of David and Brock Lesnar representing Goliath.

    Bryan is the ultimate underdog who few expected to ever reach the heights he was able to ascend to in WWE. He is a smallish wrestler who excelled on the independent scene, but he never fit the mold of what WWE typically looked for in a top star.

    By contrast, Lesnar was pushed to the moon immediately upon arriving in WWE, and as a collegiate wrestling champion, it was clear that he had the type of pedigree WWE looks for.

    Despite the adversity working against him, Bryan managed to find his way to the top of the company. An organic groundswell of support pushed Bryan into an enviable position at WrestleMania XXX.

    Bryan beat Triple H in the opening match of that show to qualify for the main event against Randy Orton and Batista for the WWE World Heavyweight Championship. The leader of the Yes Movement won that match as well, which led to one of the biggest celebrations in WrestleMania history.

    An injury kept Bryan out for much of the next year, but he was able to return in time for the Royal Rumble, and it was clear that the entire crowd wanted Bryan to win that match.

    WWE went with Roman Reigns instead, but it gave Bryan a chance to become No. 1 contender when he faced Reigns for that right at Fastlane 2015.

    The winner would go on to face Lesnar for the title at WrestleMania 31, and although Bryan pushed Reigns to the limit, The Big Dog managed to prevail.

    Instead of facing Lesnar, Bryan opened the show by winning the Intercontinental Championship in a ladder match.

    Bryan got injured again shortly thereafter, which ended any and all hope of a clash with Lesnar. The story in that match likely would have been remembered for years to come, but fans are instead left to wonder what could have been.

Hulk Hogan vs. Ric Flair

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    Evan Agostini/Associated Press

    Hulk Hogan helped launch professional wrestling into mainstream popularity in the 1980s, and he is among the biggest reasons why WrestleMania became such a massive success.

    Meanwhile, Ric Flair carried the flag for WCW/Jim Crockett Promotions and was undoubtedly the biggest star in the southern part of the United States.

    Hogan was a real-life superhero who told his Hulkamaniacs to take their vitamins and say their prayers, while Flair was a cocky high-roller who had no problem taking shortcuts if it meant escaping with the title in tow.

    They were seemingly made to feud with one another, but it was difficult to envision either man jumping ship to the competition.

    It finally happened in 1991, however, when the Nature Boy made the leap to WWF and proclaimed himself the real world champion.

    After controversy involving Hogan, Flair and The Undertaker caused the WWF Championship to be vacated, Flair won the 1992 Royal Rumble to become WWF champion for the first time.

    Hogan and Flair worked against each other on the house show loop on numerous occasions leading up to that, and every indication was that they would do battle in the main event of WrestleMania VIII.

    Instead, Flair branched off into a feud with Randy "Macho Man" Savage, while Hogan took on former friend Sid Justice in the main event.

    Flair versus Savage had a great story involving Elizabeth, and the match itself was solid, but it didn't have the same drawing power that Hogan and Flair would have.

    Since Hogan and Flair were still in their wrestling prime at that time, they could have put on a spectacular match that would have been replayed for decades to come.

    Hogan and Flair did go on to face each other in WCW when Hogan shockingly signed with the company, but the magnitude just wasn't on par with WrestleMania.

The Rock vs. Shawn Michaels

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    Chris Pizzello/Associated Press

    The Rock and Shawn Michaels are two of the most electric entertainers in the history of the business, which would have made them a natural fit to lock horns at WrestleMania.

    That never happened. In fact, The Rock and HBK never had a match of any kind against each other at any event, which was a significant missed opportunity on WWE's part.

    The Rock and Michaels never crossing paths at WrestleMania was as much due to bad timing as it was the decisions WWE made.

    HBK missed several years due to a back injury during The Rock's ascent, and had Michaels been active during that time, it is safe to assume that there would have been a program against the People's Champion, perhaps culminating at WrestleMania.

    Michaels came back for WrestleMania XIX to face Chris Jericho, while The Rock took on "Stone Cold" Steve Austin at that show in what turned out to be the Texas Rattlesnake's final match.

    Due to the importance of that bout with Austin retiring and The Rock finally beating him after three tries, it was a match that needed to happen.

    The best chance of Michaels against The Rock at the Showcase of the Immortals was WrestleMania XX. The Rock teamed up with Mick Foley to face Evolution at that event, while HBK competed in a Triple Threat match for the World Heavyweight Championship with Triple H and Chris Benoit.

    Although the Triple Threat was a fantastic match, a singles bout between Triple H and Benoit would have been great as well.

    The Rock 'n' Sock Connection against Evolution match was essentially a throwaway, and it wouldn't have been missed had WWE shifted The Rock into a program with Michaels instead.

    Since The Rock didn't compete at another WrestleMania after WrestleMania XX until WrestleMania XXVIII, and Michaels retired after WrestleMania XXVI, there wouldn't have been another chance to make the match happen.

    The Rock and Michaels undoubtedly would have torn the house down, and a match between them likely would have caused WrestleMania to be looked back upon in a more positive light.