When wrestlers reach the pinnacle of their careers, fans begin to postulate about what their best match could possibly be. Pitting larger than life superstars in the ring in dream matches is a big pastime for wrestling fans. Some big ones finally happened and exceeded expectations - like John Cena and AJ Styles - or never got to occur due to poor timing - like The Undertaker and Sting.

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However, sometimes these big dream matches finally occur when the stars align. Some of these matches have been built up for so long that it would be hard to meet the expectations, which is exactly what happened to some of these encounters. While it would be great if every match was what fans wanted it to be, it unfortunately occurs more often than not that they disappoint fans.

10 WWF Vs WCW

When the fight between the two brands which started the Monday Night War finally became a reality, fans were fully engaged on the opportunity to see multiple dream matches between WWE and WCW superstars. Unfortunately, when some of the biggest WCW stars (like Goldberg and Hulk Hogan) did not have their contacts picked up by WWE, fans were treated to feuds with some less-than-top talent. Besides wrestlers like Booker T and DDP, it was truly the lower tier WCW talent who showed up to "invade", leaving fans wanting much more.

9 Shinsuke Nakamura Vs AJ Styles

Following multiple matches in New Japan Pro Wrestling, the big name match between AJ Styles and Shinsuke Nakamura would finally take place in a WWE ring. Instead of burning down the ring with their athletic prowess, fans were left very underwhelmed with this showdown, and it was labeled a failure by the wrestling community.

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Styles himself commented on the letdown of the match, saying that "Expectations are way too high. I know Nakamura (thought so) too because no matter what we would have done in that match, the expectations were way too high. "

8 Ric Flair Vs Hulk Hogan

At the top of their respective games, there is no denying that both Ric Flair and Hulk Hogan were among the best in the professional wrestling business. Flair was known as one of the best in-ring performers from the NWA/WCW and Hogan was the charismatic crown jewel of the WWE, so naturally fans could not wait until they would eventually clash. However, very few fans actually got to see the letdown of a match, which took place on a WWE house show in 1991. Rumor has it that Vince viewed the match as poorly executed, which prompted a change in the card for WrestleMania XIII.

7 The Undertaker vs Goldberg

WWE's Saudi Arabia events have been highly criticized for their use of aging performers, and this match showed exactly why.

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This match at Super Showdown 2019 between The Undertaker and Goldberg was clumsy and featured one of the worst performances in recent memory. In fact, The Undertaker himself considers it one of his worst matches on record, and called it both "disappointing" and "catastrophic".

6 Shawn Michaels Vs Mr. Perfect

When fans think about some of the best in-ring technicians to step into a WWE ring, both Shawn Michaels and Mr. Perfect are usually among the top of this list. Unfortunately, when they finally locked horns at SummerSlam 1993 for the Intercontinental Championship, fans were left very confused why they looked like they were out of gas so quickly. Combining Michaels' inexperience in big match situations at the time with Hennig's back injury, and it made for a very lackluster encounter.

5 Sting Vs Triple H

By the time WrestleMania 31 rolled around, there were very few "once in a lifetime" matches left for WWE to market. However, when Sting finally came to a deal with WWE, options opened up and he was booked with Triple H for his first match with the company. Instead of a big-time match, fans were instead treated to an over-booked spectacle featuring appearances by the nWo and DX, which was not what fans had signed up for.

4 Bret Hart Vs Vince McMahon

When real-life blows onto televised feuds, it has the potential to make for some of the best wrestling matches due to the real-life feelings involved.

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There was no bigger blood feud than between Vince McMahon and Bret Hart following the Montreal Screwjob, yet the only locked horns when they were both much older. Combine their age with Hart's sustained injuries, and they were not able to compete on the level which fans had hoped. Their showdown at WrestleMania XXVI was one big letdown.

3 Hulk Hogan Vs Shawn Michaels

Shawn Michaels and Hulk Hogan faced each other at SummerSlam 2005 in a billed Icon vs Icon match. Considering that this match had never happened before, fans were actually very excited for it. However, backstage politics prevented this feud from going far, and instead of a planned three-match feud, fans instead got one match with Hogan winning, but not without Michaels acting out throughout the match to try and embarrass Hogan.

2 John Cena Vs The Undertaker

John Cena and The Undertaker did lock horns during the beginning of Cena's career on SmackDown, yet this was the first time they clashed following Cena's stint on top of the company. By the time WrestleMania 34 rolled around, both wrestlers were part-time performers, but fans were still excited at the prospect of them wrestling. However, when the match only lasted two minutes and 47 seconds, they were understandably left disappointed.

1 The Rock Vs CM Punk

Both men are widely considered to be two of the best talkers in WWE history, but were unfortunately competing in two different generations. So when The Rock returned to WWE in 2012 and feuded with the reigning WWE Champion, fans were excited about the potential match and lead-up promos that they would get. Both matches were underwhelming and so  were the promo. Punk and The Rock's showdowns at the 2013 Royal Rumble and Elimination Chamber pay-per-views did not meet expectations. Perhaps it was due to Punk being frustrated or with The Rock being past his prime, but it was not what everyone had hoped it would be.

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