The 10 Most Important WWE Matches Of The 1990s

The 1990s were a decade of change for all of wrestling. As it began, WWE and WCW were dominating but there were still scores of smaller territories. By the end of the decade, WWE was dominant with WCW and ECW on their last breaths. The changes were also abounding on other ways. The decade began with ridiculous cartoonish characters and ended with serious “Attitude.” New stars were made while older ones slowly faded but some stuck around. The entire landscape changed in ways no one could possibly have predicted in 1990.

Numerous moments are pointed to as key to WWE’s success. Most of them came in the Monday Night War but even beforehand there were incidents that paved the way for the company’s dominance. Many matches were forgettable but some truly stood out from the pack. Listing the greatest matches of the ‘90s is easy but finding the ones truly critical to WWE is tougher. Here are the 10 most important WWE matches of the 1990s and how each was key to the company taking over by 2000.

Related: The 10 Greatest Wrestlers From the 1990s

10 Bret Hart vs Ric Flair, October 12th, 1992

As 1992 went on, fans expected the obvious moment of the Ultimate Warrior beating Ric Flair for the WWE title. Instead, out of nowhere, Bret Hart upset Flair at a Canadian house show to win the belt. In retrospect, it was a massive shift from the over-the-top musclemen like Warrior and Hogan to a smaller technical guy like Bret.

His first reign was good and would pave the way for other “smaller” stars to also break out big. Not only was it historic for Bret but WWE itself for the dawn of a new era.

9 Hulk Hogan vs Ultimate Warrior, Wrestlemania VI

It was supposed to be important for a different reason. When Hulk Hogan and the Ultimate Warrior faced off at Wrestlemania, it was not just two babyfaces going at it but the two biggest stars, title vs title. Most thought Hogan would end up victorious but instead, the Warrior pulled off the stunning upset.

It was supposed to be the Warrior then made the face of WWE and leading the company into the decade. Instead, it would become clear fans just couldn’t let go of Hogan and the Warrior faltered. Not just an epic Mania main event but a showcase for how Hogan was a vital part of WWE’s history.

8 Steve Austin vs Owen Hart, SummerSlam 97

One botched move was all it took to change so much for WWE. The plan was for Steve Austin to take a few piledrivers from Owen Hart but then pin him for the IC title. That would push Austin and lead to a showdown with Bret for the WWE title. But somehow the usually perfect Owen Hart did the move wrong, breaking Austin's neck. Somehow, Austin got the strength to roll Owen up for the title but clearly hurt.

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This would put Austin on the shelf but his attacks on others just made him hotter than ever. It also meant that instead of Bret vs Austin, it became Bret vs Shawn to set up Montreal. There was also how it would change Austin from a technical worker to a brawler and thus this botched move shifted so much of the Monday Night War.

7 The Undertaker vs Mankind, King of the Ring 1998

While Mick Foley had his fans, he just wasn’t seen as a huge deal to many fans and not a consistent main event star. He and Undertaker weren’t expected to have much to do in a Hell in the Cell match. Instead, they put on an absolute brutal classic with Foley shocking everyone by taking a massive bump off the top of the Cell and then right through the roof.

Related: 10 Ways WWE Has Become Just Like WCW

It was an incredible display of guts that instantly made Foley a legend. It laid the seeds for his eventual championship win and his best-selling book that both helped push WWE up majorly.

6 Steve Austin vs Jake Roberts, King of the Ring 1996

It’s not so much the match but its aftermath. Steve Austin had busted his lip in an early KOTR match and had to get stitches.

He then heard Jake Roberts using some Bible quotes in a promo. After beating Roberts to win the tournament, Austin ignored the usual cape and crown. Instead, he bad-mouthed Roberts and then uttered the promo that would change not just his career but WWE itself: “Talk about your psalms, talk about John 3:16. Austin 3:16 says I just whupped your ass!” It made Austin the huge star of a new time and a turning point for WWE itself.

5 Mankind vs the Rock, December 28th, 1998

The circumstances is what elevated this so much. The match was filmed in late 1998 as Mankind tricked Vince McMahon into giving him a no-DQ match with the Rock for the WWE title. It was a wild brawl marked by Steve Austin coming out to an insane pop to hit the Rock with a chair and let Mankind win.

Related: 5 Wrestlers Mick Foley Loved (& 5 He Strongly Disliked) 

The fans went wild at veteran Mick Foley finally getting to the top. What really made it important was when WCW foolishly gave away the win on “Nitro”, causing scores of viewers to flip the channel. That, combined with the Fingerpoke of Doom, ended up being the key turning point of the Monday Night War.

4 Shawn Michaels vs Razor Ramon, Wrestlemania X

If ever a match was a game-changer, this was it. Ladder matches weren't a thing on a national level in 1994, but Razor Ramon and Shawn Michaels changed that pretty quick.

The two took bumps and hits never seen before and had the MSG crowd infatuated. The thrills were amazing before Ramon finally scaled the ladder for the belts. It paved the way for every ladder match since while elevating both men majorly and still one of the best Mania matches of all time.

3 Bret Hart vs Steve Austin, WrestleMania 13

It’s probably the greatest double turn in wrestling history. At Wrestlemania 13, Bret Hart was to face Steve Austin in an “I Quit” match which fans thought would be a good battle. They never expected a full-on brutal, bloody classic with each man going wild in it. It all culminated in Austin in the Sharpshooter, his face a crimson mask but refusing to give in.

Related: 5 Wrestlers Bret Hart Loved (& 5 He Strongly Disliked)

By this point, the Chicago crowd were firmly on Austin’s side and cheering him on. When Bret attacked Austin after the bell, the crowd booed him hard. In one match, Bret was the heel and Austin the mega-hero fans loved which paved the way for the Attitude Era.

2 Shawn Michaels vs Kevin Nash, May 19th, 1996

It’s not so much the match itself that’s important but the aftermath. It was well known by fans this was Kevin Nash and Scott Hall’s last night with WWE before leaving. After Shawn beat Nash, out came Hall, Waltman and Hunter as the “Kliq” hugged in the ring and bid the fans good-bye.

Back in 1996, seeing faces and heels doing this was outrageous. Someone had to take the fall and with Hall and Nash gone, Waltman soon to follow and Shawn champ, that left Hunter. His planned KOTR win was instead given to Steve Austin which changed the entire course of WWE. That alone makes this an epic event for the decade.

Related: 5 Wrestlers Shawn Michaels Loved (& 5 He Strongly Disliked)

1 Bret Hart vs Shawn Michaels, 1997 Survivor Series

To this day, the arguments rage on who was right and who was wrong. Yes, Vince doing this to Bret Hart was bad but Bret can also be seen as far too stubborn. He had to know going to WCW as WWE champion would be a bad move yet Bret acted like losing to Shawn Michaels in Canada would be a national tragedy.

It all set up a wild match that concluded with the most infamous moment in wrestling history: As Shawn had Bret in the Sharpshooter, Vince ordered the bell rung and Shawn made the champion. The fallout would transform everything as this was actually a key turn in the War that created “Mr. McMahon” and laid the seeds for WWE’s domination of the business.

Next: 5 Awesome Attitude Era Moments (& 5 That Don't Hold Up)

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