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Top 15 Most Iconic WWE Matches Of The 90s

The 1990s were probably the most revolutionary time for the wrestling industry as a whole. At one point, all of WCW, WWE and ECW were on national television, and garnering higher ratings than had ever been seen before in the business. For WWE in particular, this competition gave them the incentive to establish new, groundbreaking stars, rather than rest on their laurels. As a result, some of the best matches of the decade were seen within Vince McMahon's promotion, and are still talked about among fans to this day.

It really was no secret who the top dogs were in the company during the decade. Indeed, there are plenty of wrestlers who see multiple entries on this list, but each of their matches included here were unique, and brought something different to the table. These bouts were significant for multiple reasons; including the aspects of innovation, match quality, storyline, and so forth. Ultimately, all of the matches included here are a must-watch for any WWE fan past or present. They represented a hallmark time in the industry, and set the stage for WWEs continued dominance into the present day.

Ranked below are the top 15 iconic WWE matches of the 1990s.

29 Bret Hart Vs. Roddy Piper - WrestleMania VIII

via bleacherreport.com

This was one of the better "knock down, drag out" WrestleMania matches ever, and Hart's victory over a renowned WWE figure like Piper, was really the turning point in his career. This is really the match that put "The Hitman" on the map, and solidified him as a perennial contender, as he gained his second Intercontinental Title. The match itself wasn't one of Hart's technical masterpieces, but proved that he could do his share of brawling as well, which was when Piper was at his in-ring charismatic best. From here, Hart went on to WWE Title reigns aplenty, and was a main event staple in WWE for the next five years, before moving to WCW. This can be considered one of the most "entertaining" matches in WrestleMania history, and again, was a true stepping stone for Hart's career.

28

27 Razor Ramon Vs. The 1-2-3 Kid - Raw

via seanlcorbin.wordpress.com

When Sean Waltman made his WWE debut in 1993, as the 1-2-3 Kid, he was relegated to the role of jobber for several weeks, before scoring this upset pinfall on an episode of Raw against upper mid-card talent, Razor Ramon. While not an all-time great match, the shock factor here has made this bout a topic of conversation until the present day. Certified jobbers back then simply did not beat established stars, especially not on TV tapings of any sort. While it may seem like an afterthought today, the creativity involved in this move was actually extremely impressive for its time, and definitely was a huge stepping stone for Waltman's career. It's firmly cemented as an all-time great moment on Raw, and as such, deserves submission on here.

26

25 Randy Savage Vs. The Ultimate Warrior - WrestleMania VII

via allthebestfights.net

This retirement match in 1991 saw Savage sporting his "Macho King" gimmick, though this was the match where he reunited with Elizabeth, leaving his manager at the time, Sensational Sherri in the dust. This one will always go down as an all-time WrestleMania classic. Just the spectacle of it, two major stars at the time in a 20-plus minute bout, with the best aspects of early 1990s WWE drama and side-plots arising throughout. It doesn't quite reach the excitement level of the absolute best the decade has to offer, but it's an essential watch from 90s WWE. Most believe that this was the match that stole the show at WrestleMania VII, despite the Hogan appearing in the main event. It would be hard to disagree with that statement. One of Savage's great matches, and probably the best one the Warrior ever had.

24

23 Davey Boy Smith Vs. Bret Hart - SummerSlam '92

via cagesideseats.com

Taking at place at Wembley Stadium in Smith's home country of England, this is simply one of the most class matches in WWE history. A capacity-filled 80,000 person crowd set the stage for this Intercontinental Title match, which is probably the best bout of Smith's entire career. The atmosphere, the in-ring action, capped off by Smith's patented running powerslam to win the IC gold in his homeland; this is just an all-time WWE highlight reel moment. It's the kind of thing you see in retrospective, "through the years" video packages all the time. The stature of WWE can sometimes work against them in their worst moments, but when they do it right, it results in a refined in-ring spectacle like no other promotion can pull off. This may be the epitome of their ability to do so. This is the only time Smith would win the IC belt.

22

21 Shawn Michaels Vs. Mankind - In Your House: Mind Games '96

via listal.com

While this is just one in a long line of classic Michaels matches from the 90s, this is the one that really put Mankind, and all things Mick Foley on the map in WWE. Michaels was already established as WWE champion, but a match against Foley led him to increased respect amongs "hardcore" or "underground" fans. Foley himself had become equally established using the Cactus Jack persona in WCW and Japan, with a penchant for a defined, violent hardcore wrestling style. When the two met in a WWE ring, it assisted the careers of both wrestlers, as it also proved that Foley could hang with the main event talent in the biggest promotion in the world. The match, despite a disqualification interference ending, is still an all-time classic, with both Michaels and Foley at the peak of their in-ring careers.

20

19 Undertaker Vs. Kane - WrestleMania XIV

via sports-wallpaperz.blogspot.com

Certainly not one of the "best" matches of the decade in terms of technicality, but in terms of WWE bravado few could top this. The atmosphere was chillingly electric for this at the time, two underworld-like figures who were supposed brothers, clashing at the biggest pay-per-view of the year. In the pre-internet age, this was really something to behold. It was the first meeting between the two after months of buildup, and the match delivered with a high-impact style that really legitimized Kane in WWE. It won't win any points for technicality, but that really wasn't what was important here, and it remains one of the most entertaining matches in WrestleMania history. A confirmed classic that doesn't get nearly enough attention as it should today. Both would obviously go on to illustrious careers within WWE, and this is landmark point in their history.

18

17 Shawn Michaels Vs. Bret Hart - WrestleMania XII

via thetoplister.wordpress.com

This Ironman match for the WWE Title is always considered one of , if not the best between the Heartbreak Kid and The Hitman. The mid-card section of the roster may have been in a state of flux around this time, but main event matches like this one sure prove that WWE had that part taken care of. This is just a clinic in multiple styles of wrestling, proving that they were possibly the best two in the world at the time in any promotion. The match ended in a sudden death overtime finish, after the hour time limit had elapsed and both wrestlers were tied at the pinfall count. Michaels ended up taking the win after hitting the Sweet Chin Music on Hart. Just another high point for both of their illustrious careers, this is an all-time classic, and is a contender for the best match in WrestleMania history. Absolutely essential.

16

15 Bret Hart Vs. Owen Hart - WrestleMania X

via crazymax.org

Another match where the buildup and circumstances surrounding it made it go from "great" to "all-time classic", this was the leadoff match for the tenth WrestleMania in 1994, and saw the Hart brothers pitted against each other. Obviously, given that both Bret and Owen were highly skilled technicians, everyone knew this was going to be a clinic from the get go. It did not disappoint; the match demonstrated great psychology and timing, with both wrestlers at their peak. This level of intensity was rare for 1994-era WWE, but it was pulled off with flying colors here, as if the Hart brothers knew any other way to wrestle. Owen ended up getting the pin in a 20 minute classic. Bret would go on to face Yokozuna for the WWE title later in the pay-per-view, but this was his ultimate highlight of the night, and one could argue in his entire WWE career.

14

13 Hardy Boyz Vs. Edge & Christian - No Mercy '99

via bleacherreport.com

A tag team ladder match classic. This is the match that set up the last great era for tag team wrestling in WWE, and it did so with innovation and poise. Both teams were young at the time and itching to prove themselves on a pay-per-view level. The exuberance and athleticism was not lost on the crowd, and many knew right there that a new style of tag wrestling was set to make an appearance in WWE. It was high-risk maneuvers, combined with a distinct hardcore style that made the match so fun to watch, and it still holds up to this day. With the addition of teams a short time later, such as the Dudley Boyz, and A.P.A., it was the last time in WWE history where tag wrestling was a certified draw for the company. This bout from No Mercy spearheaded that, and is one of the most entertaining, important matches from the decade.

12

11 1992 Royal Rumble Match

via cagesideseats.com

When WWE was able to land Ric Flair in 1991 from the NWA, it was one of the biggest acquisitions for a promotion in wrestling history. Flair was the definition of a world-renowned star, and he was now able to be put in a whole new plethora of angles and matches in WWE. The winner of this Royal Rumble was set to win the vacant WWE title, and there was no better way to introduce Flair to WWEs pay-per-view audience than that. Flair was the third entrant in the match, and went the distance, in a performance that stands along with most of his all-time great matches. All in all, Flair was in the Rumble for an astounding one hour. He eliminated Sid Justice to win the title, and set himself up for a successful, yet brief first run in WWE. This is widely considered the best Royal Rumble of all time, and turned Flair into a household WWE name in the process.

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9 Shawn Michaels Vs. The Undertaker - Badd Blood '97

via pwpnation.com

This was the first ever Hell In A Cell match in WWE, and it ended up setting a benchmark for all future matches of the type. Many of the typical spots seen in future matches were used here, and they still hold up today. Fighting on top of the cell, the dive onto the announcer's table, and using the cell as a weapon in general. It was new ground for WWE at the time, and while it has become normalized today, in 1997, this was just out of this world for a mainstream wrestling promotion. Not to mention that Michaels and the Undertaker were two established main event personas that added to the drama of the match. Ultimately, thanks to the debut interference of Kane, Michaels would win the match, but not before a true classic was already cemented. One of the most violent, shocking matches of its time, this one really helped usher in the Attitude Era, and remains a staple of 90s WWE.

8

7 Shawn Michaels Vs. Razor Ramon - WrestleMania X

via knockoutnation.com

One of the most groundbreaking matches in the history of WWE, this was important in not only establishing the main event status of both Shawn Michaels and Scott Hall, but was innovative in every way back in 1994. In WWE at the time, using weapons in the actual stipulations of a match simply wasn't an accepted thing like it would later become. To have this match on a WrestleMania card, set in motion the changes that the promotion would adapt fully just a few years later in the Attitude Era. You could make the argument, that from a "wrestling" standpoint, that this was the most important match of the decade, helped in large part because it's widely considered a five-star classic match. Weapons would become commonplace in WWE later on, but at the time this was cutting edge, and was fundamental in the success of both wrestlers' career.

6

5 Hulk Hogan Vs. The Ultimate Warrior - WrestleMania VI

via cagesideseats.com

While not the best match for either wrestler, this one helped shake up the main event scene in WWE for the long term. Before this, Hogan had not lost at a WrestleMania main event before (though he did get DQ'd on a count-out against Andre The Giant two years prior on the under-card), and this was instrumental at the change that was to come. The Warrior defeated Hogan, pinning him in the middle of the ring, showing that Hogan was not the invincible champion that he had been portrayed as. Times were changing, and a new era with new main event talent was about to take over, and make their presence felt. Hogan would hold the WWE Title again, but only in a gimmicky "patriot" angle, and briefly after a run-in at WrestleMania IX. His real dominance was over, and the fans of the time were well aware of it, and looking forward to bigger and better things on the horizon.

4

3 Shawn Michaels Vs. Bret Hart - Survivor Series '97

via sportskeeda.com

The infamous "Montreal Screwjob" incident. This one match has probably been the subject of more conversation and debate than any other match of the decade. It's infamous and important on so many levels. It signaled the exit of Bret Hart from WWE (though that had already been decided before the match began), spearheaded the soon-to-be "Mr. McMahon" character, and shed unwanted light on the industry at large. The confrontations between McMahon and the Harts have gone back and forth over the years, and many people question whether this was even a shoot to begin with, estimating that it was an elaborately planned work. The background evidence of Hart leaving for WCW suggests not, and if so, it's one of the most underhanded double crosses in the history of the industry. Different in circumstance to all the other entries on here, but the debate and notoriety around this incident warrants it's place on here.

2

1 Steve Austin Vs. Bret Hart - WrestleMania 13

via m.goliath.com

Bar none, the match that had the most implications on where the WWE was headed at the time of the late 1990s. A no-DQ submission bout, with Ken Shamrock as the guest referee. This was simply just a war for the entirety of the match, and no other spearheaded Austin's popularity with the fans more than this one. After a bloody brawl that took both men outside the ring and into the crowd, Hart had his Sharpshooter finishing hold on Austin, but rather than submit despite a fully-bloodied face, Austin passed out in the center of the ring. Hart won the match, but the real benefactor was Austin, who's superstar career really took off from that moment on, and changed the entire face of the company. Other incidents and matches established Austin on the microphone, and showcased his wrestling ability, but the true "Stone Cold" toughness that connected with WWE fans was showcased here in full capacity. An all-time classic five-star match, as well as the historical significance and unique, inventive finish puts this atop the ranking for the best match of the 90s.

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Top 15 Most Iconic WWE Matches Of The 90s