10 Greatest 1990s WWE Matches

Shawn Michaels Mankind WWE Mind Games 1996

The 1990s was one of the most celebrated decades in WWE/F history. The early nineties saw the company at the tail end of its first international boom period and ended in the most lucrative run of its entire history as the promotion became a worldwide pop culture phenomenon. Events such as WrestleMania XIV and WrestleMania XV also set all-time pay-per-view buy rate records.

As a result, the decade was filled with superlative matches that are still widely revered to this day. This feature looks at the 10 greatest of the era.

#10 Bret ‘Hitman’ Hart vs Owen Hart – March 20, 1994

WrestleMania X

WrestleMania X is best remembered for two bouts; the first pay-per-view Ladder Match collision pitting Razor Ramon against Shawn Michaels and the opening match pitting the Hart brothers, Bret and Owen versus one another.

Only one contest could make the list, and it’s the superlative technical wrestling masterpiece between the Hart’s that gets the nod.

The match had been built expertly for months as Owen had been progressively becoming more envious of his elder, more famous brother before finally snapping and attacking him at the Royal Rumble. Their feud peaked at WrestleMania as the brothers put together a crisp, flawless match-up that had the Madison Square Garden crowd engrossed throughout.

One of the greatest pure wrestling matches of all time.

#9 Stone Cold Steve Austin vs Dude Love – May 31, 1998

Over The Edge 1998

Stone Cold Steve Austin claimed his first WWE Championship in the headliner of WrestleMania XIV when he defeated Shawn Michaels. Post-WrestleMania, Mick Foley was tasked with solidifying Stone Cold as the premier player in the game. Under his Dude Love persona, he wrestled two superb pay-per-view bouts with the champion.

Their second collision at Over The Edge was the best of the two. Fought under Falls Count Anywhere rules, the pair had the type of brawl that became synonymous with the Attitude Era. However, few other weapon-filled bouts could compete with this classic.

Stone Cold had the deck stacked against him as his arch nemesis, Mr. McMahon was the special referee, and stooge, Gerald Brisco was the guest timekeeper.

Filled with top-notch, stiff brawling and logical big spots, this was a match that was enhanced by the overbooking rather than harmed by it.

An Incredibly entertaining battle which became the blueprint for all Attitude Era brawls that followed.

#8 ‘Macho King’ Randy Savage vs The Ultimate Warrior – March 24, 1991

WrestleMania VII Savage vs Warrior

WrestleMania VII was headlined by Hulk Hogan versus Sergeant Slaughter but the real main event was the contest pitting ‘Macho King’ Randy Savage against The Ultimate Warrior.

Savage carried Warrior to his finest match ever in a hugely dramatic, emotional and incredibly heated bout. which had the live crowd biting for every near fall.

With both men’s careers on the line, the stakes could not have been higher. In the closing moments, Warrior nailed Savage with the big splash, but could not pin the former WWE Champion.

Doubting himself, Warrior contemplated deserting the match and accepting defeat before returning to the ring and finally finishing Savage off with three flying shoulder blocks.

The post-match was even more memorable, as ‘Sensational Queen’ Sherri beat on her charge for losing, only for Savage’s former valet (and real life wife) Miss Elizabeth to storm the ring and reunite with Savage.

The pair would marry on-screen at that year’s SummerSlam. Fabulous match and post-match with the kind of storytelling WWE excels at.

One of the best remembered matches of the era for good reason.

#7 Bret ‘Hitman’ Hart vs ‘Rowdy’ Roddy Piper – April 5, 1992

WrestleMania VIII

WrestleMania VIII played host to two classic matches; Ric Flair versus ‘Macho Man’ Randy Savage for the WWE Championship and this bout between ‘Rowdy’ Roddy Piper and Bret ‘Hitman’ Hart for IC gold.

Hart had dropped the belt on a house show to The Mountie in January, who had been dethroned by Piper at the Royal Rumble. That win marked Piper’s first ever taste of WWE gold despite his long tenure in the company.

Piper played subtle heel against the younger Hart in a match that was designed to pass the torch. The match was an expertly paced contest that featured a mix of wrestling and brawling. Hart bladed and his blood loss only added to the drama of the match-up.

The famous finish occurred when Hart reversed a sleeper into a pin to capture his second IC Title and continue his march towards the summit of the company. One of Hart’s best and unquestionably Piper’s finest match of their respective careers.

#6 Shawn Michaels vs Razor Ramon – August 27, 1995

Summerslam 1995 HBK vs Razor

Shawn Michaels and Razor Ramon contested the inaugural Ladder Match on pay-per-view on the WrestleMania X undercard. That bout was ground-breaking and is widely regarded as one of the finest matches of the era. However, the sequel at SummerSlam 1995 was even better.

With callbacks aplenty to their first encounter, bigger bumps and a more logical story, their SummerSlam match-up was an absolute scorcher.

Michaels slightly blew the finish when he failed to grab the title belt (twice) but that just made the finish even more dramatic.

‘The Heartbreak Kid’ (eventually) pulled down the Intercontinental Title to retain the gold and avenge his WrestleMania defeat.

#5 Stone Cold Steve Austin vs Bret ‘Hitman’ Hart – November 17, 1996

Survivor Series 1996

Stone Cold Steve Austin and Bret ‘Hitman’ Hart were always magic together in the ring. Their first high profile match-up took place at the 1996 Survivor Series. Occurring before Austin’s knee and neck injuries drastically altered his wrestling style, this bout saw both men compete in a technical wrestling classic.

The pair tortured each other for close to 30 minutes with a mix of wrestling, excellent counter wrestling and some devastating big moves in a logically paced and realised encounter.

This marked Hart’s return after taking an eight month sabbatical from the Federation after WrestleMania XII and demonstrated he had not missed a beat in his absence. For Austin, his performance showed he belonged at the top of the card.

In an interesting callback to WrestleMania VIII, Austin fell victim to the same sleeper/pinfall reversal Hart had also successfully performed on Piper four years earlier.

The pair would contest a far more famous bout at WrestleMania 13 four months later, but this match-up is a stunningly good first chapter in their classic feud. Unquestionably one of the best matches of the decade.

#4 Shawn Michaels vs Mankind – September 22, 1997

Mind Games Michaels vs Mankind

Shawn Michaels’s first WWE Title reign featured some all time classic matches. The best of the bunch was his bout with Mankind at Mind Games: In Your House in September 1996.

Although the match ended in a disqualification, no one remembers that fact. That’s because the preceding 26 minutes were filled with fast-paced, non-stop action.

In a departure for the company at the time, the contest featured more violent spots than was typically associated with the family-friendly promotion. The highlight of which was Mankind being dropped onto the concrete floor, with the protective mat removed, directly onto his back.

The bout was an excellent brawl which was the precursor to the style that would become vogue in the WWE during the Attitude Era. The contest legitimised Michaels as a tough guy as well as a finesse wrestler. Mankind’s alter ego, Cactus Jack would perform the same role for Michaels’s buddy, Triple H four years later at the 2000 Royal Rumble.

A special match. Unquestionably the match of the year in 1996.

#3 Bret ‘Hitman’ Hart vs Mr. Perfect – August 26, 1991

SummerSlam Hart vs Perfect

SummerSlam 1991 was significant for being the show in which The Ultimate Warrior was fired, the final pay-per-view appearance of Andre The Giant and the debut on pay-per-view of Sid Justice.

However, its greatest significance was on the undercard, as tag team wrestler, Bret ‘Hitman’ Hart proved he could be a legitimate singles star in a barn burning battle with Mr. Perfect.

Hart had significant fan support and proved he could hang with one of the company’s finest workers in a topsy turvy, technical masterpiece that lasted an epic (for the time) 29 minutes.

Crammed full of crisp moves and fluid counter-moves, this match was a sensational contest.

Hart forced Perfect to submit to the Sharpshooter to lift his first singles title in the WWE, the Intercontinental strap.

The win established ‘The Hitman’ as a major player and just 14 months later, he would win the WWE Championship from Ric Flair.

#2 Shawn Michaels vs The Undertaker – October 5, 1997

Badd Blood

In October 1997, the WWE presented its first ever Hell in a Cell contest. Differing from the traditional Cage Match by utilising a wire mesh fence and enclosing the structure with a roof, the cell was an imposing structure.

It was created to contain the wildly out of control feud between D-Generation X’s Shawn Michaels and The Undertaker. After a singles contest between the pair had been thrown out due to copious amounts of outside interference, the steel structure locked the pair inside the demonic confines of the cell.

‘The Phenom’ battered his foe senseless in the early going before Michaels managed sporadic comebacks. After failing to keep the ‘Deadman’ down, Michaels beat up a ringside cameraman to enforce the opening of the cell door.

An opportunistic ‘Showstopper’ then escaped the cage and climbed onto the roof. Unfortunately for him, The Undertaker was in hot pursuit and sent Michaels flying off the side of the cage through the announcer’s table.

With Michaels beat, The Undertaker appeared set to win the bout. However, a debuting Kane smashed his brother with a Tombstone and a semi-conscious, ‘HBK’ covered the ‘Deadman’ to win.

Bloody, violent and engaging with pitch perfect storytelling, the inaugural Hell in a Cell contest is close to perfect.

#1 Stone Cold Steve Austin vs Bret ‘Hitman’ Hart – March 23, 1997

WrestleMania 13

Bret ‘Hitman’ Hart and Stone Cold Steve Austin were not originally scheduled to battle each other at WrestleMania 13. Prior plans had seen Stone Cold set to clash with The British Bulldog and Hart was supposed to clash with Shawn Michaels in a rematch of the previous year’s WrestleMania. However, as Michaels was set to return the favour and lose to Hart, ‘HBK’ sidestepped the job by exaggerating a knee injury.

Thankfully, Stone Cold versus Hart was so good, no-one was disappointed by the change to booking plans. In an expertly laid out contest, Stone Cold and Hart battered each other senseless, with high impact moves and weapons such as chairs and the ring bell.

The finish came when Stone Cold after being smashed in the face with the ring bell eventually passed out in ‘The Hitman’s’ patented Sharpshooter submission hold.

The image of blood pouring down ‘The Rattlesnake’s’ face as he writhed in agony was immortalised in the opening to Monday Night Raw for over a year. 25 years later, and that image still retains its power.

Fans turned on Hart after he battered an unconscious Austin post-match and he had to be restrained by the special referee, former Ultimate Fighter, Ken Shamrock.

Hart left the ring a hated heel and Austin, a superstar babyface and the biggest star in the business. Many trace the start of the Attitude Era to this match, given it was bloodier and more violent than anything the company had produced for well over a decade. Its influence set the tone for the Federation’s immediate future and helped propel WWE to its greatest creative and financial period ever.

This bout was a masterpiece and is unquestionably the greatest match of the 1990s.

You can watch all of these legendary 1990s bouts exclusively on the WWE Network.