Somewhere between Hulkamania running wild through the early years of Wrestlemania and Stone Cold Steve Austin leading the Attitude Era to unseen heights,WWE’sNew Generationsits in something of a pro wrestling limbo. Sneered at from outside sources and even disparaged by the company themselves when recounting the history of the Monday Night Wars, it’s important to remember that it wasn’t all The Goon and King Mable. Some ofthe greatest wrestlers of the 90s put on underappreciated classics throughout this era, matches that defy the much-maligned era’s stained reputation.
As you would expect,this list is dominated by Bret Hart and Shawn Michaels,but that is bound to happen when you have two of the greatest in-ring performers of all time, both putting on classics with everyone they worked with, while working in their prime. What is a little more surprising is some of the all-star matches that happened and overlooked contests that add a vital layer of context to 90s wrestling’s overall narrative.
10Bret Hart vs The British Bulldog
In Your House 5, December 17th,1995
Always in the conversation forbest SummerSlam Main Event of all timeand best Intercontinental Championship match too, Bret Hart vs ‘The British Bulldog’ Davey Boy Smith at Wembley Stadium in 1992 has earned its historic place in wrestling folklore. What is lesser known is thatthese two had another absolute banger at the end of 1995 for the WWE Championshipat In Your House 5: Season’s Beatings. It is a stunning match that some consider to be technically better than their SummerSlam classic.
The British Bulldog was working heel at the time, aided by Jim Cornette. As Hart has revealed in recent years, Davey Boy was highly inebriated for their 1992 match, butBulldog and Hart have a much more energetic and intense exchange here. Hart is busted open by a corner shot from Bulldog but is able to win with an incredible technical roll-up pinfall. This may not have the prestige of Wembley Stadium but this war from Hershey, PA is vital viewing.
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9Steve Austin vs Vader
Monday Night Raw, December 16th, 1996
1996 was a huge year in the career of Steve Austin. It was the year he made his debut as The Ringmaster, he then found his way to the Stone Cold character that would define his legacy, and he won King Of The Ring in June. As the year came to an end, and four months short of his breakout performance at WrestleMania, Steve Austin and Bret Hart would begin a Hall Of Fame-worthy feud for the ages. With the Royal Rumble approaching and a host of potential contenders for The Hitman’s WWE Championship,Steve Austin went to war with Vader to prove his worthiness to Bret Hart, who is sitting in on commentary.
As you would expect from two of the 90s toughest wrestlers, Vader vs. Stone Cold is a roughhouse masterpiece from the vault. It’s not a PPV and there aren’t enormous stakes, but this is a generational match that feels straight out of a video game. The fighting on the outside and in the ring is as much a brawl as it is a contest, all as Bret Hart gets more agitated as the match goes along.
The finish of the match is an absolute free-for-all allas Bret Hart ends the match by putting Austin in the Sharpshooter on the outside. Furious at being cost the match by DQ, Vader and Hart go at each other before officials intervene. A fascinating look at how Hart and Austin began to make magic via one of the best monsters of all time.
8Shawn Michaels vs Razor Ramon
Monday Night Raw, August 1st, 1994
It is incredible that people pour scorn on this entire era when matches like this exist on a random episode of Monday Night Raw.Coming sandwiched between their legendary ladder matches at WrestleMania 10 and SummerSlam 1995, this is an exciting clinic that shows that these two did not need any stipulation to make magic in the ring together. The match isn’t for a title either. It’s just about beef and a battle for supremacy.
The match came just a few months after Diesel had taken Razor’s Intercontinental Championship, with Michaels and his buddy bringing further pain to Razor in this match. After a back-and-forth match fueled by an intense sense of desperation, the referee missed Diesel’s big boot, enabling Michaels to win with a sneaky roll-up. The post-match beatdown and cowardly victory isa great example of the relationship between Michaels and Kevin Nashbefore he set off for WCW.
7Owen Hart vs Shawn Michaels
In Your House 6, July 31, 2025
Everyone knows of the iconic WrestleMania Iron Man Match between Shawn Michaels and Bret Hart. What is all too often overlooked is the match that paved the way for that classic to happen. Coming just two months ahead of the Showcase of the Immortals,the Number One Contender’s Match between Shawn Michaels and Owen Hart to face Bret Hart at WrestleMania12for the WWE Championship is a massive part of that story.
Shawn Michaels is at his heartthrob babyface best here, working the crowd as much as he is his opponent. Owen Hart’s technical and hard-hitting style was the perfect foil for him at that moment. There’s a lot of mat-based wrestling, and it may be on the weaker end of grandstand superkick finales, butShawn Michaels’s victory here set up one of the most legendary moments in WrestleMania history.
6Steve Austin vs Savio Vega
King Of The Ring Quarter Final, Monday Night Raw, July 07, 2025
90s Puerto Rican superstar Savio Vega was Steve Austin’s only WrestleMania match while still in the Ring Master gimmick. Fast-forward to July of that same year, Steve Austin was finding his feet with his new Stone Cold character, and on the road to the 1996 King Of The Ring, where he would deliver his famous 3:16 promo. Savio Vega and Austin would meet in the quarter-final stage of the tournament ina match that altered the wrestling landscape forever.
After a barbaric match that was largely focused on pain and dropping bombs on one another,Stone Cold won this match by using The Stunner for the first time. The move didn’t have the knee to the gut pre-cursor to the move and it didn’t have the devastating visual effect that would come to define the move, but this is the first time that Steve would win with his signature finishing maneuver. The rest is history.
5Bret Hart & Owen Hart vs The Steiners
Wrestling Challenge, January 11th, 1994
It is a match that feels as though it was lost to the sliding doors of time, but on the road to the Royal Rumble 1994,these two teams of brothers met for the only time on a random episode of Wrestling Challenge. Owen Hart and Bret Hart were on their way to a title shot at the upcoming PPV, while The Steiners were three months away from leaving WWE to go back to WCW. This match only happened once but it is every bit as great as its billing.
Bret Hart and Owen Hart worked 6 untelevised tag team matches against Steve Austin and Mankind in July 1997.
Bret and Owen Hart are not best known for their tag team prowess, which makes this match feel even more like a dream match.The in-ring work outstrips all expectations and is PPV-worthy in its quality, and even an unsatisfying double-DQ/count-out finish doesn’t diminish the quality on show. Bret and Owen Hart would team together until losing to The Quebecers at the Royal Rumble a few weeks later, after which Owen would turn on Bret.
4Shawn Michaels vs Marty Jannetty
Monday Night Raw, July 1st, 1996
As this list recounts things that are largely perceived to be terrible but hide some classic moments, this match comes during Marty Jannetty’s run with Leif Cassidy in The New Rockers. It was very obviously a pale comparison to his original run with Shawn Michaels, the neon colors and leotards were out of touch with the times and this was at a time when the NWO was running rampant in WCW.The disparity in their life trajectories made it feel like Jannetty legitimately had something to prove, the jilted ex-partner taking out his resentment on the WWE Champion.
What is particularly interesting about this match is how it paints Marty as something of a loser in this situation, bitter that he cannot live in the shadow of Shawn Michaels. He doesn’t cut a sympathetic figure, instead, this is just WWE pointedly affirming the gap between their talents, but the believable streak ofhatred and animosity between the two former partners made for a great match.
Marty Jannetty only won one of his four matches with Shawn Michaels, winning the Intercontinental Championship from him on Monday Night Raw on 17th May, 1993.
3Bret Hart vs Hakushi
Monday Night Raw, 24th July, 1994
Furthering his reputation as one of the WWE’s best workhorses, Bret Hart would take part in two matches at the inaugural In Your House event. His match with Jerry Lawler may have taken higher billing on the night, but it was Bret Hart’s match against undefeated Japanese superstar Hakushi that has stood the test of time. Two months later, The Hitman and Hakushi would createa wrestling showcase on many a connoisseur’s list of favorite matches.
Hakushi came from Michinoku Wrestling and is one of the more underappreciated talents of this era. Bret Hart’s technical prowess in this period of his career was so great, that he often would carry matches.Hakushi was one of the few wrestlers who could keep up with the Canadian Wrestling Godand this match is a classic for those who like technically perfect pro wrestling.
2Jeff Jarrett vs Shawn Michaels
In Your House 2, July 25th, 1995
The Intercontinental Championship grew its reputation duringThe Golden Age of Wrestling, but the New Generation had a natural fit to continue that superstar-heavy division in Double J, Jeff Jarrett. Before the guitar-swinging tenure that would go on to define him to a generation, Jarrett was a flamboyant cavalcade of top hats, straps, and flashy ring gear that made him someone fans loved to hate.Jeff Jarrett was Shawn Michaels’s equal in every way here, on a night that produced a legitimate classic.
Full of gravity-defying reversals and thrilling spots, this match isprobably the best match of Jeff Jarrett’s in-ring career. Double J is in spectacular form, raising the bar in a way that Michaels is happy to rise to. This is not only one of the best matches of this era, it is one of the best Intercontinental Championship matches to ever take place.
1Bret Hart vs 1-2-3 Kid
Monday Night Raw, July 11th, 1994
It is a match that is beloved by fans everywhere andthe chances are it’s one of your favorite wrestler’s favorite matches. Both men were hot babyfaces at the time, with Bret Hart trawling the United States as a fighting WWE Champion and Sean Waltman’s 1-2-3 Kid riding the crest of a wave at the start of his in-ring career. It is one of the very first classic Monday Night Raw matches and it will never age.
From the opening handshake and Bret Hart’s iconic look of surprise after Waltman gets the better of their opening lock-up, this is professional wrestling at its zenith.
The exchanges are crisp and the counters are intelligent in their creativity and delivery, with The Excellence Of Execution clearly impressed by the youngster and feeling the moment and the crowd’s red-hot reaction. Bret retained with the Sharpshooter butHart neglected his title and having his hand raised to help 1-2-3 Kid to his feetand lead the applause for the battle-worn contender. It remains one of the best matches in Raw history 30 years on.
