The Greatest Moments in WWE Monday Night Raw History

Since its debut in 1993, Monday Night Raw has delivered some of the most noteworthy moments in wrestling history. Some good, some great, some very questionable, some we’d truly wish to erase from our memories (the Attitude Era was A LOT).

However, what is undeniable, is that WWE’s flagship show has delivered in spades over the last three decades. Since those early days at the Manhattan Centre, Raw has taken us on an emotional rollercoaster. From Bret Hart bangers to beer baths. Mick Foley miracles to Milk-A-Mania. Dramatic debuts to gut punching goodbyes.

From the Monday Night Wars through Ruthless Aggression fuelled Brand Splits all the way to the modern day, Raw has already provided enough head spinning moments and matches to last another 30 years.

But with next week’s monumental 30th anniversary show on the horizon, what are the greatest moments in the show’s history?

Well, a whole (non-exhaustive) bunch of them have been compiled for your nostalgia driven pleasure right here.

There’s plenty that haven’t made the cut, obviously. But even so, this trip down memory lane is still a wild ride. So here are just a few of Monday Night Raw’s greatest hits.

Roman Reigns Declares That WWE Is His Yard Now

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Over the last two-and-a-half years, the whole wrestling world has belonged to Roman Reigns. The Tribal Chief is not just Monday Night Raw’s premiere villain. He’s one of the biggest and best characters to ever grace the show.

But before his record breaking run started back in the second half of 2020, the WWE Undisputed Universal Champion was The Big Dog. And his legacy wasn’t as assured. Although his actions on Monday Night Raw on 3rd April, 2017 went a long way to cementing him as a legend.

The night before, at WrestleMania 33, Reigns had handed The Undertaker only his second ever ‘Mania defeat. It was believed to be ‘Taker’s final match. Reigns had effectively retired him. And the Monday Night Raw crowd in Orlando that spring evening hated him for it.

Instead of shying away with the molten negative reaction, Reigns revelled in it. For 10 minutes. He stood there. Basking in his glory (sorry, Keith Lee) while over 10,000 people lost their minds. Then, after showering in the abuse, he dropped five immortal words that would immediately enter into Monday Night Raw history.

“This is my yard now”.


The 1-2-3 Kid Arrives

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OK, so this is technically two moments/matches. But one can’t really exist without the other. Sean Waltman, who would later achieve his greatest fame as part of Hall of Famers and Attitude Era lynchpins DX, shocked the world on 17th May, 1993 when he moonsaulted his way to a stunning upset over Razor Ramon.

And while that match was no doubt a monumental moment in itself, what would follow in the near future was even more impressive.

Just over a year later, the Kid was going toe-to-toe with the Champ. On 11th July, 1994, Waltman challenged Bret ‘The Hitman’ Hart for the WWF Championship. The match was an instant classic that still holds up almost 30 years later.

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The two matches made the Kid a star and, after a couple of years as part of the nWo over in WCW, he was back as X-Pac in 1998. Many more memories were to follow, along with a few runs with the European and Tag Team Titles. And, of course, a prominent place in one of the most iconic factions of all time.

Mrs.Foley’s Baby Boy Becomes WWF Champion

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“Yeah that’ll really put butts in seats”. So came the now infamous call from Tony Schiavone on WCW Nitro. Of course, the decision to use this line as a way to denigrate Mick Foley and his historic WWF Title victory was not Schiavone’s call. But rather a ratings mad Eric Bischoff, now several consecutive weeks into the losing side of a war he would never be on the victorious side of again.

The tactic was designed to deter any of Nitro’s viewers from watching a recorded episode of Raw that fateful Monday night. Instead, the commentary had the opposite effect. Hundreds of thousands of wrestling fans decided they wanted to see the former Cactus Jack’s seismic win over The Rock.

As the masses flipped the channel, Stone Cold Steve Austin flipped the script on The Corporation. An earth shattering entrance into the chaos of the Monday Night Raw main event on 29th December, 1998 generated a pop so loud it could be heard from space. A chair shot to the dome of The Corporate Champ and Mrs.Foley’s baby boy was perhaps the most unlikely WWF Champion in history.

Triple H Returns From Injury In Madison Square Garden

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There’s never a good time to endure a major injury. But Triple H’s quad tear in May 2001 was particularly grim timing. The then World Wrestling Federation was on a major roll, WCW was dead and the invasion angle was upon us. A now heel Steve Austin needed opponents. Triple H was reportedly earmarked as one of those opponents.

Then The Game’s quad explodes during a classic tag team match on Monday Night Raw and the next eight months are spent on the shelf. No major rivalry with Austin, no part to play in the doomed invasion angle, which could have potentially helped the situation.

Fast forward to January 2002. Madison Square Garden. One of the most hotly anticipated returns of all time. In kicked Motorhead and out came the denim topped leather. New York City almost imploded with the ovation. Over 20 years later and we still get goosebumps watching this.

Click the next page to see the rest of our picks for The Greatest Moments in WWE Monday Night Raw History.