5 Most Important Matches In WWE Monday Night Raw History

Man, what happened to Monday Night Raw? I know the pandemic has put constraints on everybody, but even before then, what happened to the must-see nature of the program? Two of the three most-watched Raw episodes in 2019 were the post-WrestleMania show (typical) and the "Raw Reunion" show where the heroes of the 50+ demo took another victory lap. These days, Raw's viewership skews older, while plunging to new depths (the tune out in the latter likely aids the former).

It used to be that Monday nights were destination television for wrestling, but with Wednesday's combined AEW/NXT viewership total creeping up on Raw as Raw sinks, you wonder what WWE can do to right its flagship. Advertising matches in advance (like Randy Orton vs. Big Show) and trying to create post-PPV intrigue (Rey's eye and the Sasha/Asuka controversy) don't seem to be helping all that much.

Well here's a piece that might appeal to the 50+ demo: a look back at five extremely important matches in Raw's 27-and-a-half year history, each for their own reasons.

Man, what happened to Monday Night Raw? I know the pandemic has put constraints on everybody, but even before then, what happened to the must-see nature of the program? Two of the three most-watched Raw episodes in 2019 were the post-WrestleMania show (typical) and the "Raw Reunion" show where the heroes of the 50+ demo took another victory lap. These days, Raw's viewership skews older, while plunging to new depths (the tune out in the latter likely aids the former).

It used to be that Monday nights were destination television for wrestling, but with Wednesday's combined AEW/NXT viewership total creeping up on Raw as Raw sinks, you wonder what WWE can do to right its flagship. Advertising matches in advance (like Randy Orton vs. Big Show) and trying to create post-PPV intrigue (Rey's eye and the Sasha/Asuka controversy) don't seem to be helping all that much.

Well here's a piece that might appeal to the 50+ demo: a look back at five extremely important matches in Raw's 27-and-a-half year history, each for their own reasons.

5. Razor Ramon Vs. The 123 Kid (1993)

The WWF tagline used to be, "Anything can happen in the World Wrestling Federation," and that proved to be the case in May of 1993. Young Sean Waltman was presented as an enhancement talent for weeks, getting soundly beaten by various midcard heels.

When he matched up with Razor, it appeared to be just another squash. That was, until Kid took advantage of a missed corner charge, then Moonsaulted onto Ramon to score the upset of the century. The match was a lesson to fans in not taking an outcome for granted.

5. Razor Ramon Vs. The 123 Kid (1993)

The WWF tagline used to be, "Anything can happen in the World Wrestling Federation," and that proved to be the case in May of 1993. Young Sean Waltman was presented as an enhancement talent for weeks, getting soundly beaten by various midcard heels.

When he matched up with Razor, it appeared to be just another squash. That was, until Kid took advantage of a missed corner charge, then Moonsaulted onto Ramon to score the upset of the century. The match was a lesson to fans in not taking an outcome for granted.

4. Trish Stratus Vs. Lita (2004)

A full 10 years before the advent of WWE's Women's Revolution, Stratus and Lita got the main event slot on Raw, in a battle for Stratus' Women's championship. Lita won what turned out to be a very good match, but there was greater significance here.

While women had gone on last on Raw before (Lita vs. Stephanie in 2000, for example), this match was a straight-up exhibition of two talented women as no-frills wrestlers. It was a rare concession in the "Diva" era that women could deliver big in an advertised main event.

4. Trish Stratus Vs. Lita (2004)

A full 10 years before the advent of WWE's Women's Revolution, Stratus and Lita got the main event slot on Raw, in a battle for Stratus' Women's championship. Lita won what turned out to be a very good match, but there was greater significance here.

While women had gone on last on Raw before (Lita vs. Stephanie in 2000, for example), this match was a straight-up exhibition of two talented women as no-frills wrestlers. It was a rare concession in the "Diva" era that women could deliver big in an advertised main event.

3. John Cena Vs. Shawn Michaels (2007)

While Triple H and Chris Benoit had already graced Raw with a 60-minute Iron Man match, most would concur that Michaels and Cena outdid them three years later in their standard one-fall match at London's Earl's Court. Arguably, it was Cena's best match ever to that point.

When you put on a one-hour wrestling match on free TV (especially when you haven't advertised how long it's going to go), you're assuming a great risk for many reasons. The match ended up being one of the greatest in Raw history, a pleasing slice of something unexpected.

3. John Cena Vs. Shawn Michaels (2007)

While Triple H and Chris Benoit had already graced Raw with a 60-minute Iron Man match, most would concur that Michaels and Cena outdid them three years later in their standard one-fall match at London's Earl's Court. Arguably, it was Cena's best match ever to that point.

When you put on a one-hour wrestling match on free TV (especially when you haven't advertised how long it's going to go), you're assuming a great risk for many reasons. The match ended up being one of the greatest in Raw history, a pleasing slice of something unexpected.

2. Steve Austin Vs. Vince McMahon (1998)

Eighty-three long weeks. Since June 1996, WCW Monday Nitro kept Raw underfoot, taking control of the Monday Night Wars with a hipper, fresher product, and riding that momentum quite a long ways. Then Vince stumbled onto the perfect antidote - himself as lead heel.

McMahon was still semi-neutral when the night started on April 13, 1998, but when enemy Stone Cold goaded him into accepting a match against him, the tide began turning. Raw ended up winning the night on the intrigue of a match that never even truly took place.

2. Steve Austin Vs. Vince McMahon (1998)

Eighty-three long weeks. Since June 1996, WCW Monday Nitro kept Raw underfoot, taking control of the Monday Night Wars with a hipper, fresher product, and riding that momentum quite a long ways. Then Vince stumbled onto the perfect antidote - himself as lead heel.

McMahon was still semi-neutral when the night started on April 13, 1998, but when enemy Stone Cold goaded him into accepting a match against him, the tide began turning. Raw ended up winning the night on the intrigue of a match that never even truly took place.

1. Steve Austin Vs. The Undertaker (1999)

When we all pore over the viewerships and demos and ratings of today's wrestling shows, let's keep this in mind: Stone Cold winning his fourth WWF title by defeating Undertaker in June 1999 set a cable TV wrestling mark that will never, ever be sniffed.

At one point late in the bout, the Austin/Undertaker match had 10.7 million viewers. Take a moment and let that number sit. It was the first wrestling match in cable history to even break *seven* million viewers, and did an ungodly 9.5 rating with a 17.1 share. Man, those were the days.

1. Steve Austin Vs. The Undertaker (1999)

When we all pore over the viewerships and demos and ratings of today's wrestling shows, let's keep this in mind: Stone Cold winning his fourth WWF title by defeating Undertaker in June 1999 set a cable TV wrestling mark that will never, ever be sniffed.

At one point late in the bout, the Austin/Undertaker match had 10.7 million viewers. Take a moment and let that number sit. It was the first wrestling match in cable history to even break *seven* million viewers, and did an ungodly 9.5 rating with a 17.1 share. Man, those were the days.