Welcome, everyone. As I’m sure you’re aware, tonight is the 1000th episode of Monday Night Raw. I figure now is as good of a time as any for me to weigh in with my list of the Top 10 Matches in Monday Night Raw history. There’s a lot to choose from, and I’ve done a ton of research for this one in an attempt to not overlook anything. I’ve cross referenced several “best of” lists, DVDs, my own memory, and surveyed friends and fellow fans. Here is my criteria for the Top 10 Monday Night Raw Matches so that we’re all on the same page:

-Had to have happened on one of the 999 previous episodes of Monday Night Raw

-Matches judged on crowd reaction, quality, historic value, and how well they’ve held up through the years…not necessarily in that order.

-It’s impossible to make one of these lists without personal opinions coming into play, so my personal enjoyment does play a factor here. .

These guidelines eliminate any matches that take place in the future, due to my disappointing lack of a time machine. Matches that took place on Monday Nitro, any pay per views, or any episodes of Smackdown also don’t qualify. Terrible matches weren’t considered here, either.

One thing I’ll throw in here: Razor Ramon vs. The Kid isn’t on this list. If this were a list of “Greatest Raw Moments”, it would be a top 3 moment, to be sure. The match was shocking, but the match itself wasn’t great. Instead, there’s a plethora of matches on here that are remembered for their entirety, not just for being an upset. Hopefully that helps further explain what I’m going for with the list.

In previous lists, I’ve attempted to find videos on sites like Dailymotion in an attempt to make the list as accessible as possible to as many people as possible. With apologies, this time around, it’s simply about finding the highest quality clips possible. Next week I’ll get back to being accommodating, but for this list, I don’t want any grainy clips gumming up the works. These are all outstanding matches and should be enjoyed as much as possible, even if it’s only on a computer monitor or mobile device.

Matches that just missed the cut: Shawn Michaels vs. Shelton Benjamin, Triple H vs. William Regal (First Blood), Ric Flair vs. Edge (TLC), Cactus Jack vs. HHH (Falls Count Anywhere) Part 1 Part 2, Kurt Angle vs. Shawn Michaels (Ironman Match)

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Mr. Perfect vs. Ric Flair size=6>



I’ve never been happier to see Ric Flair lose a match.

-Loser Leaves the WWF Match

-Two all time greats

-Far better than any Flair vs. Hennig match in WCW

Ric Flair had great matches in his WWF run, most notably the Royal Rumble in 1992 and his program with Randy Savage. He never felt quite right in this stint there, though. Maybe that’s because I grew up watching NWA so faithfully in the 1980’s, maybe because there were still so many “characters” in WWF in 1992 and Flair just seemed out of place among them. Whatever it was, it had fun moments but never seemed to be clicking on all cylinders to me. Then this match happened. It was a snapshot of what could have been. Both men were still near their physical primes and put on an exhibition here that showed just how far ahead they were of 99% of professional wrestlers. This match looks simultaneously effortless and magnificent. This was early on in the lifespan of Monday Night Raw, and matches of this quality were still few and far between on television. As with the Royal Rumble, the match is enhanced greatly by Bobby Heenan on commentary. I’ve never been happier to see Ric Flair lose a match, because I knew he was headed back to WCW as soon as possible. Flair vs. Sting, Steamboat, and Vader from the following years was completely worth it.

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Owen Hart vs. Davey Boy Smith size=6>



This match is a master class in ring psychology.

-First European Title match

-Tag Team Champions wrestling each other

-Honky Tonk Man on commnentary

For whatever reason, this match didn’t click with me the first time I watched it. I just assumed, from the get go, that they were going to have the British guy win the European title. It just made sense to me. Then he did, and it felt anticlimactic. Going back and watching it now, I realize what I’ve missed out on. This match has received rave reviews from every corner of the internet since it happened, and there’s a good reason for it. This match is a master class in ring psychology. Any worker will tell you that a heel vs. heel match is one of the most difficult matches to pull off, because it so often falls flat with the crowd. In front of a foreign crowd (one of several of these matches to take place outside the US), Davey and Owen provided a perfect blueprint for just such a match. They started out with a show of respect and built from technical wrestling to agitation to more high impact stuff, to a decisive finish. This match was as good as either man ever looked in the ring.

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Chris Jericho vs. Triple H size=6>



People not winning titles against Triple H on Raw has been a theme through the years.

-WWF Championship match

-Dusty-ish finish

-Massive crowd reaction

-Beginning of Chris Jericho as a true main eventer



Moments like this make me miss Chris Jericho as a face. He’s been one of the best heels ever for the last few years now, but he was so much fun as a face when he would go on rants against Stephanie McMahon. Jericho had been an established player in the upper midcard scene, but just hadn’t quite broken through to the main event at this point. Triple H was on fire as a heel here, and the crowd loved Jericho like no other. While Jericho wouldn’t win the WWF Championship here, people not winning titles against Triple H on Raw has been a theme through the years. Jericho would join names such as Buh Buh Ray Dudley, TAKA Michinoku, and Ric Flair as guys that had a potentially huge win pulled away at the last second against HHH. The important part of this, though, was that Jericho turned in an excellent match against HHH and the reaction when he appeared to have won the title was deafening. The message the fans sent was clear – it may not have been Jericho’s time quite yet, but it would be very, very soon.

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Chris Benoit vs. Kurt Angle size=6>



This may be the greatest cage match ever.

-Steel cage match

-Angle’s top of the cage moonsault

-Perfect counterparts in the ring

This may be the greatest cage match ever. Outside of War Games, I can’t think of anything that’s definitively better than this. Don’t get me wrong, I despise what Chris Benoit did, but that doesn’t prevent me from enjoying matches like this that he was involved in. I don’t approve of Jimi Hendrix dying of an overdose, but I can still enjoy The Wind Cries Mary, you know? This match is an interesting watch at this point in history. Angle was coming into his prime as a wrestler, and would remain on that level for a very long time. He and Benoit were perfect foils, and were forerunners of Punk vs. Bryan by a decade. It’s also painful to watch Benoit launch himself from the top of the cage for a flying headbutt now that we know what we do about the condition of his brain. This match has been buried in the vaults for obvious reasons – Angle’s departure and Benoit’s final actions – but it deserves to see the light of day. Regardless of what these men became, this match is one of the all time greats.

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Eddie Guerrero vs. Rob Van Dam size=6>



This match is worth watching again just to see a fan catch a beating.

-Ladder Match

-Intercontinental Title match

-Foolish fan run in

It would be fun to sit down and try to figure out what sort of match Eddie Guerrero and Rob Van Dam could have that wouldn’t be fun to watch. Van Dam, for all of his shortcomings and faults, is almost always entertaining. His run in WWE was full of good matches and great moments. Eddie Guerrero is, of course, one of the all time greats of the ring. He had crowds eating out of the palm of his hand, and giving two high flying guys like this a ladder to work with is a no brainer. As great as it is in and of itself, this match is worth watching again just to see a fan catch a beating. RVD was as over as ever with the crowd as a face, and an audience member seemed to take exception to the possibility that Eddie was about to win the match. He jumped the ring and took a punch in the face from Guerrero, who saw him coming. The run in didn’t break the rhythm of the match, though, and the two men combined to put on a 20 minute classic that ranks highly among the all time ladder matches, as well as the all time great Raw matches.

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Ric Flair vs. HHH size=6>



This was, to me, Ric Flair’s greatest match.

-WWE Championship match

-Great promos to set the match up

-Great atmosphere

I was sitting alone in my dorm in college in Asheville, North Carolina when this match aired. I hadn’t been watching wrestling regularly at this point, because my work and school schedule was so hectic at the time. I had blown off studying on this night and decided to check out Raw. That may have been the best decision of my career as a professional wrestling fan. WWE ran what was, essentially, a one night angle to build to Ric Flair vs. Triple H for the WWE Championship in Flair’s back yard. From the promos throughout the night to the action in the ring, this was, to me, Ric Flair’s greatest match. It came out of nowhere. Flair was on top of his game in terms of promos, he was on top of his game in the ring, and for 10 or 12 minutes, it felt like 1988 again. This match was a time machine, and it took me back to the days that made Ric Flair my favorite wrestler. I turned into a full blown mark again, sitting on the couch in my dorm and screaming for Triple H to tap out when Flair got the Figure Four locked in. I felt gut punched when the match ended. Looking back, this match was about two things – a way to make Triple H look even stronger, and a tribute to Ric Flair. What they created with it ended up being one of the greatest matches in the history of Monday Night Raw.

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John Cena vs. Shawn Michaels size=6>



This match is the ultimate repudiation of any “Cena can’t wrestle” statements.

-2007 PWI Match of the Year

-40+ minutes

-Arguably John Cena’s greatest match to date

John Cena takes a lot of heat on the Internet because he’s marketed mainly to kids and he’s been successful for a long time now. The Internet loves what’s edgy and new, and loves pulling for the perpetual underdogs. One of the biggest criticisms against John Cena is that he can’t wrestle, but this match is the ultimate repudiation of any “Cena can’t wrestle” statements. Is it significantly easier to have great matches against Shawn Michaels than say, Kane? Sure it is. However, it’s not like HBK carried Cena here. Both men played vital parts to the match and they surpassed what was an excellent Wrestlemania match by going for nearly 45 minutes on Raw in London, England. On some level, knowing Cena is capable of these matches makes it even more frustrating that we don’t get them from him more often. Still, the idea that Cena isn’t capable of turning in a classic was forever disproven in this match.

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Mankind vs. The Rock size=6>



This remains one of the genuine feel good moments in the history of professional wrestling.

-WWF Championship Match

-Remembered for Tony Schiavone directing 600,000 viewers to RAW

-1st World Championship for Mick Foley

On January 4th, 1999, WCW made a tremendous error. Call it pride, call it hubris, call it idiocy, call it whatever you like, it was a mistake. It’s hard to blame Eric Bischoff for going ahead with releasing the news, because the strategy had been working for WCW to this point. It simply backfired this time. While that blunder by WCW has become what defines this match, it deserves better. This is better than just a “moment” where WWF took control of the Monday Night Wars. This is better than just a world title change. This is better than DX vs. The Corporation. This remains one of the genuine feel good moments in the history of professional wrestling, and it’s still even better than that. This match was a fun brawl that made the most of the No Disqualification stipulation without getting bogged down by the sheer volume of people involved in it. The Rock was at his arrogant best, Mankind played the underdog role to the hilt, and to quote Mick Foley (who was quoting Pat Patterson), the crowd went banana when he won. The pop when Austin’s music hits is beyond deafening. Michael Cole pulls off one of the greatest calls in wrestling history, remarking “Mick Foley has realized his dream, and the dream of everyone who’s ever been told, “You can’t do it.” Cole losing his voice while he tries to scream commentary over the deafening crowd reaction only adds to things. This is a great match that has become a defining moment in professional wrestling history as well.

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Shawn Micheals vs. Marty Janetty size=6>



Marty Janetty has never been better.

-Intercontinental Title Match

-1993 Match of the Year according to damn near everyone

-One of the first legitimate surprises on Raw

Marty Janetty and Shawn Micheals were partners for 7 years, garnering critical acclaim in both the AWA and WWF for their work against Rose and Somers, The Hart Foundation, and The Brainbusters. They also pulled off maybe the greatest partner split angle in wrestling history when Shawn superkicked Marty through a plate glass window on the Barber Shop segment. Shawn went on to become a fast rising singles star in WWE, and Marty just sort of faded away. Through all those years as a tag team partner before this, and in all the years since, Marty Janetty has never been better. He’s a talented worker that just doesn’t have the natural charisma that Shawn does. That’s nothing to be ashamed of, because very few wrestlers ever have. With the benefit of a surprise appearance to work the crowd up, Marty and Shawn put on a match that was years ahead of its time. That was fitting considering what they had done together as a tag team for the better part of a decade prior to this. This match has received nearly universal praise through the years, and holds up remarkably well nearly 20 years later. Little bonuses in this match include Savage on commentary, Mr. Perfect blocking Michaels’ exit, Sweet Chin Music as a setup maneuver, and a then rare title change on a WWE television show.

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The Two Man Power Trip vs. Chris Jericho and Chris Benoit size=6>



You’ll be hard pressed to find a better match with a hotter crowd.

-Jim Ross and Paul Heyman on commentary

-Four multiple time world champions

-Remembered for HHH’s quad injury

-One of the best tag team matches of the 21st century so far

Some matches are just special. They happen organically. They can’t be predicted, orchestrated, or designed. CM Punk and Daniel Bryan are evidence of this. They’re both great workers, capable of a Match of the Year candidate at a moment’s notice, yet their best matches in 2012 have been against Chris Jericho and Sheamus, respectively. For the match listed here, you’ll be hard pressed to find a better match with a hotter crowd. The only hotter crowds I can remember on Raw were when Flair was challenging for the WWE title in the Carolinas and Bret Hart vs. The Patriot when Bret was on his anti-American kick. Fans genuinely despised the Two Man Power Trip, and Jericho and Benoit were still the darlings of both the IWC and the live crowds at WWE events. The match featured four wrestlers that were a throwback to “old school” wrestling, with an intricate understanding of psychology and how to play each role to perfection. This match was a constant build from the opening introductions, with the stakes getting higher and higher until the crowd was at a fever pitch. The in ring action matched the crowd, slowly and constantly escalating over a period of 20 minutes. One can only imagine how great the match would have been had HHH not infamously blown his quad in this match. Even with that, and maybe partly because of it because it lends an extra bit of historical significance to the match, this match stands alone as the greatest match in Monday Night Raw history…for me.

There you have it. The matches that are, in my opinion, the best that WWE Monday Night Raw has to offer over the course of 999 episodes. Do you think that I left something out? Is something out of order? Gripe about it below. If you gripe, though, give your own list. Hell, you may convince me to see things your way. I’ll keep an eye on the comments and may even join the discussion. I’ll be back here next week for another countdown.

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