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Top 50 WWE Matches from the first 999 RAW episodes

Coming with a top 10 WWE Monday Night RAW matches list sounds easy, but not when you are working off of 1000 episodes. That is when I realized 10 wasn’t going to do it, so in celebration of the 1000th episode I look back at the 50 best WWE matches to take place on RAW!

This was a real fun list to make and the suspects here are pretty obvious names. But it is one guy who came up over and over again that dominates this list and that is Shawn Michaels. While I didn’t intend for this to be a top Shawn Michaels matches list, it may appear to be that way. It isn’t his fault he is so damned good is it?

[adinserter block=”2″]However, Shawn isn’t the only WWE superstar to make magic on Monday Night RAW. A who’s who list of great WWE stars of the last few generations from Kurt Angle to Steve Austin to Edge to The Rock to Bret Hart to Ric Flair to Hulk Hogan to The Undertaker to Chris Jericho and more had some of the best matches of the last 20 years on Monday night.

Keep in mind that these are not ranked in the order of importance. Ranking 50 matches 1-50 is a tough task and one that this writer just didn’t have the energy or time to commit in doing so. If you read the matches you can probably get an idea of what my top five or ten are, and more specifically my favorite one or two. This list was a lot of fun to compile so if you want to add to it or point out anything I may have missed, please leave a comment after reading the post. It really was impossible to rank these in order as it really comes down to personal tastes, so with that said here are the top 50 matches in RAW history in this blogger’s opinion.

Ric Flair vs. Curt Hennig (1/25/93) – This was the Loser Leaves Town match in the Manhattan Center held right before Flair went back to WCW. A fantastic match that saw Mr. Perfect top his former tag team partner.

Mick Foley vs. Terry Funk (05/04/98) – An often forgotten battle of hardcore legends that once took place on WWE RAW which wasn’t their greatest match, but a match certainly of top 30 recognition. Even better, Stone Cold Steve Austin is on commentary for this one.

Shawn Michaels vs. Edge in a Street Fight (02/28/2005) – I loved this match and it amazes me as to how often it is forgotten. This match had it all from excitement to drama to brawling to a fun finish.

Chris Benoit vs. Kurt Angle in a Steel Cage Match (06/11/01) – These guy never had a bad match but this one was exceptional. The moonsault off the top from Kurt is still one of the most memorable moments on RAW over ten years later.

DX & The Radicalz vs. The Rock, Cactus Jack, Too Cool & Rikishi (2/7/00) – This may be my favorite match in RAW history. This match just had something which even today, I cannot put my finger on. Oh yeah, psychology!

Chris Benoit and Chris Jericho vs. Triple H and Austin (05/21/01) – This match is most remembered as the night Triple H tore his quad and kept going, but most forget about what a great match this was before that happened.

The Rock vs. Mankind (01/041999) – Some will say this match is what turned around the Monday Night Wars. Eric Bischoff was kind (and dumb) enough to tell the WCW Nitro audience that this pre-taped match would end with a new WWE champion. The match was great and a lot of WCW fans saw a match they probably would have missed thanks to Tony.

Shawn Michaels vs. John Cena (04/23/07) – Some will say that this was Cena’s best match, although I disagree. This was a rematch of their WrestleMania 23 headliner which was actually much better than their WrestleMania match. This match told a great story and had a great finish that simmered for over twenty-minutes. This one was ranked number one when did a list last year of greatest RAW matches.

Eddie Guerrero vs. Rob Van Dam in a Ladder Match (05/27/02) – This match was a classic! These two guys just went all out in one of the craziest ladder matches on RAW. Like several matches on this list, the match is often forgotten when people talk about great RAW matches in history.

John Cena vs. Rey Mysterio (07/25/11) – To me, this was Cena’s greatest match on RAW and it was all due to Rey. For whatever reason, these guys just had amazing chemistry, and built a heck of a match on free television. I don’t think it is coincidence that Cena hasn’t gotten that match with anyone else.

Bret Hart vs. 1-2-3 Kid (07/11/94) – Going back I think this was one of the most exciting RAW matches in history. These two told a great story and had fans believing at one point that the Kid could actually beat the Hitman as a huge underdog. This was as sound of a technical match as you’re going to see on RAW. I was glad to see this match put on DVD in recent years and acknowledged for its greatness.

Hulk Hogan vs. Ric Flair (05/13/2002) – Hogan and Flair wrestled a lot over the last two decades, but for whatever reason I think this was one of their best matches. Maybe I am a bit partial because of the era I grew up watching wrestling but I absolutely loved this match.

Triple H vs. Chris Jericho (04/17/2000) – This is one of the most memorable matches in RAW history and I do say matches because there were two. This is the famous match in which Jericho won the WWE title early in the show only to have the decision reversed. Both matches were fantastic and the excitement of the crowd made this not only a great match, but one of the most memorable moments in RAW history.

Triple H vs. Taka Michinoku (04/10/2000) – This was a fantastic underdog match that saw Hunter really give fans the idea that Taka could beat The Game. This match was fun, dramatic, had a great storyline, and is still one of my favorites over ten years later.

Steve Austin and The Undertaker vs. Mankind and Kane in a Hell in a Cell match (06/15/98) – This was one of the most exciting matches on RAW during the Attitude Era. The match was held right before King of the Ring to build up the two main-events. The big moment of this action-packed match came when Austin climbed the cage and attacked Kane on top which saw the crowd just got absolutely nuts. Jim Ross in particular is fantastic with the call here.

Triple H vs. Cactus Jack in a Falls Count Anywhere, No DQ Match (09/22/97) – This match had a fun storyline to it which resulted in the return of Cactus Jack. These guys brawled everywhere and it was about as extreme as it got during the Attitude Era and the fans loved it. I hate to go all Michael Cole here but it was truly vintage Cactus Jack in this match.

Razor Ramon vs. 1-2-3 Kid in a $10,000 Match (06/21/93) – Was the match exceptional? Maybe not, but it certainly goes down as one of the most memorable in RAW history. I could see this one not breaking into the top ten, but it is a match that certainly belongs in the top 30.

Steve Austin and Shawn Michaels vs. Owen Hart and Davey Boy Smith (05/26/97) – Austin and Michaels wrestled as hostile partners here against the Hart Foundation. This was a real fun match which blended Austin’s brawling, Michaels high-flying, and the technical wrestling of the tag team champions into a masterpiece.

John Cena and Shawn Michaels vs. Batista and The Undertaker (03/26/2007) – This rare gem came to Madison Square Garden a week before WrestleMania and the rabid New York fans were ready. The match is noteworthy for the rare interaction between Cena (who the fans hated) and The Undertaker.This match had a real fast pace, a ton of intensity, and a fantastic atmosphere thanks to the New York crowd.

Bam Bam Bigelow vs. Bret Hart (aired 07/26/93) – This was a rare “big-time” main-event to air on RAW during the time period. The match headlined the 100th RAW episode.

Taka Michinoku vs. The Great Sasuke (07/07/97) – This was hardly their best match, yet for RAW it was awesome. These two Michinoku Pro rivals were rematched coming off the Candian Stampede show. If you like high-flying, action-packed matches, you’ll love this one.

Jerry Lawler vs. The Miz in a TLC Match (11/29/10) – I never would have expected The Miz to make a list of great anything but this match was really special. The Philadelphia crowd was 100% behind Lawler which made the atmosphere here one of the best in RAW history.

Dolph Ziggler vs. Randy Orton (11/28/11) – Some have said that this is the best Randy Orton match of his career. I don’t know if I’d go that far, although It is hard to argue that statement after watching this match.

Dolph Ziggler vs. CM Punk (11/21/11) – Talk about two guys who have great chemistry? This was Punk’s first match off his title win at Survivor Series and it was fantastic.

Ric Flair vs. Edge in a TLC match (01/16/06) – Ric Flair is a crazy s.o.b.! You can never go wrong with Ric Flair challenging the world champion in his home town. Flair’s family is at ringside and Edge has crazy heat as the new heel world champion beating down Flair in his home town. It doesn’t get much better than a bloody Ric Flair putting Lita in a figure-our leg lock.

Edge vs. Jeff Hardy (08/21/06) – This is one of the most underrated matches in RAW history. Jeff made his return on RAW that night, confronting Edge earlier in the show. The Coach made the match and the fans just ate it up!

Steve Austin vs. The Big Show with Mankind as the special guest referee (1999) – The Rock is on commentary here and the match features one of Show’s first matches after signing with the WWE which made this something of a “Dream Match”. Vince McMahon sat ringside, Steve Austin is on fire, and the fans were electric in this pre-WrestleMania grudge match. The match also features a great post-match brawl with Austin and Rock.

The Rock vs. The Hurricane (03/10/03) – The Rock was at his best during this time period as Hollywood Rock. Rock and Hurricane had a confrontation backstage and the match was made. The match is tremendous and one of the most exciting in RAW history as the underdog Shane Helms comes within inches of pulling off the biggest upset in RAW history.

Hulk Hogan and The Rock vs. N.W.O. (03/18/02) – This was a 2-3 match featuring arguably the most legendary tag team to ever partner up on Monday Night RAW. The match came on a hot night as part of the Draft Lottery special.

Shawn Michaels vs. 1-2-3 Kid (03/04/96) – Talk about two guys that went out there and tore the house down. This is a fantastic match which features a ton of action and all of the high-spots you’d expect from these two. I was pleasantly surprised to see it acknowledged years later on one of Michaels’ DVDs.

Chris Jericho and Christian vs. Shawn Michaels and Jeff Hardy in a No DQ Match (02/17/03) – Talk about a real fun match that fell through the cracks over the last few years. This match is every bit as good as you’d think it would be and then some.

Bret Hart vs. Steve Austin in a Street Fight (04/21/97) – Any time you get Austin and Bret in the ring you are going to have a fun match. This was a really exciting match that came the night after Revenge of the Taker. Austin winds up injuring Bret’s knee here in an exciting but relatively short match considering who was involved.

Marty Jannetty vs. Shawn Michaels (05/17/93) – This was the 1993 Match of the Year and with good reason. This was a fantastic match that was probably a few years ahead of its time.

Shawn Michaels vs. Owen Hart (12/29/97) – Owen Hart is back and seeking revenge for his brother Bret following the Survivor Series Montreal Screwjob. Owen shows a more aggressive side here in a real hot back and forth match.

Bret Hart vs. Psycho Sid in a Steel Cage Match (03/17/97) – I have always felt that this was the true beginning of the Attitude Era. The match is just a lot of fun with Steve Austin constantly interfering in Bret’s behalf with the idea being that Austin wants Bret to remain champion for their match at WrestleMania 13. The aftermath is just as exciting as the match with a real heated moment between Bret and Vince McMahon which sees the Hitman snap.

Trish Stratus vs. Lita (12/06/04) – Trish wears a face mask here after Lita broke her nose. This was a RAW main event which sounds unheard of in 2012 but the fans were really into Lita vs. Trish. This was just a great match with a lot of big moves including a super-plex off of the top rope.

Bret Hart vs. Owen Hart (11/25/96 – This was the usual great Bret vs. Owen match. Bret returned to RAW after a long hiatus here and didn’t miss a thing against his “evil” baby brother.

Triple H vs. William Regal in a First Blood Match (08/02/04) – Like several matches on the list, this is an often forgotten classic. Triple H bloodied Regal to a pulp in this tremendous battle. This was done during the Eugene-Hunter feud and was in my opinion the best Regal match ever in the WWE.

Edge vs. Matt Hardy in a Loser Leaves Raw “MITB” Ladder Match (10/03/05) – How can you go wrong when you have a Hardy and Edge in a Ladder Match (or any match for that matter)? You can’t and these guys delivered the finale to one of the most intense feuds of the fall of 2005 live on RAW.

Ric Flair vs. Triple H (5/19/03) – How can you go wrong with Ric Flair challenging for the world championship in Greenville? You can’t and maybe that is why Hunter picked him as his opponent. It certainly wasn’t Flair’s greatest match but the crowd, the time period, and the intensity between Flair and Hunter put this one on the list.

Kurt Angle vs. Shawn Michaels in an Iron Man Match (10/03/25) – Surprisingly this one is also easily forgotten when people recollect great RAW matches of the last 1000 episodes. This was a part of the Homecoming show and saw two of arguably the greatest wrestlers at that time go at it non-stop for 30-minutes in an absolute classic.

Shawn Michaels vs. Shelton Benjamin (5/2/05) – This was part of the Gold Rush tournament and surprised a lot of people with how great of a match it turned out to be. Of course the memorable moment here is Michaels catching Benjamin off of the ropes with Sweet Chin Music for the finish.

Owen Hart vs. Davey Boy Smith (03/03/97) – The finals for the European championship saw partners and friends clash for the first time on RAW. This was about as technical a match as you’ll ever see on RAW and an absolute masterpiece.

Chris Benoit vs. Triple H Iron Man Match (07/26/04) – Iron Man matches on RAW are rare, but one-hour Iron Man matches on WWE television are even harder to come by. This was one of the few to ever make Monday night (I can’t think of any others) and it really showcased the great psychology Hunter and Benoit had in the ring together.

Rob Van Dam vs. Edge vs. John Cena (07/03/2006) – The bad news is that RVD just got busted and had to drop the WWE championship. The great news is that WWE fans got a match for free that they normally would have had to pay to see on pay per view. Even better news was that the match was tremendous!

The Undertaker vs. Jeff Hardy in a Ladder Match (06/01/2002) – This should really be called the Jim Ross call because as great as this match was, it was Jim Ross’ commentary and his cheer leading for Jeff that landed this one in the top 30. Can an announcer make a difference? Listen to this match and I dare you to tell me he or she can’t. It also didn’t hurt that Hardy had the match in his home town.

Jeff Hardy, Matt Hardy, and Lita (Team Extreme) vs. Stephanie McMahon, (The Two Man Power Trip) Triple H, and Steve Austin (09/04/01) – Hunter and Austin did a tremendous job of elevating the Hardy brothers and making people believe that they could actually hang with the big boys. I know that there was a lot of criticism over the finish of Steph pinning Lita, but the actual match was a lot of fun to watch.

[adinserter block=”1″]Shawn Michaels vs. Triple H (12/29/2003) – Hunter and Michaels had arguably the best series of matches in the business during this time period and the WWE capitalized on it by closing out 2003 with arguably their best. This match was just a fantastic back and forth match that was very reminiscent of the old Steamboat-Flair matches (by design as they even copied the headlock spot) and is still remembered almost ten years later as one of the best.

Shawn Michaels vs. Chris Benoit (02/16/04) – Here is another (see a pattern) forgotten RAW classic. This match came during a time in which Evolution was feuding with Benoit. This was as good as a match as you’d expect from these two in 2004 and then some. This one had a lot of near falls and really got hot towards the final minutes of this 21-minute bout.

Kurt Angle vs. Steve Austin (January 18, 2001) – There was a huge buildup for this match with Austin getting a rematch at the WWE championship. Austin was the heel here against America’s hero and a very popular Angle at the time. This was an intense back and forth match marred by a real disappointing finish (probably why most people forget about this one).

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  1. I don't remember the year but the Undertaker had his ministry. The Undertaker and HHH in a handicap match against the Rock. They beat the crap out of the Rock for most of the match, but in the end the Rock laid the smack down. Great match!

  2. With all due respect, but how can you even put John Cena into this list? The man can not wrestle!!!!! He is a poser. Im surprised you didnt have anything with Taz or more things with Cm Punk. I understand this is your list but I was disappointed to see John cena in this at all. and the match between mysterio and cena was a joke. Rey wrestled 3 matches that night and Cena was fresh. Is that really his best match on raw? What about the match between shawn michaels and cena with a 1 hour time limit? im just saying dude. Raw has had better moments and matches.

    • I am hardly a John Cena fan but what is he posing? As a wrestler? I am not a fan at all but his matches, specifically with Rey were very good. And the match with Michaels is on the list so what's your gripe? On the one hand you dont like him on the list and then you tell me a match of his that should be on….which is actually on the list LOL.

      So as I said in the blog, give me a few matches I missed that were better than these 50? Id love to hear them.


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