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WWE Monday Night Raw: Ranking the 25 Best Matches in Raw History

Ryan DilbertWWE Lead WriterJuly 3, 2012

WWE Monday Night Raw: Ranking the 25 Best Matches in Raw History

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    Since 1993, WWE's Raw has been the home for wacky moments, stirring promos and some of the best matches in the company’s collection. 

    Tag team battles, championship bouts and ladder matches all highlight the long-running show's greatest wrestling wars. 

    You will see several names repeat on this list.  Chris Benoit, Mick Foley, Kurt Angle and Bret Hart have contributed a glut of classics to Raw's history. 

    Shawn Michaels appears here an astounding nine times. 

    Who will make their way onto this list in the coming years?  Daniel Bryan, CM Punk, Dolph Ziggler and Cody Rhodes could soon shove many of these battles aside and replace them with their own.

Honorable Mention-May 4, 1998: Mick Foley vs. Terry Funk-Falls Count Anywhere

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    This gritty brawl pitted friend against friend, Hardcore Legend against Hardcore Legend. 

    Mick Foley traded chair shots and right hands with Terry Funk as Steve Austin added his thoughts on commentary.  All the wild action and violence you'd expect from Funk and Foley is here, from a piledriver on a chair to slugging it out in the crowd. 

    Austin's hatred of Foley, as well as his magnetic personality, added depth to the match. 

    Eventually Austin, and later Mr. McMahon, got involved.  The multi-person interweaving feuds of that period gave Raw a never-ending feeling of compelling tension.

25. July 24, 1995: Bret Hart vs. Hakushi

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    Bret Hart's run as the No. 1 guy in the company gave many a man the match of his career.  Hakushi's highlight reel is a short one, but he and Bret put on a work of art.

    The throwback match featured classic tenets like an interfering manager, clear heel and face roles and stereotype-centered gimmicks.

    The Hitman sold so well that night that he made standard moves look like they were devastating him. 

    Hakushi made for an intriguing bad guy, vicious and nimble.  His cartwheels and flips were stunning. 

    Dominated for much of the match, Bret looked every bit the resilient hero by the end of this entertaining encounter. 

24. April 30, 2007: Edge vs. Randy Orton

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    Edge and Randy Orton managed to pack a bevy of energy and aggression into this shorter match. 

    Rated RKO was falling apart by this point, but wouldn't officially disband until May of that year.  Their palpable hate throbbed on the screen.

    Their chemistry made every move seem natural and every counter smooth.

    A mid-air dropkick, Orton crashing into the announce table and frantic near-falls highlighted the action. 

    A bloodied Orton lost and Edge would soon move to SmackDown and become the World Heavyweight Champion.

23. April 12, 2004: Evolution vs. Shelton Benjamin, Benoit, Foley and Michaels

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    Evolution took on the newly crowned World Heavyweight Champion Chris Benoit and a team loaded with stars. 

    In a match that might have seemed too crowded with egos and bodies, everything clicked.  The fans were loud throughout, elated at every chop and helped elevate the action with their energy.

    Every guy got a chance to shine and given such a short time to work with, they held nothing back.  The match managed to sustain its steamrolling momentum until it unraveled into a brawl.

    The instant classic was capped off by a scintillating Sweet Chin Music on Randy Orton.

22. Jan. 16, 2006: Edge vs. Ric Flair-Tables, Ladders and Chairs Match

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    One of Raw's bloodiest matches had fans holding their breath wondering if the legendary Ric Flair would actually be able to win the WWE Championship one more time. 

    Flair was on a roll, his career gaining a second wind. 

    He took on the master of the TLC Match and looked damn good in the process.  At one point, he grabbed Edge's testicles and squeezed them in a claw-like maneuver.

    The action was brutal and dramatic.  Flair's daughter looked on; screaming, pleading and adding to the emotion of the match. 

21. Jan. 7, 2008: Jeff Hardy vs. Umaga-Cage Match

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    Jeff Hardy battled the monster, Umaga, in a showdown of grace vs. power and good vs. evil. 

    Raw Roulette had them fight over the Intercontinental Championship in a steel cage.  Randy Orton paced outside, anxious and angry. 

    Orton tossed in a number of steel chairs in the hopes that Umaga would crush Hardy with them, but Hardy ended up using them as a springboard and later zipping one at Umaga's face. 

    As dominant as Umaga was at times, manhandling Hardy, Hardy came out the victor, thanks in large part to an audience-stunning Whisper in the Wind.

20. April 10, 2000 :Triple H vs. Taka Michinoku

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    A lesser known gem started out with Triple H not knowing who he'd be defending his WWE championship against.  His surprise opponent was the Japanese spark plug, Taka Michinoku. 

    With the Acolytes at ringside as Michinoku's insurance policy, the match moved along at a rapid pace.  Triple H hasn't often worked with guys as quick and agile as Michinoku, and the unexpected chemistry they had was wonderful to watch. 

    Throw in a defiant Earl Hebner and a rabid crowd, and this match had the feel of a classic early.

    The chaos at the end, Kaientai and the Acolytes interfering, the McMahons getting involved, was indicative of how Raw felt at that time.  Anything could happen.  We felt like were sitting on a fault line and it rumbled every Monday. 

19. Feb. 15, 1999: Rock vs. Mankind-Ladder Match

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    The Raw archives feature plenty of work from The Rock and Mankind.

    Their usual thrilling chemistry was heightened by the addition of a ladder and Steve Austin on commentary and the WWE Championship being up for grabs.

    The match featured all the chair, steps and ladder violence you'd expect.

    They brawled like they do so well, causing a barricade to collapse in the crowd and the audience to lose their voices.      

18. Feb. 7, 2000: Triple H & the Radicals vs. Cactus, Rock, Rikishi, 2 Cool

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    Much of this match is just chaos with every wrestler involved fighting in and out of the ring at the same time.

    The Rock and Cactus Jack were supposed to be on their own, but Rikishi and Too Cool joined them to even things up. 

    The energy from the crowd is phenomenal.  Their spirited reaction to everything elevates the match. 

    Ignore Stephanie McMahon's terrible commentary and the weird ending where the non-legal man gets pinned for the loss and instead focus on the wildness and the deliciously volatile nature of this showdown. 

    Kane's return from a hand injury is the proverbial icing on the cake. 

17. Jan. 22, 2007: Shawn Michaels vs. Edge-Street Fight

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    The go-home episode before 2007's Royal Rumble featured a number of good matches, but the main event was on another level. 

    Ribs cracking on ladders, blood, belts and chains made for an intense clash between two WWE Hall of Famers. 

    This Street Fight showed off the violent sides of both men.  The action got ugly fast as Shawn Michaels yanked off his belt and started whipping Edge.

    So many moments in the match had fans wincing. 

    They pounded on each other until a bruised-faced Randy Orton sneaked in and RKOed Michaels. 

16. Feb. 16, 2004: Chris Benoit vs. Shawn Michaels

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    With the magnificent performance that Chris Benoit and Shawn Michaels put on, you would have thought they'd worked together for years.

    They had instant chemistry, melding aggression with skill beautifully. 

    Benoit and Michaels battled over who would be the number one contender for Triple H's World Heavyweight Championship.  As we know now, both men would fight for the title against Triple H at WrestleMania XX.

    This was a prelude to that ultimate classic.

    Their Raw match featured chest-reddening chops, suplexes galore and the drama of Michaels fighting desperately to escape the crossface.

15. May 27, 2002: Rob Van Dam vs. Eddie Guerrero-Ladder Match

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    It may be hard to remember when Raw featured Ladder Matches, but it may be even harder to remember when wrestlers fought so fervently for the Intercontinental Championship.

    This clash between Eddie Guerrero and Rob Van Dam began with a quick pace, both men dodging and kicking until their match devolved into a brawl.

    Bone smacked against steel again and again.  Both RVD and Guerrero took big risks which helped tell the story as much as it excited the fans. 

    Chris Benoit bought a ticket to sit ringside and tension began to build.  In the end, Benoit and Steve Austin got involved and Raw's enjoyable chaos ensued.

14. March 27, 1995: Bret Hart vs. Owen Hart-No Holds Barred

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    WWE had the good fortune of having two immensely talented brothers on their roster. 

    Owen and Bret's lifetime of familiarity gave their matches the benefit of excellent chemistry as well as the unparalleled drama of brother warring against brother.

    Their hatred is especially convincing in this match, which in many ways is more of a fight than their other battles. 

    Bret held onto the Sharpshooter after the bell rang, Jim Ross was masterful and the ropes rattled in this masterwork.

13. Sept. 29, 2003: Christian vs. Rob Van Dam-Ladder Match

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    Two masters of the Ladder Match came together to create one of the best Intercontinental Championship matches in history. 

    Both Christian and Rob Van Dam produced some highly creative spots.

    Their match was a story of two men willing to suffer through anything to win; falling, crashing and grinding their way to the finish line. 

    RVD provided an exciting finish courtesy of a five-star frog splash from the top of a ladder. 

    With as dramatic and meaningful as the wrestlers made this match feel, the title change felt monumental.

12. Dec. 29, 2003: Triple H vs. Shawn Michaels

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    Of the many battles in the Triple H and Shawn Michaels rivalry, this one might get overshadowed by their street fights and Last Man Standing type matches, but is one of their better straight wrestling matches on Raw or anywhere.

    Set in Michaels' hometown of San Antonio, this saw their usual excellent chemistry coupled with some vintage Ric Flair dirty tactics. 

    The Heartbreak Kid kicked the second rope into the Game's nether region and dove onto both Flair and Triple H on the outside. 

    Throw in a surprisingly fair officiating job by Eric Bischoff, and it's no wonder the crowd was so keyed up as the climax hit. 

11. July 11, 1994: Bret Hart vs. 1-2-3 Kid

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    One of the most masterfully told stories in a ring on Raw came when the upstart 1-2-3 Kid (Sean Waltman) stood toe to toe with Bret Hart on an episode of Raw in its second year.  

    After Waltman had beaten Razor Ramon, fans wondered if he could do the impossible and pull off the ultimate upset. 

    This is a story of mutual respect and sportsmanship.  This is a clinic on how to perform a crisp, precise match. 

    Waltman's beautiful kicks paired with Bret's technical skill make this just a delectable show to watch.  Bret took Waltman to a level he'd never experience again, flirting with a five-star rating. 

    Every move has the crowd in Waltman and Bret's hands; every near-fall sends shivers down fans' backs. 

10. Aug. 2, 2004: Chris Benoit, Edge and Chris Jericho vs. Evolution

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    The volatile energy of this six-man tag match exploded early, beginning with Edge choking Randy Orton with his jacket. 

    For most of the match, it felt the action was on the verge of complete chaos. 

    As Ric Flair and Chris Benoit traded vicious chops, as Batista bulldozed through his opponents and Chris Jericho injected speed and excitement, the rumbling of drama seemed to grow louder and louder. 

    As a set-up for Benoit and Orton's World Heavyweight Championship at SummerSlam, Orton was made to look vicious here, a merciless predator. 

9. May 2, 2005: Shelton Benjamin vs. Shawn Michaels

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    While this match is more famous for the thunderous superkick that ended it, there was in fact an all-time great match that preceded that move.

    Raw hosted the Gold Rush tournament, a way to determine who would face the then-World Heavyweight Champion, Batista.

    Shelton Benjamin faced a surprise entry in Shawn Michaels.

    Benjamin shined in the spotlight, his big-time athleticism on display.  Both men delivered some sick kicks and the match was littered with near-falls. 

    After Michaels scored the win, there was a touching moment where he showed Benjamin respect by leaning over him and checking on him.   

8. Oct. 7, 2002: Four-Way Tables, Ladders and Chairs Match

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    The first TLC match on Raw featured a number of TLC veterans, namely Bubba Dudley, Jeff Hardy and Christian. 

    Kane went it alone in the four-team battle for the tag titles because his partner, Hurricane Helms, was injured.   

    In a flurried affair, more wild carnage than story, Chris Jericho and the talented guys working with him produced a certifiable slobberknocker. 

    With everyone flying around and weapons smacking on flesh, a thrill ride was inevitable.

7. May 3, 2004: Shawn Michaels vs. Chris Benoit

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    After they'd battled a few months back on Raw and at WrestleMania XX, Shawn Michaels and Chris Benoit went at it again.   

    This encounter bested their last one on Raw by having more at stake, by being more intense and being buoyed by more energetic crowd. 

    The newly crowned World Heavyweight Champion fought in a fiery battle, entangled with Michaels, never relenting. 

    It felt like the match could end at any moment.  Michaels slipped out of several crossfaces and Benoit avoided several Sweet Chin Musics.  Michaels threw in a Walls of Jericho for good measure. 

6. March 31, 1997: Davey Boy Smith vs. Owen Hart

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    The finals of the tournament finals to determine the first-ever European Champion pitted two brothers-in-law and the tag team champions at the time against each other.  

    Battling in front of fans in Berlin, Owen Hart and the British Bulldog crafted a marvelous technically sound match teeming with emotion.

    The tension had been building between Hart and Smith long before this.  The match featured multiple staredowns, the two men feeling each other out, patiently building up the drama. 

    Hart and Smith fought at a grinding pace with bursts of frantic action.

    They traded nifty counters and shifts in momentum until Smith finally came out on top.

5. June 11, 2001: Kurt Angle vs. Chris Benoit-Cage Match

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    Kurt Angle and Chris Benoit have used their near-perfect chemistry to construct a mountain of classic matches.  This has to rank highly on their list of great performances.

    A suplex surplus was aided by the brutality of the cage. 

    Two big spots stand out amongst all the grueling grappling.  The first is Angle missing a moonsault from the top of the cage. 

    The other has Benoit ready to escape with the cage, but Steve Austin is waiting for him on the floor, a rabid dog with a steel chair.  Benoit decides to turn around and deliver a headbutt off the cage.

4. Oct. 3, 2005: Shawn Michaels vs. Kurt Angle-30 Minute Iron Man Match

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    As Kurt Angle walked down the aisle, Jim Ross said, "Take a deep seat, ladies and gentlemen.  You're about to see a classic."

    How right he was.

    Convincing strategy and immense star power made this Iron Man match an unforgettable battle.

    Shawn Michaels started the action off with an offensive flurry, but soon Angle was wearing down Michaels with his strength advantage.    

    Fans saw Angle deliver an Angle Slam on the outside and an Angle Slam from the top rope.  Innovation and desperation were hallmarks of his match. 

    Michaels bit Angle's head.  The two men countered each other to the delight of the crowd. 

    Neither man's will could overpower the other's and when the clock ran out, nothing was settled between them, but wrestling fans had another favorite to add to their list. 

3. July 19, 1993: Shawn Michaels vs. Marty Jannetty

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    During Monday Night Raw's first year on the air, Marty Jannetty and Shawn Michaels battled for the Intercontinental Championship in what remains one of the best matches in the show's history.

    Michaels had been boasting in the ring about being able to beat all comers when his former tag partner challenged him to an impromptu matchup.

    Jannetty was electric, zipping in and out of the ring.  Michaels played both the cowardly heel and the favored champion.  

    The Pro Wrestling Illustrated Match of the Year was the highlight of Jannetty's career and yet another classic on Michaels' resume. 

    The fast-paced action, excellent chemistry and the surprising title change helped establish Monday Night Raw as a place for great, unmissable wrestling.  

2. May 21, 2001: Chris Benoit and Chris Jericho vs. Steve Austin and Triple H

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    The guts it took for Triple H to not only finish a match with a torn quad, but to take the Walls of Jericho is unbelievable.  His in-ring injury unfortunately often overshadows this great match. 

    There have rarely been so passionate an audience and so supercharged a match. 

    It had all the classic tenets of a tag team match yet done by such powerhouses, everything felt novel and exhilarating.  Even though the tension began at an intense level, it still managed to swell until the climax. 

    As Jim Ross nearly lost his voice, the momentum swinging back and forth, fans witnessed one of the finest tag-team matches in WWE history.

1. April 23, 2007: John Cena vs. Shawn Michaels

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    John Cena and Shawn Michaels somehow followed up their WrestleMania 23 classic with an even better match.  This showdown with a pay-per-view feel is the ultimate evidence to show to anti-Cena fans.

    It is indisputable proof that he can not only hang with a legend, but be an vital part of a near-perfect match.   

    Their battle began with a lot of mat wrestling, starting at a slow pace, but building to an exciting finish. 

    Michaels was set to get a WWE Championship shot at Backlash (albeit in a Fatal 4-Way) but this match was about pride.  It was about taking each other to the limit.

    The strain on their face, clotheslines clanging against jaws and two-counts quickening hearts all made for one of WWE's best matches and the greatest match we've seen on Raw so far. 

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