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Top 50 Shawn Michaels Rivalries

WWE Hall of Famer Shawn Michaels was once ranked as The Top WWE Superstar Of All Time by his peers, and there's little reason as to why. He's a four-time World Champion and has been nicknamed Mr. WrestleMania for his show-stopping performances at the annual event. And even outside of WWE's reach, Pro Wrestling Illustrated magazine readers nominated him for Match of the Year honors an unprecedented 11 times during his career. Of course, Michaels wouldn't have had the career he did without a steady stream of opponents to match up against. 

In counting the Top 50 Shawn Michaels Rivalries, Wrestling Merchandise and Memories looked at the following criteria:


  • How prominent was the rivarly?

  • What type of stage(s) did it play out on?

  • How memorable were the matches and/or segments?

  • How much did the rivalry do to advance either person's career?


If you'd like to be a part of this conversation, Tweet us at @canadianbulldog using the hashtag #Top50, or leave a comment below.


Ready? Here we go!


Randy Savage

WWE Hall of Famer Randy Savage apparently wanted to have a two-year program with Shawn Michaels that would end with the Macho Man passing the torch to The Heartbreak Kid That never happened, but Michaels was challenged by Savage for his Intercontinental Title in 1992.


Tito Santana

WWE Hall of Famer Tito Santana faced Shawn Michaels in the opening match at WrestleMania VIII, a few short months after Michaels turned heel. While HBK got the win, the two faced each other on house shows and even on WWF's syndicated television shows.


The Big Show

The Big Show and Shawn Michaels managed to meet, primarily in several high-profile tag team encounters. Most notably, Michaels and Triple H battled Big Show and Chris Jericho, while D-Generation X battled Show and The McMahons at 2006's Unforgiven PPV.


Chris Masters

In 2005, Chris Masters was tormenting fan favorites with his Masterlock Challenge. When Shawn Michaels wouldn't give in to the hold, Masters blasted him with a steel chair instead. This led to a brief program that included a one-on-one match at that year's Unforgiven PPV, which Michaels won.


Ted DiBiase

WWE Hall of Famer Ted DiBiase battled Shawn Michaels in the early 1980s in the Mid-South territory. Michaels later said that he was a jobber at the time, and the future Million Dollar Man was the first person to let him have a decent match at the time. They also clashed in the WWF.



Crush was seen by many fans as the man to defeat Shawn Michaels for his Intercontinental Title when the two met at King of the Ring in 1993. However, Michaels had a couple of things going for him - his new bodyguard Diesel, and a pair of cigar-smoking Doink The Clowns - which gave HBK the win.


Jim Cornette

During the first WWF World Title reign of Shawn Michaels, the manager who most persistently chased him was Jim Cornette. Cornette sent Vader, Davey Boy Smith and Owen Hart after HBK. He even ended up doing battle with Michaels's manager at the time, Jose Lothario, in a match featured on pay-per-view.


Shelton Benjamin

Shawn Michaels and Shelton Benjamin had but one match in their respective careers, but it was a doozy. As part of the "Gold Rush" tournament held on Raw in May 2005, the two had a series of nearfalls and reversals that made for an all-time classic for Raw, with Michaels barely squeaking out a victory.


Ken Shamrock

In late-1997, Ken Shamrock emerged as the number one contender to Shawn Michaels's WWF World Title. HBK boasted that he wouldn't tap out to Shamrock's ankle lock, and avoided it in his first title defense at the pay-per-view In Your House: D-Generation X


The Legacy

In 2009, The Legacy (Cody Rhodes and Ted DiBiase Jr.) battled D-Generation X (Shawn Michaels and Triple H) on three consecutive pay-per-views: SummerSlam, Breaking Point and Hell In A Cell. While The Legacy won the middle match, DX were victorious in the first and third challenges.


Shane McMahon

During the lead up to their match at WrestleMania XXII, Vince McMahon sent his son Shane McMahon after Michaels to soften him up. Shane and Shawn battled in a Street Fight on Saturday Night's Main Event, which Shane O'Mac actually won due to a screwjob finish, and the two later clashed in various tag matches.


The Spirit Squad

Without The Spirit Squad, it's possible that Shawn Michaels would have never reunited with Triple H in D-Generation X in 2006. Egged on by Vince McMahon, the faction of Kenny, Johnny, Nicky, Mikey and Mitch took on Michaels and The Game in a series of tag team matches on television, at live events and on PPV.


Arn Anderson & Tully Blanchard

One of the toughest challenges The Rockers ever had was from WWE Hall of Famers Arn Anderson and Tully Blanchard, a/k/a The Brain Busters. The two teams battled twice on Saturday Night's Main Event, not to mention at the Survivor Series in 1989 and all over the house show circuit. 



In the months leading up to WrestleMania IX, the then-undefeated Tatanka managed to pin Shawn Michaels in a handful of tag team and non-title matches. Then they clashed at WrestleMania, with Sensational Sherri in Tatanka's corner and Luna Vachon in Michaels', with Tatanka winning the match by countout.



Upon his 1996 arrival in the WWF, Vader set out on a path of destruction until he was granted a match against WWF World Champion Shawn Michaels. The two battled at SummerSlam, and Vader took HBK to the limit, but ultimately received his first WWF loss at the hands of Michaels.


Kurt Angle

In something of a dream match situation, WWE Hall of Famer Kurt Angle had Shawn Michaels had a series of matches in the mid-2000s. They first battled at WrestleMania XXI, with Angle getting the win. The next clash was at Vengeance a year later, which HBK won. The rubber match - an Iron Man match on Raw - ended in a tie.


John Bradshaw Layfield

John Bradshaw Layfield's rivalry with Shawn Michaels was unlike any other before or after it. Facing financial problems, Michaels struck a deal with JBL to receive enough money to clear his debts. However, this meant Michaels had to act as JBL's lackey until The Heartbreak Kid had enough and fought back.


Randy Orton

Randy Orton and Shawn Michaels collided several times over the years, with the first major match being at Unforgiven in 2003. Michaels also returned from a hiatus in late-2007 to challenge Orton for his WWE Championship at that year's Survivor Series, when The Legend Killer hit an RKO out of nowhere.


Owen Hart

Shortly after Shawn Michaels was injured in real life, he battled Owen Hart on Monday Night Raw. The match ended prematurely when Michaels appeared to pass out as the result of a concussion, giving The King Of Harts a psychological advantage. They feuded again in early 1998 after Owen's brother Bret left the WWF for WCW.


Hulk Hogan

In early 2005, WWE Hall of Famer Hulk Hogan returned, and Michaels recruited him to take on Muhammad Hassan and Daivari. After a win on Monday Night Raw, Michaels superkicked Hogan and turned heel for the first time in many years. The two battled at that year's SummerSlam, with Hogan coming out on top.


Sycho Sid

In 1995, Shawn Michaels was determined to wrest the WWF World Title from his former friend Diesel, and hired Sycho Sid as a bodyguard. When HBK failed at that year's WrestleMania, Sid turned on him and a new rivalry was born. It was ignited again in 1996, when the two traded the WWF World Heavyweight Title back and forth.


Stone Cold Steve Austin

Although they had once been WWF Tag Team Champions together (briefly),  WWE Hall of Famer Stone Cold Steve Austin and Shawn Michaels never quite saw eye to eye. Never was this more apparent than in the lead up to their WrestleMania XIV main event. Austin won their match (and the WWF World Title), marking Michaels' last match in the company for years.


Marty Jannetty

"Is there a problem between The Rockers? I don't think so!" Shawn Michaels spat, seconds after he threw former partner Marty Jannetty through the window of The Barber Shop talk show set. Thus ended a seven year-long partnership between The Rockers in the AWA and WWF and ignited a feud between the two in early 1992. Jannetty soon left the WWF, but returned a year later to capture the Intercontinental Title from Michaels.


Razor Ramon

When Michaels was suspended by the WWF in 1993, he was stripped of his Intercontinental Title. A short time later, WWE Hall of Famer Razor Ramon was named Michaels's successor for the title.. which was fine until Michaels returned to the company with his own version of the belt. The two had a classic ladder match at WrestleMania X, won by Ramon, and another ladder match at SummerSlam a year later, which HBK won.


Triple H

While most people think of WWE Hall of Famer Triple H and Shawn Michaels as partners in D-Generation X, they have spilled their fair share of bad blood as well. When Michaels returned to the WWE in 2002, The Game turned on him, resulting in HBK's first match back at that year's SummerSlam. The two had an on-again, off-again rivalry for the better part of two years.


Sgt. Slaughter

WWE Hall of Famer Sgt. Slaughter had a memorable rivalry with Shawn Michaels while Slaughter was WWF Commissioner and Michaels was part of the original D-Generation X. The Showstopper (along with Triple H and Chyna) made fun of Slaughter's chin, voice and penchant for spitting before Sarge fought back.


Bob Backlund

When Bob Backlund unexpectedly returned to the WWF in 1992, one of his first opponents was Shawn Michaels, whom the former WWWF World Champion handily defeated.  Later, when Backlund challenged Diesel for the WWF Championship, Michaels was his advisor.


Jeff Jarrett

Shawn Michaels and WWE Hall of Famer Jeff Jarrett battled for Double J's Intercontinental Title at the second In Your House PPV in 1995. The two also locked horns a couple of years earlier, when Michaels was on loan from the WWF and Jarrett was in the USWA.



Though Batista and Shawn Michaels first did battle at Armageddon in 2003, they later had a more nuanced feud when both were fan favorites. In 2008, after Michaels had retired Batista's best friend Ric Flair, The Animal was out for blood. The two did battle in a Stretcher Match at One Night Stand, which Batista won.


The 123 Kid

While Shawn Michaels and WWE Hall of Famer The 1-2-3 Kid (Sean Waltman) were part of The Kliq, they battled in 1993 in both singles and tag team matches featuring Diesel and Razor Ramon. They also fought on Monday Night Raw in a high-profile match.


Mr. Kennedy

Shawn Michaels and Mr. Kennedy began doing battle in late-2007, with a first match that ended in a no-contest. This led to a one-on-one bout at Armageddon, which Michaels won, and a rematch on Raw, won by Kennedy. The rubber match took place on January 21, 2008, and was won by The Heartbreak Kid.


Sensational Sherri

WWE Hall of Famer Sensational Sherri and Shawn Michaels were first on opposite sides in 1986, when The Midnight Rockers challenged Buddy Rose and Doug Somers in the AWA. Later, Sherri came to the WWF as Michaels's manager, but once they split in 1993, Sherri vowed to get revenge on HBK.


Power & Glory

One of the last big rivalries Michaels and Marty Jannetty (The Rockers) had as a tag team was against Power & Glory, the Slick-managed tag team of Paul Roma and Hercules. Power and Glory turned on The Rockers, in fact, and injured the knee of Michaels, giving them the victory at SummerSlam 1990.



Christian clashed with Shawn Michaels numerous times on television, including a series of matches on Raw in 2004 as well as the house show circuit. While Captain Charisma never quite got the upper hand, he did aid Chris Jericho in Y2J's ongoing rivalry with The Heartbreak Kid.



Kane fought Shawn Michaels a number of times during the brand split era of Monday Night Raw, stemming from the fact that The Big Red Machine was jealous of HBK competing for the World Title. The two squared off in a No Disqualification Match at Unforgiven in 2004, which Michaels won.


Mr. Perfect

WWE Hall of Famer Mr. Perfect's rivalry with Shawn Michaels began in 1993, and included a memorable parking lot brawl on Monday Night Raw. This led to a match at SummerSlam of that year for Michaels's Intercontinental Champion, which HBK managed to win by countout, adding even more fuel to the fire.


Chris Benoit

When Chris Benoit won the Royal Rumble in 2004, he was set to challenge Triple H at WrestleMania XX but Shawn Michaels stepped in. This led to a classic pair of Triple Threat matches at WrestleMania and Backlash, while Michaels challenged Benoit one-on-one on Raw that year, though he never won the belt.



Furious that fans voted for Shawn Michaels at the inaugural Taboo Tuesday instead of him, WWE Hall of Famer Edge turned heel and made HBK his first victim. The two clashed at the Royal Rumble in 2005, and they feuded again as part of the D-Generation vs. Rated RKO rivalry that culminated in a match at New Year's Revolution.


Rick Martel

Rick Martel had an interesting feud with Shawn Michaels in the summer of 1992. Both were heels at the time and were competing for the affections of Michaels's manager Sensational Sherri. This resulted in a match at SummerSlam in which all punches to their model-like faces were banned.



Just one month after Shawn Michaels turned back the challenge of Vader, he began a rivalry with WWE Hall of Famer Mankind (Mick Foley), with a match at In Your House: Mind Games from Philadelphia. Michaels barely won the match, and the two crossed paths again about a year later.


Doug Somers and Buddy Rose

When Shawn Michaels and Marty Jannetty were The Midnight Rockers in the AWA, they were quickly paired up against the team of Doug Somers and "Playboy" Buddy Rose. The Rockers chased them for well over a year before finally beating them to capture the AWA Tag Team Titles in January 1987.


The Fabulous Rougeau Brothers

The Fabulous Rougeau Brothers (Jacques and Raymond Rougeau) had a feud with The Rockers in 1989 when The Rougeaus attacked Shawn Michaels in the throat with Jimmy Hart's megaphone. The teams had a series of marathon matches, and in a six-man tag match at SummerSlam.


The British Bulldog

Shawn Michaels's first championship belt came at the hands of The British Bulldog (no relation) in 1992 when he captured the Intercontinental Championship. The two battled at the Royal Rumble 1995 (where Michaels and Smith entered as #1 and #2, respectively) and even over the European Championship.


John Cena

John Cena and Shawn Michaels were World Tag Team Champions in early 2007 when Michaels won a number one contenders match to challenge Cena in the main event of WrestleMania XXIII. Their friendship - shaky to begin with - quickly deteriorated as HBK focused on regaining the WWE Championship. Michaels failed in his WrestleMania bid.


Ric Flair

The first match between Shawn Michaels and WWE Hall of Famer Ric Flair was in 1992 when Michaels was still one half of The Rockers. They feuded later when Flair was part of Evolution, and had a classic match at WrestleMania XXIV, in which Flair was forced to retire after losing his match to the aptly-named Mr. WrestleMania.


Vince McMahon

Vince McMahon wasn't happy that Shawn Michaels changed his ways when returning to WWE in 2002 and hated that HBK had gotten over the events of the Montreal Screwjob. McMahon goaded him into a match at WrestleMania XXII. And when D-Generation X reformed in 2006, it was solely created with the intent of making McMahon's life more difficult.



Shawn Michaels brought WWE Hall of Famer Diesel (Kevin Nash) into the WWF in 1993. Soon, the duo dominated the WWF's Intercontinental and Tag Team Championships, but by the Survivor Series in 1994, Diesel abandoned Michaels and turned face. This ignited a feud between the two that culminated in a match at WrestleMania XXI, and another feud that began in early 1996.


Chris Jericho

Two of Shawn Michaels's biggest programs were at the hands of Chris Jericho, a man who patterned his career after The Heartbreak Kid. The first led to a classic match at WrestleMania XIX, in which the two appeared to embrace, only to have Michaels receive a low-blow from Jericho. Some five years later, Jericho would turn on Michaels again during his Highlight Reel talk show, leading to an epic series of matches between the two.


The Undertaker

The Undertaker was another instance where Shawn Michaels had not but two epic programs. The first one began in mid-1997, when Michaels cost The Dead Man his WWF World Title. The two battled in the very first Hell In A Cell match. Things cooled down for more than a decade, when Michaels attempted to end Undertaker's WrestleMania streak in 2008 and again in 2009, the latter of which cost Michaels his wrestling career.


Bret Hart

Shawn Michaels and WWE Hall of Famer Bret Hart have a storied history. The two first battled as members of The Rockers and The Hart Foundation, respectively. When Michaels was Intercontinental Champion in 1992, he challenged World Champion Bret Hart at that year's Survivor Series. At WrestleMania XII, Michaels defeated Hart for his first WWF World Championship. And of course, there was the Montreal Screwjob in 1997, in which Michaels's tainted victory over Hart played off of years of the rivalry.

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