The Best 20 Matches Of Shawn Michaels’ WWE Career
20- The Superkick Heard 'Round the World: RAW 2005 vs. Shelton Benjamin
This tremendous, fast-paced clinic against the young, athletic Benjamin took place in 2005. The highlight was Michaels reversing a springboard attempt into a perfectly timed Sweet Chin Music out of nowhere. This electrifying, shocking moment is arguably the most famous single spot in Monday Night RAW history and helped propel Benjamin's status.
19- Hardcore Heroics: In Your House 10 vs. Mankind
A critically acclaimed, often-overlooked brutal singles match. Michaels, as the WWF Champion, was put through a grueling test by the maniacal Mick Foley. The aggressive, wild brawl showcased a different side of HBK's versatility, but the phenomenal contest sadly ended in a controversial disqualification after interference from Vader and The Undertaker.
18- The One-Man Show: Royal Rumble 1995 Victory
Although not a traditional one-on-one match, Michaels made history as the first man to win the Royal Rumble from the coveted Number One entry spot. His performance, barely saving himself from elimination with one foot, was a brilliant athletic showcase and a key milestone in his career, securing his main event spot at WrestleMania by last eliminating The British Bulldog.
17- Hateful Ladder War: No Mercy 2008 vs. Chris Jericho
A brutally intense Ladder Match for the World Heavyweight Championship, driven by a deeply personal and hateful feud. Unlike earlier ladder bouts, this was a savage fight centered on aggression and injury, not aerial displays. The relentless action and hatred cemented the rivalry as a modern classic, showcasing HBK's ability to endure punishment even this late in this career.
16- Three Stages of Hell: Armageddon 2002 vs. Triple H
The final and deciding match in their initial 2002 feud, combining a Street Fight, Cage Match, and Ladder Match. This grueling, brutal marathon pushed both men to their limits. Triple H won the final stage, narrowly defeating Michaels and evening their personal score in a defining rivalry, marking their first major payoff.
15- Ladder Match Pioneer: WrestleMania X vs. Razor Ramon
This was the bout that revolutionized the Ladder match stipulation. Competing for the Undisputed Intercontinental Championship, Michaels and Ramon created an innovative, high-risk classic that set the standard for future gimmick matches. Michaels' daredevil stunts and the incredible drama of the climb made him an undeniable star and helped popularize the high-risk style.
14- The Return: SummerSlam 2002 vs. Triple H
This was Michaels' miraculous in-ring return after four years away due to a severe back injury. He faced his former best friend and betrayer, Triple H, in a violent, emotional street fight. Despite ring rust, HBK proved he hadn't lost a step, earning a cathartic victory over The Game before being brutally attacked post-match to set up their next feud.
13- The Attitude Era Launch: WrestleMania XIV vs. Stone Cold
Michaels defended the WWF Championship at WrestleMania 14 against the red-hot Stone Cold, with Mike Tyson as the Special Enforcer. Working through a severe back injury that forced his first retirement, Michaels fought through the pain before Austin won the title. This match marked the beginning of the "Attitude Era" and the end of HBK's first run.
12- The Chairman Gets His Comeuppance: WrestleMania 22 vs. Vince McMahon
This highly personal, brutal No Holds Barred match saw Shawn Michaels finally unleash years of frustration on the tyrannical Chairman. After Shane McMahon was handcuffed to the ropes, HBK decimated a bloody Vince McMahon with ladders, chairs, and a table. The dramatic climax saw Michaels execute a diving elbow drop from a massive ladder onto Vince, who was trapped in a trash can on a table, before finishing him with a decisive Sweet Chin Music.
11- Generational Clash: WrestleMania XIX vs. Chris Jericho
This match proved Michaels' 2002 comeback was permanent. The clash of eras pitted the veteran against the rising star in a masterclass of in-ring psychology. Following a brilliant, fast-paced match, Michaels scored the pin, only for a furious Jericho to deliver a low blow after appearing to offer a handshake, cementing their intense rivalry.
10- Generational Main Event: WrestleMania 23 vs. John Cena
Michaels challenged WWE Champion John Cena in the WrestleMania 23 main event, pitting the veteran "Mr. WrestleMania" against the company's biggest modern star. Despite being unwilling Tag Team Champions, the two delivered a compelling, lengthy match that focused on Michaels’ ring psychology against Cena's power. Michaels was dominant, but Cena ultimately retained the championship, forcing HBK to submit to the STF after a hard-fought contest.
9- Triple Threat History: WrestleMania XX vs. Triple H & Chris Benoit
A dramatic Triple Threat Match for the World Heavyweight Championship. Michaels' rivalry with Triple H and Benoit's quest for the title culminated in a spectacular main event. All three men delivered an emotional and technically flawless performance in a moment that was meant to crown a deserving champion in the Madison Square Garden main event. At the end, Benoit won the event and finally captured the world title after being on the road for 18 years.
8- The Cell's Debut: Badd Blood 1997 vs. The Undertaker
The inaugural Hell in a Cell match. This violent, bloody war was designed to settle the animosity between Michaels and The Undertaker. HBK was thrown around the demonic structure until the shock debut of Kane, The Undertaker's masked brother, allowed Michaels to steal the victory and retain his spot as the main event star.
7- RAW's 60-Minute Masterpiece: RAW 2007 vs. John Cena
A non-title rematch from WrestleMania 23 that lasted nearly a full hour. The two superstars delivered an exhausting, incredible performance for a non-PPV audience in London. Moreover, it led to Michaels getting even with Cena after he scored the pin with a sweet chin music while HBK fell down on Cena while performing the move. Moreover, Michaels' stamina and storytelling in this marathon match became a career highlight, proving his "Showstopper" moniker was well deserved.
6- The Heartbreak Kid's Redemption
The first-ever Elimination Chamber match took place at Survivor Series 2002. In only his second match back from a four-year retirement, Shawn Michaels defeated World Heavyweight Champion Triple H, Chris Jericho, Booker T, Kane, and Rob Van Dam. Michaels pinned his bitter rival, Triple H, with a Sweet Chin Music, capturing the championship in a shocking and emotional comeback victory at Madison Square Garden.
5- Olympic Gold Standard: WrestleMania 21 vs. Kurt Angle
This was a dream match between two undisputed technical masters of their eras. This highly anticipated encounter featured immaculate counter-wrestling, hard-hitting moves, and exceptional storytelling, with both men pulling out all their signature offense. Angle ultimately forced Michaels to submit to the Ankle Lock after a vicious, prolonged struggle, producing a 30-minute clinic in professional wrestling.
4- Boyhood Dream Achieved: WrestleMania XII vs. Bret Hart
The "boyhood dream" match for the WWF Championship lasted an unprecedented 60-minute Iron Man Match. Neither man scored a fall, forcing a sudden-death overtime. Michaels finally hit a Sweet Chin Music to secure his first world title. This dramatic, psychological marathon officially crowned HBK as the new face of the company in the New Generation era.
3- The Final Farewell: WrestleMania XXIV vs. Ric Flair
An emotionally charged, career-ending match for "The Nature Boy" Ric Flair. Michaels struggled to deliver the final Sweet Chin Music, famously whispering, "I'm sorry, I love you," before ending the legendary career of his hero and friend. The perfect, tearful farewell to a true icon in a moment of genuine respect and sportsmanship.
2- Career vs. Streak: WrestleMania 26 vs. The Undertaker
The rematch with the ultimate stakes: Michaels' career versus The Streak. Driven by an obsession to end the Streak, HBK's reckless performance forced The Undertaker to show mercy before delivering a final jumping Tombstone. It was a beautiful, emotional conclusion to one of wrestling's greatest rivalries and Michaels' full-time in-ring tenure.
1- The Greatest: WrestleMania 25 vs. The Undertaker
This is widely hailed as the greatest match in WWE history. Michaels' quest to break The Streak resulted in a breathtaking display of athleticism, drama, and near-falls that left the audience in awe. The emotional intensity from both veterans was unparalleled, with Michaels kicking out of the Tombstone and surviving The Undertaker's dive. A legendary contest that ultimately ended with a decisive, painful Tombstone taking The Deadman to 17-0.
