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Shawn Michaels is one of the best wrestlers of all time. Some fans consider him to be the best wrestler to enter a ring in WWE, but while that’s debatable, it’s clear that Michaels left a legacy in the ring that helped to tell some unforgettable stories.
The superstar managed to wow the crowd every time he entered the squared circle. A genius inside the ropes, his in-ring wrestling style along with his character work in telling his stories meant that the crowd cared about everything he did.
Over his career, Shawn Michaels has been a part of several legendary moments that no fan will be able to forget, but some of his matches stand out even among those. He was the showstopper, he was The Heartbreak Kid, he was Mr. WrestleMania – and he lived up to each of those names.
The following are twenty matches of Shawn Michaels that no fan will be able to forget.
#20 Razor Ramon vs Shawn Michaels - WrestleMania X
Shawn Michaels had a habit of making history and that’s exactly what he did against Razor Ramon at WrestleMania X.
The two opponents faced each other in the first-ever televised Ladder Match in WWE history. They pioneered the ladder match creating a type of match that has remained a favorite of fans and wrestlers around the world even today.
The two of them were facing each other to determine the real Intercontinental Champion and the feud between them was fierce. No one was sure what they were about to see in the match and Michaels and Ramon took advantage of that. They set a fast pace, hitting each other with high-risk moves.
They used the ladders for the first-ever time as weapons in a televised WWE match. The audience was in complete awe of what they were seeing as they had not expected what they would get.
Both stars put on a show in a ladder match that still holds up to this day despite the many legendary ladder matches that have taken place since then.
#19 Shawn Michaels vs Vince McMahon – WrestleMania 22
Not all of Shawn Michaels’ matches were wrestling masterpieces, but some of them were displays of how he could tell stories with anything he did in the ring.
Vince McMahon had been after Michaels for a long time, costing him opportunities and starting a feud with one of the best wrestlers in the world. He had made Michaels’ life extremely difficult for him, but at WrestleMania 22, Shawn Michaels decided to take things into his own hands. He faced Mr. McMahon in a No Holds Barred Match, which saw a lot of interference.
Shawn Michaels dealt with all of it and then handcuffed Shane McMahon to the ropes, forcing him to watch the beating he was about to deal out to his father. Michaels battered Mr. McMahon to an inch of his life and dealt with the WWE Chairman how many fans had been craving to see him dealt with.
Michaels absolutely destroyed McMahon before he put a trashcan over his boss's head and put him on top of a table. Shawn Michaels then climbed a ladder and hit a diving elbow drop from the top of a ladder and through the table. As if all that was not enough, he then hit Vince McMahon with the Sweet Chin Music to finish him.
#18 Shawn Michaels vs Shelton Benjamin - WWE RAW (May 2, 2005)
Shawn Michaels, during his second run, did a lot to help elevate a number of superstars to another tier in WWE. One such wrestler was Shelton Benjamin.
In 2005, Batista was the World Heavyweight Champion when Eric Bischoff announced that a Gold Rush tournament would be held to decide his next challenger. At this point, anyone could be facing anyone.
However, one of the matches that took the show by storm was when Shawn Michaels and Shelton Benjamin met in the quarterfinals of the tournament. At that point in his career, Benjamin had shown flashes of potential and had some crazy matches. However, fans were yet to be convinced of his ability inside the ring.
All of that changed when he faced Shawn Michaels. The match included a moment that has gone down in history as one of the most memorable moments in WWE history. Shelton Benjamin jumped off the ropes towards Michaels, who timed a superkick absolutely perfectly to knock him out of mid-air.
While the moment was memorable, the match helped elevate Benjamin to another level as fans saw that he could handle himself in the ring with one of the best wrestlers of all time.
Benjamin would never get the push that fans wanted for him, but matches like the one with Shawn Michaels ensured that they would remember his first WWE run fondly.
#17 Shawn Michaels vs The Undertaker - Badd Blood: In Your House 1997
Shawn Michaels and The Undertaker have faced each other multiple times over the years, and almost every time they have managed to create history. At the 1997 In Your House pay-per-view, Shawn Michaels and The Undertaker battled in the first-ever Hell in a Cell match.
The devilish structure made its first-ever debut in WWE with The Undertaker dominating Michaels for most of the match. The two wrestlers battled all around the ring, fighting for every inch of ground, neither willing to give way to the other.
The match was one of the most brutal matches to take place in WWE’s history at this time. Halfway through the match, a camera person was “injured” as a result of which the cell door had to be opened. The match spilled outside the cage and the two climbed up the side of the cage. Michaels ended up hanging from the side of the cell, with The Undertaker stomping on his hands. Michaels fell from the cell through the announcement table below in an extreme spot no one expected.
As if that was not enough, when the match continued inside the ring, Paul Bearer walked out with the debuting Kane. Kane ripped the door of the cell off its hinges and hit the Tombstone Piledriver on The Undertaker. Shawn Michaels took advantage to pin The Deadman and pick up the win.
#16 The Rockers (Shawn Michaels and Marty Jannetty) vs The Orient Express – Royal Rumble 1991
Many fans may not remember that before his iconic singles career, or before being part of D-Generation X, Shawn Michaels was part of The Rockers. He was a perfect tag team wrestler when he started his career. Partnering with Marty Jannetty, the two brought a freshness to all their matches that highlighted their youth and wrestling style.
At Royal Rumble 1991, The Rockers had the best match of their tag team run when they faced The Orient Express. Shawn Michaels and Marty Jannetty were one of the most popular tag teams during this time and became the inspiration of some all-time great tag teams in later generations.
However, on this occasion, they were facing The Orient Express’s hard-hitting wrestling style. It was the perfect mixture of styles and the two teams told an excellent story through a memorable match. With Mr. Fuji at ringside for The Orient Express, Shawn Michaels helped tell a brilliant story as he interfered and let Marty Jannetty hit a Sunset Flip that allowed the pair to pick up a legendary win in front of a red-hot crowd.
#15 Shawn Michaels vs Triple H vs John Cena – Survivor 2009
Shawn Michaels and Triple H were tag team partners ahead of the match as they entered a feud against then-WWE champion John Cena. Both wrestlers were looking to win the match with anything that it took.
They were ready for anything – well almost anything. Shawn Michaels began the match with what might have been one of the greatest moments of any wrestling match as he superkicked Triple H out of the ring. John Cena stared on slack-jawed as the crowd tried to comprehend that within seconds of the match starting, Michaels had already superkicked his best friend.
Michaels would not win that match, but the show that he was able to put on with Triple H and John Cena was one of the best of all time. The three went on to have a match that John Cena won, but the superkick to start the match alone made this one of the matches that had to be mentioned in the most unforgettable of HBK’s legendary career.
#14 Shawn Michaels vs Bret Hart - WrestleMania XII
Over the years, the Iron Man Match between Shawn Michaels and Bret Hart has received a lot of criticism for being too long. The match took place for over an hour and the two wrestlers had to pace themselves to last the entire time.
The match was affected by a variety of reasons. There was not a single fall in the one hour that the two men battled and apparently, there were backstage political reasons behind this. At this time, Bret Hart and Shawn Michaels were already clashing behind the scenes and didn’t trust each other. As a result, neither man was willing to let the other get a fall over them in case they then didn’t do things according to plans.
However, the match was one of the best of all time between two of the best wrestlers of all time. As a result, despite the many external factors, the match was one of the best of all time.
When neither star was able to get a fall, there was a sudden death finish where Shawn Michaels defeated Bret Hart to win the Iron Man Match and become the WWE Champion. It was an iconic moment in Michaels’ career that is still talked about to this day.
#13 Shawn Michaels vs Diesel - In Your House 1996
Shawn Michaels managed to bring the best out of any wrestler. Kevin Nash, aka Diesel, was never the best in-ring worker in WWE. But at times, he could bring out a different side of himself, and that’s what happened at In Your House 1996. He faced Shawn Michaels at the pay-per-view in what would be one of his final matches of his WWE run.
Michaels and Diesel had a long-storied history as the two wrestlers were very familiar with each other. They had been best friends at a time but circumstances had changed that. Diesel was leaving WWE to go to WCW and he put on what might be the best match of his career against Shawn Michaels at this point.
It was the final televised match for Diesel, and he went out with a bang. They put everything into the match as they used steel chairs, fire extinguishers, and everything else they had to get the advantage. Shawn Michaels ended up winning the match with the Sweet Chin Music that allowed him to pin Diesel and retain the WWE Championship.
#12 Shawn Michaels vs Rey Mysterio – Eddie Guerrero Tribute Show
When Shawn Michaels faced Rey Mysterio in the tribute show for Eddie Guerrero, it was always bound to be an emotional match. Just one day after Eddie Guerrero’s passing, a devastated Rey Mysterio still decided to compete.
He faced a man he had never wrestled before – Shawn Michaels. Mysterio was emotional throughout and everything he was doing that night was to make his late best friend proud. He could not have chosen a better opponent. Michaels and Mysterio told a heart-breaking story that night, with some amazing action. Shawn Michaels tried submissions, there were crazy reversals, and Rey Mysterio won with a sudden 619 followed by a leg drop.
It was never a classic match for wrestling, although the wrestling was faultless. For once, the match was bigger than either of the two competitors as they paid tribute to one of the greatest wrestlers to ever enter the ring, Shawn Michaels and Rey Mysterio hugged after the match in one of the most emotional moments in WWE history.
#11 Shawn Michaels vs John Cena – RAW in the UK, 2007
Shawn Michaels was back in WWE and was friends with Triple H as a part of D-Generation X in 2007. The two wrestlers often assisted each other in their matches, but there were times that they went into their own feuds and focused on their own careers instead.
Shawn Michaels and John Cena were not supposed to have a feud. Triple H was supposed to face Cena in a rematch from their WrestleMania bout, but thanks to a quad injury, he could not be at WrestleMania. Instead, Shawn Michaels faced John Cena and the two had an extraordinary match at WrestleMania.
However, they were not satisfied with that extraordinary display and instead decided to face each other in a match that went on for almost 60 minutes on RAW. WWE continued to advertise other matches during this time but they would never happen as Michaels and Cena showcased one of the best matches of either men’s career. The match is considered to be one of the best matches to have ever taken place during a regular RAW.
#10 Shawn Michaels vs Rob Van Dam vs Triple H vs Kane vs Chris Jericho vs Booker T - Survivor Series 2002
While Shawn Michaels’ return match at SummerSlam 2002 was spectacular, his match inside the first-ever Elimination Chamber after Triple H “crippled” him again was a moment that will go down in wrestling history.
Not only was this the first time fans saw the Hellish Elimination Chamber, but it was also the first time in almost half a decade that Shawn Michaels was competing for a world championship.
Michaels entered the match as the last participant while the likes of Rob Van Dam, Triple H, Kane, Booker T, and Chris Jericho did battle before him. Bloodied and battered, the superstars put on an amazing match-up.
Shawn Michaels entered fresh at No.6, but the others ensured that fans could not talk about how he had the advantage for too long. They beat him down, and soon he was bleeding much like the rest of them.
But then came the magical moment. One by one all the other wrestlers had been eliminated. Shawn Michaels and Triple H were the last ones standing. Neither had the strength to continue for long, but they had a match within a match, as they battered each other with a hatred that had not been seen in WWE in a long while.
In the end, Shawn Michaels made history hitting Triple H with a final superkick before falling on him for the cover. He won the World Heavyweight Championship in his first official pay-per-view back, as the SummerSlam match had been “unsanctioned”.
What made the win even more iconic was that it would be Michaels’ final run with a world championship in WWE.
#9 Shawn Michaels vs Chris Jericho – Unforgiven 2008
Shawn Michaels and Chris Jericho always had incredible chemistry in the ring when they faced each other. However, their match at the 2008 WWE Unforgiven pay-per-view was a love letter to some of the best character work ever by Shawn Michaels.
The feud between the two men had turned extremely bitter. They could not stand each other. Jericho had attacked Michaels and had caused an “injury” that almost caused Shawn Michaels to retire from the ring. However, when Jericho attacked Michaels during his retirement speech and accidentally punched his wife, it was the moment that Michaels needed to stay in.
The two faced each other in an unsanctioned match that no one was ready for. Michaels overcame Jericho’s assistant at the time, Lance Cade, and battered the superstar. He put both men on the announcers’ table and hit them with a diving elbow drop.
Then Michaels did what only he could. Even though he had the advantage and was beating Jericho, he brought out all the emotion and fury he could summon. He started to cry while attacking Jericho. This was the man who had almost made him retire, who had hurt his wife. In what would have been an otherwise heel move, the audience joined Michaels in his heart-breaking fury as he demolished Jericho.
He didn’t use any special moves but simply attacked him, looking to injure him. The referee decided that Jericho could no longer wrestle and ended the match in Michaels’ favor instead. Michaels won, but he stood there with no sense of victory, a broken man who had simply been on a mission.
Even after the referee stopped him, upset and shaking with rage, he hit the referee with Sweet Chin Music, still overcome by righteous grief as fans chanted his name. A moment that only Shawn Michaels could have created.
#8 Shawn Michaels vs Kurt Angle – Vengeance 2005
Shawn Michaels and Kurt Angle faced each other for the first time at WrestleMania 21. But three months after that iconic match, the two wrestlers faced each other again.
When Kurt Angle came to RAW as part of the WWE Draft, Shawn Michaels challenged him to a WrestleMania rematch at WWE Vengeance. Angle accepted the match and they faced each other again.
By this time, the two stars were very familiar with each other. They both looked to outdo each other but they were very ready for the offense that the other wrestler brought to the ring. Kurt Angle looked to ensure he would win again, but Shawn Michaels was the one who came away with the win this time.
Michaels learned from his last loss and adapted to face Angle, eventually winning with the Sweet Chin Music. The match was one of the best that either had put on again and was the one that stole the show at the Vengeance pay-per-view.
The two would face each other in a tie-breaker Iron Man Match, but even that ended in a 2-2, leaving them tied as Kurt Angle left WWE soon after.
#7 Shawn Michaels vs Chris Jericho - WrestleMania 19
Shawn Michaels was always capable of putting on the best matches of all time. When facing Chris Jericho, the chances of the two of them putting on an all-time great match just became even more likely.
Chris Jericho was looking to prove that he was as good, if not better, than the legendary Michaels at this point in his career. He played the role of the despicable heel perfectly, helping Shawn Michaels to look like an even bigger face than he was. Jericho mocked Michaels throughout the match even trying to win with the Sweet Chin Music.
However, when Shawn Michaels hit his own Sweet Chin Music, Jericho was able to survive. The match would not last long after that. Jericho tried to hit Michaels with a suplex, but Michaels countered, rolling him up and getting the win.
What made the match even better was what happened after the two of them were done. Jericho offered to shake Michaels’ hand and it seemed they would put their issues behind them. Instead, Jericho hit Michaels with a low blow, making for an iconic WrestleMania moment.
#6 Shawn Michaels vs The Undertaker - WrestleMania XXVI
Shawn Michaels faced The Undertaker multiple times over their careers in WWE, and on each occasion, the two of them managed to produce something magical. The first time they had faced each other at WrestleMania was special in its own way, but that’s for later.
The second time they faced each other, everything was on the line.
Desperate after losing to The Undertaker a year back, Michaels tried to work his way into a match by attempting to win the Royal Rumble. When that failed, Shawn Michaels ensured The Undertaker was not the World Heavyweight Champion during WrestleMania. He interfered in the Elimination Chamber and helped his arch-nemesis Chris Jericho win the match just so that The Phenom would accept his challenge.
The Undertaker accepted Michaels’ challenge, but it came at a cost. Shawn Michaels’ career was on the line against The Deadman’s Streak.
The match was everything that it could have been. Learning from their experiences a year ago, both wrestlers tried to avoid mistakes they had made then. It was entertaining for the fans and the quiet desperation with which Michaels approached the match made fans believe that The Undertaker’s streak was in danger.
However, by the end of the match, it was The Undertaker who stood tall, and the career of one of the best wrestlers of all time was at an end. Shawn Michaels lost to The Undertaker and had to retire from the ring.
#5 Shawn Michaels vs Triple H - SummerSlam 2002
Shawn Michaels' return to WWE in 2002 was one of the most iconic moments in the company's history. For four years, it had appeared that Michaels had stepped inside the ring to compete for the final time.
Thanks to a crippling injury four years back, his in-ring career had seemingly come to an end. However, at SummerSlam 2002, Shawn Michaels returned to the ring after a betrayal by his best friend – Triple H. The match was unsanctioned and fans didn’t expect much from it. They thought that it would be a typical brawl.
The Shawn Michaels that appeared at the event, made them all rethink their idea of his condition. At no point did it look like Michaels had not wrestled for the better part of four years. He had re-entered the ring as if he had never left and the match was one of the best that had been seen in years.
He returned to the ring and started to jump off ladders immediately after what was thought to be a critical injury. The match is one of the best of all time when talking about his many appearances in the ring thanks to the shock factor attached to it, as well as his innate ability to draw in a crowd.
Shawn Michaels’ return to the ring in 2002 was the start of what would be a much better run in WWE than his own legendary original WWE run.
#4 Shawn Michaels vs Kurt Angle – WrestleMania 21
Shawn Michaels and Kurt Angle are two of the best wrestler to have ever entered a WWE ring. Despite the differences in their wrestling styles, when they entered the ring, it was always going to be a classic match.
The two started to feud after Shawn Michaels eliminated Kurt Angle from the 2005 Royal Rumble match and they then started to wrestle each other. Kurt Angle was furious about the elimination and appeared to devote his life to mocking Shawn Michaels. This was also the time when the iconic song by Angle mocking Michaels’ theme came about. Angle worked alongside Sensational Sherri, promising to hurt ankles.
The feud could have been brilliant, but the match delivered on all cylinders at WrestleMania 21. The two told a brilliant story and Kurt Angle won the match where he made Shawn Michaels tap out with an extreme ankle lock. The match was one of the best in WrestleMania history and in both men’s careers as well. The crowd gave Michaels a standing ovation after the match in another iconic moment in his career.
#3 Shawn Michaels vs Ric Flair - WrestleMania XXIV
Ric Flair’s retirement match against Shawn Michaels remains one of the best farewell matches of any legendary wrestler.
By the time WrestleMania XXIV rolled along, Flair had aged and could no longer wrestle in the ring as he had before. He was a shadow of his former self and any fan could see that it was time for him to bid farewell to his in-ring career.
Shawn Michaels faced Ric Flair in a match where if Flair lost, he would have to retire once and for all. The Nature Boy didn’t make it easy for Michaels.
He pulled out every trick in the book, hitting him with every move that he had made famous over his legendary career in the ring. Michaels, to his credit, played up each moment for everything that it was worth.
He hesitated at all the right moments as it looked like he could not bring himself to be the one to end Ric Flair’s career. Then came the moment. Shawn Michaels hesitated, getting ready with the final Sweet Chin Music. Flair begged him on and Michaels mouthed, “I’m sorry. I love you.” Then he hit Flair with the Sweet Chin Music. He fell on the legend and pinned him. Just like that, Flair’s career was over.
After the match, Michaels hugged Flair for a brief moment, before leaving the ring, not bothering to celebrate, giving Ric Flair the moment with the fans he deserved.
#2 Shawn Michaels vs Triple H vs Chris Benoit – WrestleMania XX
Triple Threat matches have the potential to be some of the most exciting bouts that an audience has ever seen, and Shawn Michaels has been a part of several of them.
At WrestleMania XX, it was all about Chris Benoit, more so than Triple H or Shawn Michaels. Far removed from the future that no one could have imagined, the event was Benoit’s crowning moment after years of struggling to break out as a main event performer. He was a wrestler who fans loved at this point in his career.
The desperation in the match was clear as there were several stories being told. Shawn Michaels and Triple H had a bitter rivalry that could never be put to the side. At the same time, Chris Benoit was finally getting that WrestleMania moment that he had been working for his entire career. All three men were pictures of desperation as they all participated in a match in which they felt they had no other option but to win.
The match was incredible, hard-hitting, and exciting with near-falls the way only a Triple Threat match can be. However, it was the story of Chris Benoit, long before his tragic and despicable actions that would cast a shadow over his entire life. Chris Benoit won and his celebration with Eddie Guerrero after that would be a moment that very few wrestling fans could watch without a tear in their eyes.
#1 Shawn Michaels vs The Undertaker - WrestleMania XXV
The first time Shawn Michaels met The Undertaker at WrestleMania may perhaps be the best match of all time. While fans will always argue about which is the best wrestling bout, when Michaels faced The Deadman, they created a match that would be the best of either of their careers.
Shawn Michaels was looking to end The Undertaker’s streak and had left nothing behind in his quest to mock the legend and provoke him leading into their match.
They threw everything they had with each other. The Undertaker took massive bumps, flying over the top rope to the outside, where a prop-camera person failed to catch him and he landed head-first on the ground. Michaels dove to the outside hurting himself. Both wrestlers worked like it was the one match of their career that they would be remembered for, not giving ground, and with near-falls that left the other in disbelief.
Finally, there came a time when Shawn Michaels made the wrong move, and The Undertaker caught him, delivering the Tombstone Piledriver that brought an end to proceedings. The match saw the rest of the pay-per-view fade into the background as Michaels and ‘Taker delivered a classic that should have been the main event of the night.
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