Shawn Michaels' 10 Best WWE Matches Of All Time

Sid Pullar III | Oct 24, 2024

WWE.com

Shawn Michaels has accomplished so much in his pro wrestling career. From four reigns as a world champion to the WWE Hall of Fame, "The Heartbreak Kid" has a resume that any wrestler would be jealous of. However, his legacy has been built on being one of the all-time greats inside the squared circle. Michaels has delivered time in, time out to bring in-ring excellence at its highest level. Whether it be on pay-per-view or television, there might not be another competitor with the catalog of HBK. Here are Shawn Michaels' 10 best WWE matches of all time.

10. Shawn Michaels vs. John Cena - WWE Raw 4/23/2007

In 2007, John Cena wasn't known for his ability to have a long, drawn out pro wrestling match. Despite this, Cena was unquestionably the face of WWE and had star power unlike anyone else in the business. Shawn Michaels helped Cena to one of his best bouts at WrestleMania 23, but came up short in his bid to win the WWE Championship.

On the April 23, 2007 episode of WWE Raw, the two men battled in a non-title WrestleMania rematch. They somehow were able to top their effort on The Show of Shows and left a mark on a sold out crowd in London that hasn't been forgotten to this day. Over the course of 56 minutes, Michaels and Cena had a thriller that had fans on the edge of their seats. On this night, HBK pulled out the win, but Cena may have gained more and showcased that he could go toe-to-toe with one of the best ever.

9. Shawn Michaels vs. The Undertaker (Career vs. Streak) - WWE WrestleMania 26

After failing to end his daunting undefeated streak at WrestleMania 25, Shawn Michaels became obsessed with The Undertaker and badly wanted a rematch the following year. This led to Michaels costing Taker the World Heavyweight Title and putting his career on the line for one more opportunity.

WrestleMania 26 was the stage for one of the most high stakes main events of all time. With HBK's career and Taker's streak on the line, the two legends did battle in a phenomenal bout that showcased just what both men were willing to risk to earn a win over the other. With lofty expectations after their all timer the year prior, no fan left disappointed with either competitor's effort. However, Taker put an end to Shawn Michaels in an exceptional match that capped his legendary career.

8. Shawn Michaels vs. Mankind - WWE In Your House: Mind Games

WWE

Shawn Michaels was known for giving many stars the best matches of their career. Whether it be in-ring technicians or intimidating giants, "The Heartbreak Kid" knew what to bring to the table to make any match reach new heights. At In Your House: Mind Games, Mankind received his first shot at the WWE Championship against Michaels and brought out a new side in HBK.

This might be Shawn's most physically intense war of his entire career. From big table spots to hard hitting action, this bout had it all and showed that Michaels could brawl like the Hardcore Legend. Mankind's physicality is unquestioned, but in 1996, Shawn was looked at as a clean cut, white meat babyface who needed this kind of battle to prove himself. Despite the disqualification finish, Mick Foley has often mentioned this as his favorite WWE match of his entire career.

7. Shawn Michaels vs. Triple H vs. Chris Benoit - WWE WrestleMania 20

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Triple Threat matches can often follow a formula that makes it predictable or doesn't explore the storytelling possibilities that are available with three men in the ring at once, but Shawn Michaels, Triple H and Chris Benoit bucked that trend at WrestleMania 20. This was a main event that had all three men coming in with individual journeys that came into one and delivered one of the best three-way bouts in wrestling history.

For over 24 minutes, Michaels, Triple H and Benoit battered one another, told a great story and had the Madison Square Garden crowd at a frenzy by the end. On this evening, Benoit's near-20 year odyssey was fulfilled with winning the World Heavyweight Championship and making Triple H tap out. This is not a match that will be featured in the highlight reels due to Benoit's unforgiven actions in 2007, but the performances of Michaels and Triple H are undeniable here.

6. Shawn Michaels vs. Triple H (Unsanctioned Match) - WWE SummerSlam 2002

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Speaking of the fantastic chemistry of Shawn Michaels and Triple H, SummerSlam 2002 displayed why many fans consider the DX members to be each other's greatest rivals. After four years out of the ring, "The Game" goaded his best friend back into the squared circle after viciously attacking him not once, but twice. This led to an Unsanctioned Match being made for the summer spectacle.

Using ladders, chairs and sledgehammers, Michaels and Triple H delivered a deeply captivating battle that had a hellbent energy only elevated by the Long Island crowd in attendance. For a competitor who missed four years of in-ring action, HBK didn't miss a beat and proved that he still had it. With "The Cerebral Assassin" at the top of his game, it was Michaels who pulled out a win on this night which led to him making a full time comeback later that same year.

5. Shawn Michaels vs. Chris Jericho (Ladder Match) - WWE No Mercy 2008

While Triple H went to dastardly means to goad Shawn Michaels back in the ring, Chris Jericho took things to sinister levels and mentally broke down Shawn Michaels. From bloodying the legend and punching his wife in the face, Jericho's turn to the dark side was some of the most enthralling WWE TV of that decade and offered fans a memorable feud with "The Showstopper."

Their feud culminated in HBK's signature bout at No Mercy 2008. In one of the most brutal and violent ladder matches of all time, Michaels and Jericho put each other in unimaginable pain for over 22 minutes. The aggression and intensity was off the charts. This felt like a seesaw battle that could go either way and with an inventive finish, Jericho came out victorious to retain the World Heavyweight Title to cap 2008's best rivalry.

4. Shawn Michaels vs. Razor Ramon (Ladder Match) - WWE WrestleMania X

From his last Ladder Match to the most famous one of his career, Shawn Michaels competed in the innovative stipulation on several occasions, but his WrestleMania X showdown with Razor Ramon still lives on in the minds of fans. To determine the undisputed Intercontinental Champion, Ramon and Michaels put their bodies on the line on the Grandest Stage of Them All.

Michaels became well-known for this match type, using the ladder to inflict damage on his opponent and show all the imaginative ways a wrestler could capture fans and pull them into the action. From slamming the ladder onto Razor or flying off the top from 10-feet high, Shawn stole the show and delivered the bout that put the stipulation on the map. The Ladder Match wouldn't be one of wrestling's most prominent match types without the performances of Shawn Michaels and Razor Ramon on this night.

3. Shawn Michaels vs. Kurt Angle - WWE WrestleMania 21

WrestleMania is known for dream matches that have lived up to the hype, but no showdown might have done that more than Shawn Michaels vs. Kurt Angle. This was a battle of two of the greatest wrestlers of all time trying to prove who was truly the best on the biggest stage.

Many fans had high expectations for this WrestleMania 21 match, but Michaels and Angle somehow exceeded them in this 27-minute instant classic. HBK went hold-for-hold with an Olympic Gold Medalist, while Angle displayed unbelievable character work that showed his pride being tested. The false finishes in this bout should be studied by the stars of today because it maximized every ounce of energy from the fans in Los Angeles at the Staples Center. The drama was brilliant here and felt like the end of a rollercoaster ride when Michaels finally tapped out to Angle's ankle lock to end this belter.

2. Shawn Michaels vs. The Undertaker (Hell In A Cell) - WWE In Your House: Badd Blood 1997

As mentioned before with the Razor Ramon ladder match, you would be hard-pressed to find another performer who can introduce a new stipulation quite like Shawn Michaels. However, Hell In A Cell was something that would make any competitor hesitate to take on. The steel structure would be the playground for a bloody battle regardless who was in it, but when you are locked inside the cage with The Undertaker, this is hell in every way possible.

At In Your House: Badd Blood 1997, the months-long rivalry between HBK and Taker was blown off in Hell In A Cell. After Michaels had tried escaping "The Deadman" and using D-Generation X at every chance since SummerSlam that year, he was finally trapped with nowhere to run. Over the course of 30 minutes, Taker brutalized Michaels and left him bloody in an absolutely outstanding war.

When Shawn finally was able to escape the cage, he did not get away from the fury of Taker who wound up making Michaels fall from the cage through a table. If not for the timely interference of the debuting Kane, Michaels wouldn't have survived, let alone come out victorious on this inaugural journey to hell.

1. Shawn Michaels vs. The Undertaker - WWE WrestleMania 25

With their 1997 feud a distant memory for some newer fans, Shawn Michaels and The Undertaker reigniting their rivalry was viewed as a dream match, especially on the WrestleMania stage. With a record of 16-0 going into WrestleMania 25, "The Phenom" had become the most prolific star in the event's history.

Meanwhile, Shawn Michaels had put on more classics at Mania than any other WWE star ever. From introducing premier stipulations to first time meetings, no one had upped his game on the Grandest Stage of Them All quite like Mr. WrestleMania.

At WrestleMania 25, a battle of heaven vs. hell was the starting block for one of the most sensational showdowns the event had ever seen. Taker and HBK delivered a magnificent bout that had everything you could want. The in-ring action was engrossing and gripped every fan in the Houston Astrodome. The storytelling was superb and showcased their character work on a deeply compelling level. The drama, closing stretch and finish were tremendous, and had the crowd hooked on every nearfall. On an emotional level, this is what pro wrestling is all about and has to be in the conversation for the best WWE match of all time.

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