When I put out that I was putting this list together in my Discord and on my Instagram page asking for match recommendations to watch back to make sure I wouldn’t miss anything, this match came up a lot. As someone who isn’t the biggest John Cena fan (especially in 2007), I would have loved to have kept this off my list of Shawn Michaels’ best matches. That being said, putting my personal opinions aside and looking back with rose-tinted glasses, I’d lose some credibility for not including this match. To be honest, I remember watching it live when it aired (rooting for HBK, of course!) and being impressed with the match as a whole. It took place in front of a hot United Kingdom crowd. It had great storytelling, kept a great pace for a match that went an hour, and it was one of the best matches of 2007. That all being said, it does feel too long watching it back now although it’s still very good. Also, with the matches we’re spoiled with today, I can see younger fans getting bored with this one.

This all started when Shawn defeated Ric Flair at WrestleMania XXIV, forcing Ric Flair to retire. Flair was a mentor to Batista, so of course it didn’t sit well with him. Batista believed Shawn wanted to retire Flair selfishly to cater to his own ego. This was a rematch of their first encounter from Backlash 2008 where Chris Jericho was the special referee. Shawn faked an injury to get the win there, which didn’t sit well with both Batista and Jericho. It further backed up Batista’s negative sentiment about HBK and made Jericho question his faith in the man himself. It really felt like Shawn and Batista actually hated each other during this brutal matchup. They worked the stretcher gimmick perfectly and in the end, Batista defeated Michaels. It showcased the obvious – that Shawn’s selling has always been top-tier. I just had to put this one on my list of Shawn Michaels’ best matches!

Shawn and “The British Bulldog” Davey Boy Smith have always had great chemistry, in my opinion. HBK and Davey Boy were both super agile, but Bulldog was more of the powerhouse whereas HBK utilized far more finesse. I went back and watched all of their matches again before writing this article as I did for the other matches on this list. It really came down to their match at One Night Only 1997 and this match at King of the Ring 1996. Although I find their One Night Only match memorable, it was more for the hot UK crowd and the unexpected result of Shawn winning the WWF European Championship. It was also when Shawn was the most arrogant and THE rivalry with the Hart family bled into real life.

However, their match at King of the Ring ’96 (as a pure wrestling match) is just technically better. It starts off slow and technical but picks up to be more of a competitive brawl. Mr. Perfect was the special enforcer, Owen Hart was on commentary, Jim Cornette was in Davey Boy’s corner, and Jose Lothario backed up HBK’s. All those factors added an extra sense of drama and intrigue to the match as a whole. Shawn retained his title and a brawl ensued with Camp Cornette soon after that also featured Ahmed Johnson and The Ultimate Warrior. All those factors add up to produce another one of the Shawn Michaels’ best matches of all time.

This is one of those hidden gem matches that most fans might forget because it took place on an episode of Monday Night Raw rather than at a big PPV event. Edge and Shawn had been feuding for months as Edge was starting to gun for the top of the card. They had their first match at the 2005 Royal Rumble. They would face each other again a week after Edge viciously attacked Shawn backstage. The Street Fight stipulation got attached to their next encounter – this means come as you are and there would be no rules to worry about.

Both men came out in jeans and your everyday streetwear. This was a dramatic match where Shawn ended up fighting from underneath against the most violent version of the “Rated R Superstar.” Shawn got brutally busted open, which added a lot to the match as the commentators kept putting over how much blood Shawn was losing. Both men got ladders and chairs involved in this heated brawl, too! In the end, Edge’s overconfidence and obsession to win cost him the match when HBK landed a Sweet Chin Music out of nowhere for the win. This hardcore grudge match deserves plenty of love on my list of Shawn Michaels’ best matches.

Around the time of this multi-man war, Shawn had been feuding with Edge and Randy Orton, going back to the back end of 2006. He went on to defeat both Orton and Edge in a Triple Threat Match to earn a shot at Cena for the WWE Championship at WrestleMania 23. Sadly, Shawn was unsuccessful in defeating Cena for the biggest prize in the company on the biggest stage of ’em all. Following ‘Mania 23, Orton and Edge re-entered the title picture. This led to a Fatal-Four Way clash between Edge, Orton, Michaels, and Cena for the WWE Championship. This was a fast-paced match that showed no signs of slowing down as it went down. Each guy had moments where it seemed like they were going to win. But in the end, an exhausted HBK planted Cena with some Sweet Chin Music who shockingly landed on Orton to grab the pinfall victory.

WWE’s longstanding narrative is that Razor Ramon vs. HBK at WrestleMania X for the WWF Intercontinental Championship was the first-ever ladder match in WWE history. However, this is historically incorrect – there is a crucial piece of match footage that WWE has released to prove that last statement as fact. In his autobiography, Bret talks about how he originally pitched the Ladder Match idea to Vince McMahon since it was something his father’s promotion did back in Stampede Wrestling.

Two years before Vince marked the grand debut of the Ladder Match stipulation under the bright lights of WrestleMania, he tested it out with HBK and “The Hitman.” Sensational Sherri was in Shawn’s corner, which stacked the odds in his favor. Bret and Shawn always worked so well together, even when they weren’t getting along in real life so that says a lot. This pick’s a good look at the early stages of the Ladder Match layout that deserves mentioning among Shawn Michaels’ best matches, so seek it out if you’ve never seen it.

Sycho Sid and HBK had a lot of history up until this match transpired. At one point, Sid became Shawn’s new bodyguard while HBK was feuding with Diesel in 1995. Earlier in the summer, when Shawn and Ahmed Johnson needed a replacement for The Ultimate Warrior to team with them against Camp Cornette, they re-introduced Sid as their partner. Soon after, Sid became the number one contender to face HBK after beating Vader at WWF In Your House 11: Buried Alive.

Both men came to blows at the historic Madison Square Garden in New York at the 1996 Survivor Series. To the surprise of everyone sitting and watching at home, the “smart” New York fans were heavily behind Sid. Jose Lothario tried to stop Sid from using a camera to hit Shawn but instead, Sid cracked Jose with the camera instead to elicit a massive pop from the crowd. Shawn eventually cracked Sid with Sweet Chin Music. But instead of going for the cover he checked on Lothario, which ended up costing him the match and his title soon after. This might be my favorite Sid match and is definitely considered one of Shawn Michaels’ best matches.

During his initial company runs, Shawn had been in the WWF since the 80s and a full-fledged singles wrestler since 1992. The Undertaker made his legendary WWF debut in 1990. Prepare to have your mind blown when you read this fact – this was the first time the two ever met in a singles match. “The Phenom: was annoyed by HBK’s chicken shit heel antics and still upset that Michaels inadvertently cost him the title at SummerSlam ’97. Shawn was super afraid of ‘Taker, but too arrogant to admit it (because he’s the great HBK, of course). This feud marked a fresh match that fans were heavily invested in.

Both men showcased great chemistry right off the bat and this led to them producing an amazing all-out brawl. Shawn’s offense wasn’t effective on the angry “Deadman” and he found himself running away from ‘Taker on multiple occasions. Triple H and Chyna tried helping Michaels as D-Generation X was slowly forming, but they also suffered from the wrath of The Undertaker. This incredible match ended in a no contest, but that’s because it was really a setup for the next meeting between the two – the first ever Hell in a Cell. I always enjoy watching this, especially for the character work on display here.

The Shawn Michaels and Chris Jericho rivalry in 2008 was one of the best things to come out of professional wrestling that year. It started when Jericho began questioning Shawn’s true character. The fans’ loyalty to HBK remained stable, even though he would cheat or use dirty tactics. This began to get under Jericho’s skin, which slowly turned him into a suit-wearing, bitter heel that would call out the wrestling fans’ hypocrisy. Jericho shockingly threw Shawn through his “Jeritron 5000” monitor and greatly injured his eye (which he further targeted in a match at the 2008 Great American Bash).

Shawn claimed he would have to retire at WWE SummerSlam 2008, but Jericho accidentally struck HBK’s wife that night and pushed Shawn into competing in this wild Unsanctioned Match at WWE Unforgiven 2008. This was a highly entertaining savage brawl that showed a version of Shawn that was clearly thirsty for revenge. It would end in a ref stoppage, but it was so fascinating to see this fired-up and pissed-off version of HBK going at “Y2J” with all guns blazing. The off-the-charts brutality of this bout makes it another one of Shawn Michaels’ best matches.

I always debate if I should add any matches that feature Chris Benoit on my lists considering the tragic way his life ended with the horrific acts that took place. However, I try to separate wrestling from my personal life and my opinions surrounding some of the surly individuals within it. It’s undeniable that Benoit was one of the best professional wrestlers in the world when he was going strong. In 2004, he got to step in the ring with two of the best in Triple H and Shawn Michaels in back-to-back months. This was a rematch of their legendary WrestleMania XX match and it’s arguably almost as good as that one.

This time around Benoit defended the World Heavyweight Championship he won just a month prior. The excellent chemistry between these three Superstars played out wonderfully once again. What’s extra notable about this match is how the show it was featured on (WWE Backlash 2004) took place in Canada, which propped up Benoit the home country favorite. At ‘Mania XX, he made HHH tap out. But in this match, Benoit emerged as the victor by making Shawn tap out with Bret Hart’s iconic Sharpshooter. This was fitting since Canadian fans have always harbored a strong resentment toward HBK for his role in the “Montreal Screwjob.” As far as Triple Threat Matches go, this one deserves mentioning among Shawn Michaels’ best matches.

This was one of the best matches of 1995, which honestly wasn’t a very popular year for the WWF as a whole. Also, Jeff Jarrett hasn’t always been all that favored among wrestling fans because of how unlikable his character managed to be. It’s why I think wrestling fans didn’t start actually appreciating his past work until most recently. Simply put, Jarrett is the master of “go away heat.” However, as more time goes by, we realize just how good of an annoying bad guy he was as well as being a great worker.

Jarret proved to be the perfect WWF foil to make us root for our favorite good guys even more while making them look that much better in the ring. This match is a great example of that. HBK was on his rise as the top babyface in the company and regaining the WWF Intercontinental Championship for the third time was seen as something used to boost his stock even more than before. These two had a great match with a creative finish that saw The Roadie pull “Double J’s” leg instead of Shawn’s by mistake, which allowed Shawn to capitalize on that mistake for the W. This mid-90s IC Championship bout will always stick out as one of Shawn Michaels’ best matches.

This was the rubber match of the Kurt Angle and HBK trilogy that kicked off at WrestleMania 21. At that show, Angle came out on the winning end of their first clash. In their rematch at Vengeance 2005, Shawn got his lick back by beating Angle in yet another great match. When Raw returned to the USA Network in 2005, the WWE hosted a major three-hour “Raw Homecoming” show.

One of the headline matches from that show Angle and HBK facing off against each other in a 30-minute Iron Match to kick off the in-ring portion of the show. One of the biggest problems I have with Iron Man Matches is how they sometimes feel like they drag on. But these two have such great chemistry that the 30 minutes just flew by. The finish of this match ended in a draw of 1-1 and there wasn’t any overtime, which led to Angle frustratingly walking off from the ring. This match marks one of those rare occurrences where a trilogy ended without a definitive winner at the end and the result didn’t bother me that much. Regardless of the end result, this is still one of Shawn Michaels’ best matches.

When HBK and Y2J began feuding at the beginning of 2003, fans bore witness to a dream feud finally coming true. As someone who followed Jericho’s career since he was in WCW, I knew how good of a worker he was. So the idea of him wrestling Shawn got me super excited. The story backing this match centered on Jericho looking up to Shawn during his formative years and recognizing HBK as a huge influence to Y2J when he broke into the wrestling business.

However, the self-proclaimed “King of the World” now believed that he was better than his hero and wanted to prove it on the WrestleMania stage. This first-time meeting featured a simple story being told where Jericho relied on underhanded tactics to get the better of his former idol. Their match at ‘Mania XIX delivered on all the hype and often gets forgotten because it was featured on such a stacked card. Also, their 2008 rivalry and the great matches produced during that feud sometimes overshadow this one. Shawn went over Y2J here, but Jericho ended up being the last one laughing when all was said and done. Not only do we have one of the best ‘Mania matches here, but we also have another of Shawn Michaels’ best matches.

Once again, I debated mentioning these types of matches on this list due to the inclusion of Benoit. But I would feel remiss if I did. Prior to the Benoit tragedy, this was a favorite match for tons of wrestling fans. It might still be a favorite match for a good number of those same fans. HBK and HHH re-ignited their storied rivalry in December of 2003. Benoit won the 2004 Royal Rumble Match and in the process, he jumped over to Monday Night Raw to challenge “The Game” for the World Heavyweight Championship.

Hunter and Shawn wrestled each other at the 2004 Royal Rumble in a Last Match Standing Match that ended in a draw. Shawn pleaded to get another match with HHH so they could bring their bitter feud to an end. But Benoit’s Royal Rumble win and WrestleMania challenge changed up that rematch scenario. This change in storyline led to an incredible Triple Threat Match getting booked for ‘Mania XX. The odds were stacked against Benoit as the former DX stablemates surprisingly worked together to eliminate him, but he just wouldn’t stay down. In the end, Benoit emerged as the new World Heavyweight Champion after a hard-fought and bloody three-man war.

Angle and HBK had an absolute banger at WrestleMania 21 that exceeded all expectations. However, Angle was a SmackDown star and Shawn mainly competed on Raw. So the fans didn’t know if they would cross paths again in the ring until Angle was drafted to Raw. Shawn immediately challenged Angle to a rematch, hoping to redeem himself from his WrestleMania 21 loss. Now it must be said – this match isn’t as good as their ‘Mania 21 match simply because it suffered by being a rematch and that didn’t have the added ambiance of the bright lights brought on by ‘Mmania.

Regardless of those factors, this match is still really good and deserves to be placed so high on this list. Angle was relentless here as he clearly wanted to remain undefeated against HBK. Shawn wanted to win really badly as well to prove to himself that he could beat Angle. Shawn’s masterful selling of his injured ankle was enough to make everyone believe that maybe Angle was going to get the better of him once again. Shawn won this bout by catching Angle with a Sweet Chin Music out of nowhere when Angle went to the top rope in an uncharacteristic move. HBK-Angle 2 will always be regarded as one of Shawn Michaels’ best matches.

This is the third Ladder Match on the list, but the first one I’m featuring from the 2000s. This latest pick comes from the highly praised 2008 rivalry between HBK and Y2J. This feud began in April of that year when Jericho questioned the fans’ hypocrisy as they continued to stay loyal to Shawn, even when he took shortcuts or acted like an egomaniac. Things quickly turned personal when Jericho injured Shawn’s eye and struck his wife on accident, which inspired Shawn to stay un-retired. In September 2008, Shawn beat Jericho in an Unsanctioned Match at Unforgiven. But at the end of that show, Jericho ended up in the World Heavyweight Championship Scramble match and shocked the world by walking out the new champion.

Shawn, who had already gotten his personal revenge, now wanted to enact some professional revenge by taking something away that was precious to Jericho. That precious item was clearly the World Heavyweight Championship. This match started off like your everyday wrestling match before the ladders came into play. That resulted in a bunch of impressive and gnarly bumps being doled out in front of a very appreciative crowd. Lance Cade (RIP) even tried to get involved in all the proceedings. In the end, both men played tug-a-war with the unstrapped belt, only for Jericho to knock HBK off the ladder with a headbutt for the win. That amazing ending and everything that took place before it grants it a high spot on my list of Shawn Michaels’ best matches.

‘Taker badly wanted to get his hands on Shawn, who was an arrogant chickenshit heel for months after HBK inadvertently cost him the WWF Championship at SummerSlam 1997. However, every time he almost got his hands on Shawn, his new DX stablemates in HHH, Chyna, and Rick Rude would either whisk HBK away from certain doom or have the numbers advantage during a beatdown. Their first match at WWF Ground Zero: In Your House ended in a no-contest due to all the outside inferences. For the remainder of that match, Shawn did his best to avoid locking up with ‘Taker (the fans could see right through Shawn’s cocky demeanor because he was visibly too proud to admit that he was afraid of ‘Taker). This led to both men being booked in the first-ever Hell in a Cell Match – this match stipulation was put in place so nobody could interfere and the match could stay contained within the massive cage structure.

This bout is memorable for so many reasons outside of it being the first-ever HIAC Match. It’s still hilarious to watch Shawn trying his best to run away from ‘Taker to the point where he got pulled off the side of the cage to fall on top of an announce table while being chased by his foe. HBK and ‘Taker eventually fought on top of the cell, which seemed super dangerous, especially in 1997. HBK took a hell of a beating at that moment while he struggled to make a comeback. The epic finish came when ‘Taker’s “brother” Kane made his grand debut by confronting and Tombstone Piledriving his sibling. This allowed Shawn to sneak away with the shocking victory.

This bout will forever be held up among the top five Hell in a Cell matches of all time. It’ll most certainly be remembered fondly as one of Shawn Michaels’ best matches.

Following his loss to Austin at WrestleMania XIV in 1998, Shawn retired from in-ring competition due to his severely injured back. Although Shawn stayed on WWF TV as a commissioner and took on other onscreen roles, it sadly seemed as if his in-ring career was truly over. In 2002, Shawn surprised the fans when he made his return to run alongside Kevin Nash as the newest member of the nWo. However, the faction would be disbanded a couple of months after his return due to Nash suffering a devastating quad knee injury.

In the months that followed, HHH made the jump from SmackDown to Raw – this put the two former DX mates back together on the same show. Right when we thought we were going to get a reunion, HHH broke everyone’s hearts when he landed a Pedigree on HBK when it looked like they were in cahoots once more. Later on, the fans learned that Hunter attacked Shawn in an arena parking lot and left him a bloody mess. Those shocking events resulted in both men being booked for an Unsanctioned Street Fight at SummerSlam 2002, which saw Shawn officially come out of retirement.

At the time, this comeback match was expected to be a one-off that would see Shawn slithering back into retirement after facing his best friend. Coming into this match, Shawn noted that he wasn’t so confident that he could perform at the same level he used to. To everyone’s surprise, Shawn looked like he hadn’t missed a step in his four years away from wrestling. This brawl is filled with impactful weapon usage and awesome spots, such as Shawn flying off a ladder to land a sick elbow drop onto HHH.

Shawn ultimately got the win by catching Hunter with a pin out of nowhere rather than nabbing a definitive victory. Post-match, HHH attacked Michaels with a sledgehammer shot to the back to get his heat back and put his former best friend back into retirement. Thankfully, that wouldn’t be the case. This incredible comeback match for HBK is for sure one of Shawn Michaels’ best matches ever.