Countdown To WWE Wrestlemania 33 #16: Top 10 Shawn Michaels Matches In ‘Mania History

Every day from March 1 until WWE Wrestlemania 33 on April 2, Fightful will be bringing you the Countdown To WWE Wrestlemania 33. Each day, you will be getting a top 10 list or an event preview or statistics/figures from past ‘Mania events and everything in between.


In today’s column, we will be taking a look at the Top 10 Shawn Michaels Matches In ‘Mania History. They call him “Mr. Wrestlemania” and that’s for a good reason, which is why we are celebrating the great HBK matches in ‘Mania history.

#10: Shawn Michaels vs. Tito Santana (‘Mania 8)

If you wanted a lone event that pointed to the birth of “The Heartbreak Kid,” then look no further than WWE Wrestlemania 8. This was the first major singles match for HBK following a heel turn after throwing Marty Janetty through the window during the Barber Shop talk show. The match was also the last big match for Santana at ‘Mania, who had been competing at the event since the first ‘Mania. HBK would win the match after nailing Santana with a super kick, which was dubbed “Sweet Chin Music” by Michaels.

#9: Shawn Michaels vs. Vince McMahon - No Holds Barred Match (‘Mania 22)

Much like Vince’s match with Hulk Hogan at ‘Mania 19, the battle with Shawn Michaels was another bout that was a lot better than it should’ve been. The match also featured plenty of interference from The Spirit Squad and from Shane McMahon as well. This was the typical Vince McMahon match, with plenty of blood, violence and weapons from bell to bell. HBK would walk away victorious by nailing Vinnie Mac with some Sweet Chin Music and an elbow drop through a table from the top of a ladder.

#8: Shawn Michaels vs. Ric Flair - Career Threatening Match (‘Mania 24)

This match was great and all, but once it was over, I was left wondering what would’ve happened if we got a prime HBK versus a prime Ric Flair. This match was for Flair’s career, which had been on the line for months now and Flair had been victorious until this point. This match showed that HBK was still one of the greatest performers of all time, while Flair was still awesome in his old age. The match may be best remembered for the post-match moments with Flair and his family, plus the next night on Raw was memorable as well.

#7: Shawn Michaels vs. Chris Jericho (‘Mania 19)

For the first time in five years, Michaels returned to ‘Mania and he faced off with one of the greatest workers of all time in Chris Jericho. This match was a technical wrestling masterpiece, with HBK showing that he hadn’t lost a step since his last ‘Mania appearance. Michaels would win the match after catching his Canadian counter part with a roll up from out of nowhere. The post-match was great as well, with a teary eyed Y2J pretending to embrace HBK before nailing him with a low blow.

#6: Shawn Michaels vs. Chris Benoit vs. Triple H (Champion) - WWE Title Match (‘Mania 20)

In an odd way, HBK would be the odd man out in a match that gave hardcore wrestling fans one of the most glorious endings of all time. HBK engaged in a classic alongside Triple H and Benoit, it was only his second ‘Mania since returning from retirement. This was also the first ‘Mania that HBK headlined since WWE Wrestlemania 14, where he lost to Steve Austin. Michaels didn’t win the title on this night, Benoit did, but this match was still a classic for the ages.

#5: Shawn Michaels vs. Bret Hart (Champion) - WWE Title Match - 60 Minute Iron Man Match (‘Mania 12)

‘Mania 12 was a three hour show on pay-per-view, with over an hour of that show dedicated to the Ironman Match between WWE Champion Bret Hart and Shawn Michaels. The two battled back and forth for an hour with nobody scoring a single fall, then headed into sudden death overtime.The match was won, Michaels nailed Hart with Sweet Chin Music to score the lone fall in the match and win the title. Say whatever you want about the booking and the lack of falls, but Hart and Michaels went over an hour in a ‘Mania main event that is still remembered over two decades later.

#4: Shawn Michaels vs. Kurt Angle (‘Mania 21)

There was a moment in the Royal Rumble Match a few months earlier where Kurt Angle and HBK eliminated each other from the match. The feud began and all the wrestling fans eyes lit up with glee because we knew what was coming for us at Wrestlemania. The match between arguably two of the greatest wrestlers in WWE history may be one of the best matches of all time, not just at a ‘Mania. Angle walked away victorious when it was all said and done, but it was actually the wrestling fans in attendance and who watched the match on pay-per-view who were the real winners that night.

#3: Shawn Michaels vs. The Undertaker (‘Mania 25)

It should have been criminal that a match that was this good wasn’t the main event of the show--Triple H versus Randy Orton had that honor on this night. The match was also the prelude to one of the greatest matches in the history of the event, which you can check out a little later. The match between these two legends of the business had everything a wrestling fan could ever hope for. The Undertaker would walk away victorious on this night, which was a prelude to what we would get a year later.

#2: Shawn Michaels vs. Razor Ramon (Champion) - WWE Intercontinental Title Match - Ladder Match (‘Mania 10)

The first Ladder Match in ‘Mania history took place at ‘Mania 10 as Shawn Michael and Razor Ramon battled to see who would become the undisputed WWE Intercontinental Champion. This match was an instant classic, as both wrestlers took a beating that certainly left them bruised and hurting for weeks afterwards. Razor would become the undisputed champion that night, which was also the ‘Mania debut of Diesel, better known to some wrestling fans as Kevin Nash. The two would duel in a ladder match again a few years later at WWE Summerslam ‘95, but it wouldn’t measure up to the standards the first match set.

#1: Shawn Michaels vs. The Undertaker - Career vs. The Streak Match (‘Mania 26)

The two clashed before at ‘Mania 25, but this would arguably be the greatest match in each wrestler's respective career. While both battled in their home state of Texas the year before, this battle between the two legends took place in Arizona. The match was a true masterpiece of wrestling greatness and for one wrestler, it would be their final match ever. The Undertaker defeated Michaels in the match, ending the career of the one dubbed “Mr. Wrestlemania.”

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