Two-time WWE Hall of Famer Shawn Michaels is one of the greatest wrestlers of all time. Michaels has earned the moniker "Mr. WrestleMania" as he always brings his A-game on the Grandest Stage of Them All. HBK is a four-time WWE World Champion with all four of his World Championship wins coming on pay-per-view. Michaels has generally been protected in his WWE career as he has racked up plenty of wins on a PPV.
Whilst, Michaels may have picked up a lot of victories on a WWE PPV, he isn't exempt from losing a few matches on a pay-per-view. Some of the biggest stars in the industry have got one over on Michaels in one-on-one competition on a PPV which isn't a mean feat.
Note: Shawn Michaels' losses to Tatanka at WrestleMania 9 and Ken Shamrock at D-Generation X: In Your House get honorable mentions as they beat Michaels respectively by count-out and disqualification in championship matches.
15 Bret Hart
The first singles encounter between Shawn Michaels and Bret Hart on a WWE pay-per-view was at Survivor Series 1992. The stakes were high as the Hitman's WWE Championship was on the line, and HBK was bidding to become a double champion as he was the reigning Intercontinental Champion.
They stole the show in one of the greatest WWE Championship matches in the '90s. They closed out the show, and Hart handed Michaels his first singles loss on a WWE pay-per-view after Michaels was unable to fight out of the Sharpshooter.
14 Razor Ramon
Ladder matches and WrestleMania go hand in hand. The first televised Ladder match took place at WrestleMania 10 with Shawn Michaels and Razor Ramon battling to become the Undisputed Intercontinental Champion. Their collision course was in the hallowed halls of Madison Square Garden, and they knocked it out of the park.
The fans in attendance were heavily invested, and there was a brilliant atmosphere throughout the match. HBK went home disappointed as the Bad Guy clinched the two Intercontinental Championships that hung in the balance with Michaels unable to stop him.
13 Diesel
Shawn Michaels won the 1995 Royal Rumble match, and he challenged his former bodyguard Diesel for the WWE Championship at WrestleMania 11. The duo was unfortunate not to headline WrestleMania, but they constructed a decent championship match.
Diesel dominated the championship match, but Michaels did have his chance to beat Diesel for the title. Michaels gave it his all, but he was unable to fulfill his boyhood dream which would come a year later.
12 Sycho Sid
Shawn Michaels was eight months strong into his maiden WWE Championship reign, and he put the title on the line against Sycho Sid at Survivor Series 1996. Despite being the babyface, HBK was booed by the fans in Madison Square Garden.
Michaels and Sid produced a competitive WWE Championship match, and it wasn't short of controversy. Michaels' manager Jose Lothario was knocked to the floor, and Sid captured the WWE Championship for the first time by overcoming HBK after he systematically broke him down.
11 Steve Austin
WrestleMania 14 featured Shawn Michaels defending the WWE Championship against Steve Austin. This had the potential to be an instant classic but HBK was in an insurmountable amount of pain with a severe back injury.
Michaels did his best and he grimaced throughout the match. Relief would have set in for Michaels once he dropped the WWE Championship to Austin, and he took his four-year sabbatical from the squared circle.
10 Triple H
Former buddies in DX, Shawn Michaels, and Triple H were at loggerheads in a rivalry that spanned from 2002-04. Triple H picked up his first singles victory over Michaels on a WWE pay-per-view at Armageddon 2002 to regain the World Heavyweight Championship in a Three Stages of Hell match.
Their Hell in a Cell match was off the charts at Bad Blood 2004, and they battled for 45 minutes. Triple H was victorious, and he successfully retained the World Heavyweight Championship against Michaels at Taboo Tuesday 2004.
9 Ric Flair
Everyone remembers Ric Flair and Shawn Michaels' emotional epic at WrestleMania 24, but they faced-off at Bad Blood 2003 too. Michaels was feuding with Evolution, and he battled with Naitch in a match that is forgotten about.
Michaels put Flair through a table on the outside. Randy Orton got involved after HBK took Flair down with Sweet Chin Music. Orton hit Michaels with a steel chair, and he placed Flair onto Michaels to secure the victory.
8 Randy Orton
It was "Legend vs. Legend Killer" at Unforgiven 2003 when Randy Orton collided with Shawn Michaels. This was a magnificent wrestling match, and Orton scored a handy victory over Michaels with some help from brass knuckles.
Their second encounter on a WWE pay-per-view was at Judgment Day 2007, and it was an abrupt match with HBK dealing with a legitimate injury. Orton earned his third win over Michaels on PPV at Survivor Series 2007 in a fantastic WWE Championship match with his patented RKO.
7 Edge
Edge and Shawn Michaels collided in the curtain raiser at the 2005 Royal Rumble. Edge was seething as Michaels had cost him a chance at winning the World Heavyweight Championship inside the Elimination Chamber at New Year's Revolution.
This bout is often overlooked, but it was a remarkable match with two exceptional workers going toe-to-toe. Edge was on his way to becoming a top star in WWE, and he reversed a roll-up, and he used the ropes for leverage which saw Edge earning one of the biggest wins in his career.
6 Kurt Angle
Fans were in store for a treat when Kurt Angle and Shawn Michaels tore the house down in a wrestling clinic at WrestleMania 21. The Olympic Gold Medalist represented SmackDown, and Michaels was a member of Raw. The reversals and near falls had fans on the edge of their seats.
Angle incorporated his physical style into this bout, and he had a refusal to stay down. HBK gave it his all, but Angle locked in the Angle Lock with Michaels scratching and clawing, but he could not withstand the pain anymore with Angle victorious.
5 Hulk Hogan
SummerSlam 2005 was headlined by two former WWE Champions Shawn Michaels and Hulk Hogan. The Hulkster was no longer functioning at the peak of his powers with injury problems. However, Michaels oversold every time Hogan had some offense.
It was embarrassing, and their match had the potential to be miles better. Nevertheless, it's no surprise that Hogan was the victor in their only meeting.
4 John Cena
Shawn Michaels headlined a one-on-one match at WrestleMania for the first time in nine years. He challenged John Cena for the WWE Championship at WrestleMania 23. This was an amazing WWE Championship match with both men busted wide open.
They were the reigning World Tag Team Champions, but that did not stop them from throwing the kitchen sink at each other. Michaels had his chances, but Big Match John retained the WWE Title with Michaels submitting to the STF.
3 Batista
The rivalry between Batista and Shawn Michaels kick-started after HBK sent Ric Flair into retirement at WrestleMania 24. HBK was triumphant at Backlash 2008, and they had another high-profile rematch at One Night Stand 2008 in a Stretcher match.
This was a superb Stretcher match, and both had a lot of offense in this contest. Chris Jericho would get involved in proceedings. Ultimately, Batista avenged Flair's defeat, and he pushed Michaels across the stretcher to pick up the win.
2 Chris Jericho
Chris Jericho and Shawn Michaels' feud was unquestionably the rivalry of the year in 2008. Jericho turned heel in the summer, and they were on for a collision course at The Great American Bash. Michaels shed buckets of blood in their match, and Jericho was the victor by TKO.
They met several times in 2008, and their Ladder match at No Mercy for the World Heavyweight Championship was the culmination of their feud. It was one of the greatest Ladder matches in WWE history, and Jericho retained his championship after he headbutted Michaels, and he clinched the Big Gold Belt.
1 The Undertaker
Shawn Michaels and The Undertaker had some excellent tussles in the late 90s, but they were involved in two elite WrestleMania matches in back-to-back years in 2009 and 2010. How Dave Meltzer did not give their WrestleMania 25 match, five stars is a mystery to this day. That was wrestling at its peak with Undertaker picking up his first pay-per-view singles win over Michaels.
A year later, their WrestleMania 26 bout had everything riding on it. Michaels' career as well as Undertaker's unbeaten WrestleMania record were on the line. Undertaker's jumping Tombstone Piledriver consigned Michaels into retirement in an emotionally fueled battle.