Originally starting as a tag team competitor with Marty Jannetty as The Rockers, Shawn Michaels broke out on his own in 1992 as a singles star and he never looked back. Michaels is one of the greatest wrestlers of all time, and he is a four-time WWE World Champion. However, Michaels had success at the Royal Rumble first which led to him having major success at WrestleMania.The Heartbreak Kid is a two-time Royal Rumble match-winner. He won the Rumble in back-to-back years in 1995, and 1996, becoming the second of three men to pull off this remarkable feat. Michaels' a prolific performer at the Royal Rumble, and he generally does well at the Rumble with a couple of forgettable performances on his resume.
12 1990
The 1990 Royal Rumble match was by far Shawn Michaels' worst performance in a Royal Rumble match. HBK entered as the 26th participant, and he would have fancied his chances of going on a deep run.
He went after Rick Martel and he nailed him with a few blows but that's as good as it got for Michaels. The Ultimate Warrior grabbed Michaels by the hair and he flung him over the top rope with Michaels' cameo lasting a measly 12 seconds.
11 2003
For the first time in seven years, after winning the Royal Rumble for the second time in 1996, Shawn Michaels participated in a Royal Rumble match. HBK had to take a scenic route once more as he entered the 2003 Royal Rumble match from the unenviable number one position.
Michaels was expecting Chris Jericho to walk down the aisle but it was a ruse with Christian appearing at the top of the ramp. Jericho took advantage by sneaking up behind Michaels, and he viciously assaulted him and eliminated him within the first three minutes.
10 1989
Shawn Michaels made his Royal Rumble match debut at the 1989 Royal Rumble. HBK was a member of The Rockers and he joined the fray as the ninth participant. He avoided trouble early on as Mr. Perfect attempted to eliminate him.
Jake "The Snake" Roberts was already eliminated but he returned with his snake, Damien. Nevertheless, HBK had a respectable performance as he survived 14 minutes. Alongside Marty Jannetty, they eliminated Ron Bass. Michaels nailed Arn Anderson with Sweet Chin Music when the Enforcer entered the ring. However, Michaels was removed from the equation by Anderson and Randy Savage.
9 1992
Shawn Michaels entered the 1992 Royal Rumble match as a newly minted heel after he betrayed Marty Jannetty. HBK received a chorus of boos on the way to the ring. Moreover, Michaels wasn't bothered in the slightest as the winner of the 1992 Royal Rumble match would win the WWE Championship.
HBK nailed eventual winner Ric Flair with Sweet Chin Music early on, and he nailed the British Bulldog with one. Michaels endured 15 minutes until he and Tito Santana eliminated each other.
8 2005
The 2005 Royal Rumble match ended up setting up Shawn Michaels' marquee WrestleMania 21 match. HBK entered the Royal Rumble match as the 19th entrant. Michaels immediately went after Edge who beat him in a match at the start of the night.
He clotheslined Charlie Haas over the top rope, and Kurt Angle attempted to apply the Angle Lock. Michaels countered it and he eliminated him with Sweet Chin Music. An irate Angle re-entered the ring and he eliminated Michaels and brutalized him which set up their legendary WrestleMania 21 encounter.
7 2006
Shawn Michaels was determined to headline WrestleMania once again, and he drew the 25th spot in the 2006 Royal Rumble match. HBK endured just under 13 minutes, and he upped the pace in the match.
He eliminated Trevor Murdoch, both members of MNM, and he executed a superb Sweet Chin Music on Shelton Benjamin to send him packing. Bad news spelled for Michaels when "No Chance in Hell" blared through the speakers with Mr. McMahon coming down the ring. He distracted Michaels and his son Shane who wasn't involved in the Rumble, dumped Michaels out of the Rumble.
6 2008
Just the way the 2007 Royal Rumble match ended, Shawn Michaels and The Undertaker kickstarted the 2008 Royal Rumble match. HBK was the second entrant, and he slugged it out with the Phenom.
Michaels' nose was bloody but that did not stop him from eliminating Shelton Benjamin from the Royal Rumble match for the third consecutive year with Sweet Chin Music. Moreover, he eliminated Undertaker with Sweet Chin Music to prevent him from winning two Rumbles in succession, and Mr. Kennedy sneaked up behind HBK to eliminate him from the bout.
5 1994
Shawn Michaels competed in the 1994 Royal Rumble match, and he produced a superb performance. The Showstopper joined the fray as the 18th participant, and he had a huge impact on the Rumble.
He almost lasted half an hour and he eliminated his former tag team partner Marty Jannetty. Alongside Bret Hart, they eliminated Thurman "Sparky" Plugg, and he eliminated Diesel and Mabel although he had a huge helping hand. Ultimately, Michaels came narrowly close to winning the Rumble but he finished as runner-up with Lex Luger eliminating him, and Luger and Bret were co-winners of the 1994 Royal Rumble match.
4 2010
After losing to The Undertaker in an instant classic at WrestleMania 25, Shawn Michaels was obsessed with a rematch with Undertaker, who was the reigning World Heavyweight Champion. Michaels entered the 2010 Royal Rumble match and he was the 18th entrant once again.
Michaels took no prisoners, and Ted DiBiase, Cody Rhodes, John Morrison, Carlito, Drew McIntyre, and not even his own tag team partner Triple H was safe from elimination as HBK took them out of his way. Unfortunately, he failed to win the Rumble for the third time as Batista shattered his dreams in Michaels' final Rumble appearance.
3 2007
10 years after winning the WWE Championship for the second time at the 1997 Royal Rumble, the Royal Rumble in 2007 once again took place in Shawn Michaels' hometown of San Antonio, Texas. HBK had the hometown support and he was looking to have another memorable night at home.
He was the 23rd entrant, and he eliminated both Finlay and Shelton Benjamin from the Rumble. However, Rated-RKO was looking to take out Undertaker but Michaels intervened by launching Randy Orton over the top rope and he executed the Sweet Chin Music on Edge for a further two eliminations. Ultimately, the finish between Michaels and Undertaker was magical as it was a war of attrition with the legends going back and forth, but the Demon of Death Valley avoided the Sweet Chin Music to secure his maiden Rumble triumph.
2 1996
Shawn Michaels was aiming to become the second man to win back-to-back Royal Rumble matches. The Heartbreak Kid entered the 1996 Royal Rumble match as the 18th entrant, and once again he was the standout performer.
Michaels was now a babyface, and he was a huge draw with the fans. Michaels eliminated an outstanding eight wrestlers, and most importantly he finished off Diesel with Sweet Chin Music to send him over the top rope to secure his second Rumble win, and he went on to capture the WWE Championship from Bret Hart at WrestleMania 12.
1 1995
The 1995 Royal Rumble match was the shortest 30-man Royal Rumble match in WWE history as every entrant entered within 60 seconds. Nevertheless, Shawn Michaels and The British Bulldog began proceedings as the number one and two participants respectively.
Michaels' physical conditioning is outstanding and it made logical sense for him to last the course. HBK eliminated eight wrestlers for the first time in a Rumble, and he capitalized on Bulldog's error think that he had won the Rumble. Michaels sneaked up behind Bulldog and pushed him off the top rope to win the Royal Rumble match for the first time in his career.