Shawn Michaels is a big match player! He has earned countless victories in his stellar WWE Hall of Fame career. However, some wins have been bigger than others.
The Heartbreak Kid is arguably viewed by many as the greatest WWE superstar of all time. Michaels' career can be separated into two parts, his pre-1998 career featured three WWF Championship reigns. His second run after a career-threatening back injury from 2002-2010 was sensational.
Michaels has earned the moniker of Mr. WrestleMania, and the Showstopper has had plenty of wins against some of the very best. Let's go down memory lane, and revisit the 10 biggest wins of Shawn Michaels' career.
10 Shawn Michaels Vs Kurt Angle (Vengeance 2005)
2005 was one of Shawn Michaels' best years in the squared circle in terms of big matches. HBK lost to Kurt Angle at WrestleMania 21 in one of the best pure technical wrestling bouts on the Grandest Stage of Them All. Angle was now a member of Raw and the two locked horns once more at Vengeance.
Angle was motivated and determined to earn another win against Michaels. This rematch between the two WWE Hall of Famers was once again off the charts. However, Michaels turned the tables on the Olympic gold medalist, earning a monumental victory over Angle.
9 Shawn Michaels Vs Razor Ramon (SummerSlam 1995)
The WrestleMania X ladder match between Shawn Michaels and Razor Ramon for the Intercontinental Championship was outstanding. Moreover, Michaels and Ramon topped that ladder match at SummerSlam 1995. The Showstopper was the reigning Intercontinental Champion with Ramon as the challenger in another ladder match.
This Intercontinental Championship ladder match ebbed and flowed with both men taking a tremendous amount of bumps. It set the bar for future ladder matches to follow. Both competitors came out strong after this bout, and HBK got his revenge from a year prior, by retaining his Intercontinental Title.
8 Shawn Michaels Vs John Cena (Raw 2007)
In 2007, Michaels was firmly back in the main event title picture at WrestleMania 23. Unfortunately, HBK lost to John Cena in a WWE Championship match which helped elevate Cena as a certified main eventer. Nevertheless, the former World Tag Team Champions clashed a few weeks later on an episode of Raw in London.
This match certainly exceeded their WrestleMania 23 match, this time the WWE Championship was not at stake. The two went almost one hour with Michaels overcoming Big Match John in one of the greatest matches in Raw history.
7 Shawn Michaels Vs Ric Flair (WrestleMania XXIV)
Shawn Michaels' clash with Ric Flair at WrestleMania XXIV in 2008 was one of the most important matches in both former world champion's careers. Mr. WrestleMania was assigned the task of putting the Nature Boy into retirement.
Whilst the match was not one of Michaels' best, the storytelling had the fans invested in this emotional encounter. Flair gave it his all. In the end, The Heartbreak Kid mouthed to Flair, "I'm Sorry I Love You"Â and then nailed the Nature Boy with a Sweet Chin Music. This victory had significance for Shawn as it was his final victory at WrestleMania.
6 Shawn Michaels Vs Triple H (SummerSlam 2002)
For the first time in four years, Shawn Michaels was competing inside the ring at SummerSlam 2002. HBK sustained a career-threatening back injury at the 1998 Royal Rumble, where he herniated two discs. Michaels' first match back in his second run was against none other than Triple H.
Hunter and Michaels were going to reform DX on an episode of Raw in July but Triple H viciously assaulted his former best friend. Their match at SummerSlam was a brutal Unsanctioned match. It seemed as though that Shawn was never away from the ring, as he earned a morale-boosting victory over The Cerebral Assassin. As usual, Michaels stole the show and their match was the best match on the card that night.
5 Shawn Michaels Vs The Undertaker (Badd Blood: In Your House)
In the main event of SummerSlam 1997, Shawn Michaels assumed the role of special guest referee in The Undertaker's WWF Championship match with Bret Hart. Michaels accidentally hit Undertaker with a steel chair and was forced to make the three count for Hart and award him the WWF Championship.
One of the best feuds of the '90s saw Michaels and Undertaker compete in the first-ever Hell in a Cell match at Badd Blood: In Your House. The stakes were high as the winner would face Bret at Survivor Series for the WWF Championship. Despite taking a nasty bump and falling through the table, HBK recovered with a huge assist from Kane, who made his debut. Michaels covered The Deadman to head towards Survivor Series.
4 Shawn Michaels Vs Bret Hart (Survivor Series 1997)
Survivor Series 1997 was the final encounter in the storied rivalry between Shawn Michaels and his bitter rival Bret Hart. Hart was the reigning WWF Champion and was on his way out to WCW. However, the Hitman did not mind dropping the title but did not want to lose the championship in Montreal.
Despite their well-documented personal dislike for each other, on and off-screen, Michaels and Hart did not fail to disappoint with a quality WWF Championship bout. The Heartbreak Kid was thriving in his role as a heel, and he locked Bret in the Sharpshooter. Thus, the Montreal Screwjob was born as referee Earl Hebner rang the bell. Any win over Bret was major for Michaels, who left the arena to a chorus of boos with his third and final WWF Championship in tow.
3 Royal Rumble 1996
Michaels made history at the 1995 Royal Rumble by becoming the first man to win the Royal Rumble match as the number one entrant. HBK suffered heartbreak as he failed to capture the WWF Championship in his title match with Diesel at WrestleMania XI. Nevertheless, Shawn was determined to main event WrestleMania and attain his goal of becoming WWF Champion.
The Showstopper was the standout performer in the 1996 Royal Rumble match. He entered 18th and eliminated an astonishing eight combatants. Michaels ended Diesel's dreams of regaining the WWF Title as HBK eliminated Big Daddy Cool to claim his second successive Royal Rumble victory. It was a career-defining moment for HBK, who went to face Bret Hart at WrestleMania XII.
2 Shawn Michaels Vs Triple H Vs Chris Jericho Vs Booker T Vs Kane Vs Rob Van Dam (Survivor Series 2002)
After defeating Triple H at SummerSlam 2002, Michaels was looking to back up his victory at Survivor Series. This time the stakes were much higher as The Game defended the World Heavyweight Championship in the first-ever Elimination Chamber match.
Triple H's World Heavyweight title was in major jeopardy as he defended the championship against HBK, Chris Jericho, Booker T, Rob Van Dam, and Kane at Madison Square Garden. Despite being the final entrant, Michaels eliminated Jericho and was in the final two with The Game. The Heartbreak Kid nailed Triple H with Sweet Chin Music to clinch his first World Championship in four years. It was Michaels' fourth and final reign as World Champion but solidified his return hugely. HBK is also the first man to win the inaugural Hell in a Cell and Elimination Chamber matches.
1 Shawn Michaels Vs Bret Hart (WrestleMania XII)
Shawn Michaels' 1996 Royal Rumble victory guaranteed his spot in the main event of WrestleMania XII for the WWF Championship. HBK challenged Bret Hart for the WWF Championship in the first-ever 60-minute Iron Man match. Michaels was hoping to go one better from last year's narrow defeat to Diesel.
Michaels' in-ring skills had improved immensely and he was poised to make a run as WWF Champion. To Bret's credit, his professionalism was second to none as he made Shawn look like that he can hang in the big leagues. Their WWF Championship encounter was one of the best title matches in WrestleMania history.
After 60 minutes had expired, Michaels nailed Bret with Sweet Chin Music in overtime. Thus, the boyhood dream finally came true with Michaels winning his first WWF Championship. It finally put him in the upper echelons in the WWE and it is certainly the biggest win of his career, which put him on the map as a certified main eventer.