Two-time WWE Hall of Famer Shawn Michaels is one of the greatest wrestlers of all time. Michaels isn't just a good in-ring performer, he is an entertainer. Michaels has feuded with some of the best wrestlers in WWE history, and some of the storytelling has been magnificent. Michaels has generally featured in the main event scene with some of his programs garnering a lot of interest.
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As expected in rivalries there are a series of matches that Michaels has contested. Not all of the matches that Michaels featured in were great, but the majority were brilliant matches, and these are the best that the Showstopper had with his greatest rivals.
10 Randy Orton: Survivor Series 2007
Shawn Michaels and Randy Orton's rivalry began in 2003 when Orton was a member of Evolution. Orton stunned Michaels at Unforgiven, and he earned a victory over Michaels in a traditional Survivor Series elimination match at Survivor Series.
Michaels and Orton rekindled their rivalry in 2007, and they clashed over the WWE Championship at Survivor Series. This was their best match together, and Orton saw off Michaels to retain the WWE Championship in a high-quality match.
9 Marty Jannetty: Raw (7/19/93)
The Rockers imploded when Shawn Michaels smashed Marty Jannetty's head through Brutus "The Barber" Beefcake's mirror in the barbershop. Michaels and Jannetty became singles competitors and they clashed over the Intercontinental Championship for parts of 1993.
They had a pay-per-view quality match on the July 19, 1993 edition of Raw. It was a back-and-forth contest, but Michaels overcame Jannetty to successfully defend the Intercontinental Championship.
8 Steve Austin: King Of The Ring 1997
Shawn Michaels and Steve Austin won the WWE World Tag Team Championship from Owen Hart and The British Bulldog in May 1997. However, they couldn't work as a cohesive unit. Michaels and Austin squared off at King of the Ring, a month after they won the Tag Team Championship.
Michaels and Austin had a fantastic wrestling match at King of the Ring. They couldn't be separated with the match going to a double disqualification. Unquestionably, their WWE Championship match at WrestleMania 14 was the bigger bout, but Michaels had a severe back injury that limited his performance with Austin going to win his first WWE Championship. Their meeting at King of the Ring was better than 'Mania a year later.
7 Kurt Angle: WrestleMania 21
Shawn Michaels and Kurt Angle were on separate brands when they began feuding in early 2005. At WrestleMania 21, fans were treated to one of the best matches in the history of WrestleManiawith Michaels and Angle going head-to-head.
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Michaels and Angle tore the house down with the Olympic Gold Medalist forcing Michaels to submit to the Angle Lock. The rivals were both on Raw by the time summer came around and they had a rematch at Vengeance, which was high-quality and Michaels flipped the script and saw off Angle.
6 Diesel: In Your House, Good Friends, Better Enemies (1996)
Shawn Michaels and his former bodyguard Diesel were rivals in early 1995, and Michaels won the first of his two Royal Rumble matches in January 1995. The Heartbreak Kid challenged Diesel for the WWE Championship but he was unable to beat Big Daddy Cool for the title at WrestleMania 11.
13 months later, Michaels was the reigning WWE Champion and he defended the title against Diesel at In Your House: Good Friends, Better Enemies before Diesel headed to WCW. This was a solid match and it was a good start to Michaels' WWE Championship title reign.
5 Razor Ramon: WrestleMania 10
The rivalry between Shawn Michaels and Razor Ramon was legendary in the New Generation Era. At WrestleMania 10, Michaels and Ramon stole the show in an excellent ladder match to crown the undisputed Intercontinental Champion.
The Bad Guy won the match, but that wasn't their only ladder match against each other. They had another solid ladder match at SummerSlam 1995 with the Intercontinental Championship at stake, and Michaels got his revenge by retaining the title.
4 Chris Jericho: No Mercy 2008
Shawn Michaels and Chris Jericho feuded several times in the 2000s and they created magic when they went toe-to-toe. They had a barnburner match of a match at WrestleMania 19, but they managed to top that when they contested a ladder match for Jericho's World Heavyweight Championship at No Mercy 2008.
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Their feud was the rivalry of the year, and their ladder match was a perfect way to bring the curtain down on their rivalry. Jericho fought hard and he was bleeding from the mouth, after headbutting Michaels, Jericho retained the World Heavyweight Championship by retrieving the title.
3 The Undertaker: WrestleMania 25
Shawn Michaels and The Undertaker brought out the best in each other, and while fans talk about their back-to-back WrestleMania epics, their feud began in 1997. Michaels and Undertaker competed in the inaugural Hell in a Cell match, and all thanks to outside interference from Kane, Michaels was triumphant.
Michaels sustained a career-threatening back injury in their casket match for Michaels' WWE Championship at the 1998 Royal Rumble. Nevertheless, Michaels returned to WWE in 2002, and fans were treated to seeing Michaels and Undertaker facing off at WrestleMania 25 and WrestleMania 26. Their WrestleMania 25 encounter was superb with Undertaker prevailing, and at WrestleMania 26, Undertaker sent Michaels into retirement in the main event.
2 Triple H: SummerSlam 2002
Shawn Michaels and Triple H were best friends but the Game turned heel by attacking Michaels in the summer of 2002. This led to Michaels and Triple H having Michaels' first in-ring match in four years at SummerSlam.
Michaels battled past his former DX stablemate in an Unsanctioned match. Furthermore, Michaels and Triple H have had several high-stake battles including a Last Man Standing match and a Hell in a Cell match. but none of those matches topped their SummerSlam encounter.
1 Bret Hart: Survivor Series 1997
Unquestionably, Shawn Michaels' biggest rival is Bret Hart, they had a personal disdain for each other that made their rivalry feel real. They've faced off countless times, and they clashed over the WWE Championship at Survivor Series 1992 in a match that Hart won.
Their WWE Championship match at WrestleMania 12 was significant as Michaels was victorious with the boyhood dream coming true with Michaels winning the WWE Championship for the first time. However, their meeting at Survivor Series 1997 was controversial as it was the infamous Montreal Screwjob with Michaels cinching in the Sharpshooter and Hart not tapping out with Michaels awarded the WWE Championship for the third time.
