26. Hulk Hogan vs The Rock (WrestleMania 18)
In this matchup between of the two biggest names in the business, the Rock bested Hogan in front of a record 68,237 fans. The “Icon vs. Icon” match didn’t feature the two wrestlers at the peak of their powers, but the up-and-down bout electrified the crowd.
Result: The Rock defeated Hollywood Hulk Hogan.
Photo: WWE
25. Triple H vs Shawn Michaels (SummerSlam, 2002)
In his first match in four years, Michaels returned to fight his former best friend, Triple H. The friends-turned-rivals battled it out in the ring, but the real action didn't happen until Triple H hit Michaels with a sledgehammer after the match.
Result: Michaels defeated Triple H in an Unsanctioned Street Fight.
Photo: WWE
24. Ric Flair vs Shawn Michaels (WrestleMania 24)
This bout between two Hall of Fame wrestlers past their prime was one of the most legendary matches ever. Michaels was initially hesitant to beat the Nature Boy, but after three Sweet Chin Musics, Michaels finally pinned the Nature Boy after saying, “I’m sorry, I love you.”
Result: Michaels defeated Flair in a Career Threatening Match.
Photo: WWE
23. The Undertaker vs Shawn Michaels (Badd Blood: In Your House, 1997)
In the inaugural Hell in a Cell match, the Heartbreak Kid and the Phenom showed how fun and brutal this kind of match can be. Although ‘Taker was dominating the match, his undead brother, Kane, made his debut and screwed over his sibling.
Result: Michaels defeated Undertaker to be the No. 1 contender for the WWF World Heavyweight Championship.
Photo: WWE
22. Ric Flair vs Randy Savage (WrestleMania VIII)
Before battling it out at WrestleMania VIII, Flair decided to play mind games with Savage. All it did, however, was motivate Savage to batter the Nature Boy and win the title.
Result: Savage defeated Flair for the WWF World Heavyweight Championship.
Photo: WWE
21. Triple H vs Cactus Jack (Royal Rumble, 2000)
Prior to the big Royal Rumble match in 2000, Triple H and Mick Foley (as Cactus Jack) battled it out in a Street Fight for the WWE Championship. While chairs, thumbtacks and a barbed wire two-by-four were used in the bloody brawl, it was Triple H's Pedigree that wound up ending Jack's shot at the title.
Result: Triple H defeated Cactus Jack to retain the WWF Championship.
Photo: WWE
20. John Cena vs Brock Lesnar (Extreme Rules, 2012)
In his first match since 2004, Lesnar bloodied Cena with devastating elbows. Somehow, Cena was able to survive the punishment long enough to hit Lesnar with an Attitude Adjustment... right into the metal steps.
Result: Cena defeated Lesnar.
Photo: WWE
19. John Cena vs AJ Styles (Royal Rumble, 2017)
In one of Cena's greatest matches, he needed multiple finishers--including an Attitude Adjustment from the top rope--to defeat the champion, AJ Styles. Cena's victory tied Ric Flair's record with his 16th world title reign.
Result: Cena defeated Styles to win the WWE Championship.
Photo: WWE
18. Royal Rumble Match, 1992
This epic Royal Rumble match had even higher stakes than usual, with the winner becoming the WWF World Heavyweight Championship. The roster of 30 wrestlers was completely stacked with old and new stars. In the end, The Nature Boy bested Sid Justice, Hulk Hogan and Randy Savage.
Result: Ric Flair won the WWF World Heavyweight Championship by eliminating Sid Justice.
Photo: WWE
17. Shawn Michaels vs Kurt Angle (WrestleMania 21)
For nearly 30 minutes, two of the best technical wrestlers of all time went head to head. Both men kicked out of multiple pin attempts, but in the end, Angle finally secured an ankle lock on the Heartbreak Kid.
Michaels earned a standing ovation after the bout.
Result: Angle defeated Michaels by submission.
Photo: WWE
16. Bret Hart vs Owen Hart (WrestleMania X)
In a bitter battle between brothers, the Hart siblings battled in the first televised match of WrestleMania X. Owen got the better of Bret by escaping multiple submission holds to win.
Bret--performing double duty--would go on to beat Yokozuna for the WWF World Heavyweight Championship in the main event.
Result: Owen Hart defeated Bret Hart.
Photo: WWE
15. The Undertaker vs Shawn Michaels (WrestleMania XXVI)
Billed as a “Streak vs Career” bout, this no-disqualification main event at WrestleMania 26 was one for the books. After numerous finishers by both men, ‘Taker finally hit his third Tombstone Piledriver, winning his 18th straight match at WrestleMania and ending the Heartbreak Kid’s wrestling career.
Result: The Undertaker defeated Michaels in a No DQ Streak vs. Career Match.
Photo: WWE
14. Bret Hart vs Shawn Michaels (WrestleMania XII)
In this Iron Man Match at WrestleMania XII, sixty minutes wasn’t enough to determine a winner between bitter rivals Hart and Michaels. The match ultimately headed to sudden death where the Heartbreak Kid scored his Sweet Chin Music finisher on the Hitman to win the title.
Result: Michaels defeated Hart in sudden death overtime to win the WWF World Heavyweight Championship.
Photo: WWE
13. John Cena vs CM Punk (Money in the Bank, 2011)
Vince McMahon was desperate for Cena to defeat CM Punk at Money in the Bank 2011. After McMahon and John Laurinaitis interfered in the match, Cena could have had an easy victory but he decided to try win it fair and square. That plan backfired when Punk hit his finisher and won the WWE Championship. He then disposed of Albert Del Rio who tried to use his Money in the Bank power.
Result: CM Punk defeated Cena for the WWE Championship.
Photo: WWE
12. Bret Hart vs The British Bulldog (SummerSlam, 1992)
Although the Intercontinental title was known as the No. 2 WWF title at the time, this bout between the British Bulldog and Hart was the main event at Summerslam in 1992. After the British Bulldog escaped the Sharpshooter submission, he countered and pinned Hart to win the championship.
Result: The British Bulldog defeated Hart for the WWF Intercontinental Championship.
Photo: WWE
11. The Ultimate Warrior vs Randy Savage (WrestleMania VII)
In arguably the greatest retirement match ever, The Ultimate Warrior survived five Savage elbow drops to end the illustrious wrestling career of the Macho Man.
Result: The Ultimate Warrior defeated Savage.
Photo: WWE
10. Shawn Michaels vs Mankind (Mind Games, 1996)
Although the WWF was struggling to keep up with WCW in 1996, the former had Michaels, arguably the world’s best wrestler, at the height of his powers. The Heartbreak Kid showed a more ruthless and calculated persona in this bout with the deranged Mankind. This match elevated both their careers to new levels.
Result: Michaels defeated Mankind by disqualification.
Photo: WWE
9. Edge And Christian vs The Dudley Boyz vs The Hardy Boyz (WrestleMania 17)
Dubbed “TLC II,” this Tables, Ladders and Chairs match featured three of the best tag teams of the era in a high-flying fight that saw spears, Swanton Bombs, and more. Eventually, Edge and Christian outlasted their opponents in one of the craziest battles in WrestleMania history.
Result: Edge and Christian defeated The Dudley Boyz and The Hardy Boyz for the WWE Tag Team Championship.
Photo: WWE
8. Stone Cold Steve Austin vs The Rock (WrestleMania 17)
In a showdown between two of the most popular wrestlers ever, it was Stone Cold--with the help of his former nemesis Vince McMahon--who defeated the People’s Champion after the two used each other’s finishers a multitude of times. The shock of Austin turning heel only added to the drama of this epic bout.
Result: Austin defeated The Rock for the WWF Championship.
Photo: WWE
7. Hulk Hogan vs Andre the Giant (WrestleMania 3)
It wasn’t the most technically skilled wrestling tilt ever, but that doesn’t matter when it comes to a match this entertaining. Andre the Giant entered the ring by stepping over the top ropes, but the Eighth Wonder of the World found himself on the wrong end of an iconic slam delivered by Hogan, ending Andre the Giant’s 15-year undefeated streak.
Result: Hogan defeated Andre the Giant to retain the WWF World Heavyweight Championship.
Photo: WWE
6. The Undertaker vs Mankind (King Of The Ring, 1998)
In one of the most discussed fights of all time, the Undertaker brutally beat Mankind in and out of the ring. The most iconic moment came when the Phenom threw Mankind off the top of the cell into the announcer’s table.
Result: Undertaker defeated Mankind.
Photo: WWE
5. Bret Hart vs Stone Cold Steve Austin (WrestleMania 13)
With Ken Shamrock as the special guest referee, Hart used his signature Sharpshooter leg lock, causing Austin to pass out from pain and loss of blood. After the hard-fought battle, Hart turned heel while Austin became one of wrestling’s biggest stars.
Result: Hart defeated Austin by submission.
Photo: WWE
4. Shawn Michaels vs Bret Hart (Survivor Series, 1997)
In his last match with the WWF before departing for the WCW, Hart lost the World Heavyweight title to Michaels after Vince McMahon decided to award the title to the Heartbreak Kid without the Hitman's knowledge. It's notoriously known as "The Montreal Screwjob."
Result: Michaels defeated Hart by submission to win the WWF World Heavyweight Championship.
Photo: WWE
3. Shawn Michaels vs Razor Ramon (WrestleMania X)
In absolutely stacked card, the Michaels-Ramon Ladder Match stood out above the rest. The battle had a multitude of epic moments, such as HBK's iconic splash from the ladder. In the end, Ramon came away victorious after Michaels got tangled in the ropes.
The bout was voted the Match of the Year by Wrestling Observer Newsletter in 1994.
Result: Ramon defeated Michaels in a Ladder Match to retain the WWF Intercontinental Championship.
Photo: WWE
2. Randy Savage vs Ricky Steamboat (WrestleMania III)
While the Andre the Giant versus Hulk Hogan match stole the headlines, it was the battle for the Intercontinental Championship that truly excited fans. Savage and Steamboat went back and forth at a frantic pace, with Steamboat eventually using the small package move to steal a victory--fand the Intercontinental title.
Result: Steamboat defeated Savage for WWF Intercontinental Championship.
Photo: WWE
1. Shawn Michaels vs Undertaker (WrestleMania 25)
At WrestleMania 25, the Heartbreak Kid and the Phenom put on the best match in WWE history. ‘Taker escaped with a victory after catching Michaels with a Tombstone Piledriver to extend his WrestleMania streak to 17 consecutive victories. The battle was named the Match of the Year in 2009 by the WWE Slammy Awards, Pro Wrestling Illustrated and the Wrestling Observer Newsletter.
Result: Undertaker defeated Michaels.
Photo: WWE
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