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Wrestlemania Countdown: Undertaker vs Shawn Michaels I

Shawn Michaels and the Undertaker square off at WrestleMania 25
Photo Credit: TJR Wrestling

The wrestling staff of Back Sports Page have carefully selected what they believe to be the top 41 matches in WrestleMania history. Presented in chronological order, this series will detail the backstory, match review, and aftermath of each match, along with how the outcomes shaped the careers of those involved.

Backstory:

WrestleMania 25, held on April 5, 2009, at Reliant Field in Houston, Texas, featured two veterans putting everything on the line to deliver an instant classic match. The Undertaker and Shawn Michaels faced off in a match where the central themes were darkness versus light and legacy versus immortality. Both stars had strong reputations entering this match. Shawn earned the nickname ‘Mr. WrestleMania’ by delivering classic matches year after year. As for The Phenom, he had a legendary undefeated WrestleMania streak, which stood at 16-0.

At the time, both men were on the SmackDown brand as part of the build-up. The Undertaker solidified himself as one of SmackDown’s cornerstones, dominating the brand and capturing multiple World Heavyweight Championships. Shawn Michaels, though mainly on Raw, began appearing on SmackDown with Triple H as part of D-Generation X.

The build-up was intense. Both men went back and forth with weeks of mind games and fierce promos. It did not disappoint. Not to mention, this isn’t the first time both men have crossed paths. Their rivalry began in 1997 with the infamous Hell in a Cell match at Bad Blood.

Match Review:

You can argue that this match is the greatest of all time. Both men gave everything to ensure this match would be an instant classic. The match did kick off slowly, but as it progressed, it turned into a physical fight.  Both competitors had showcased their trademark moves. Shawn Michaels displayed his incredible agility with a moonsault from the top rope to the outside. In a surprising turn, Undertaker responded with a suicide dive that left the crowd in awe. Additionally, these two moves were what made this match so great.

As the match came close to conclusion, drama intensified. Both men exchanged finishing moves, with Shawn kicking out of a devastating tombstone piledriver and Undertaker surviving Sweet Chin Music. The crowd was left in shock, unsure who would come out victorious. Ultimately, the phenom would be the last one standing as victorious. All it took was one last tombstone piledriver to put the Heart Break Kid away. This win also extended the Undertaker’s undefeated streak to 17-0. As for Shawn, he would be left feeling disappointed in himself after falling short.

Aftermath:

  • Undertaker‘s win at WrestleMania would arguably go down as the greatest match he has ever fought during his 30-year career. Unfortunately, he would have to take some time due to injuries he sustained during the match, but he later returned stronger. He eventually won the World Heavyweight Championship again in Hell in a Cell by defeating CM Punk. His reign led to a feud with Batista and Chris Jericho. Most notably, it built toward a rematch with Shawn at WrestleMania the following year.
  • Shawn Michaels would reunite with his best friend Triple H in their quest to become tag team champions. It would turn out to be his final championship. However, Shawn would still be distracted by his loss to the Undertaker in the 25th anniversary of WrestleMania. His rivalry with the Deadman would begin again until the Elimination Chamber after costing Taker his chance of retaining the title.
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