Shawn Michaels' 5 Best WWE WrestleMania Matches

Sid Pullar III | Oct 17, 2024

IMAGO / Zuma Press Wire

There might not be another pro wrestling star as synonymous with an event quite like Shawn Michaels is to WrestleMania. WWE's premier pay-per-view event has been a stage for many all-time greats to showcase their abilities and star power, such as Hulk Hogan, The Undertaker and Stone Cold Steve Austin. However, only one man earned the moniker of "Mr. WrestleMania." Over the course of two decades, "The Heartbreak Kid" showed why he is widely regarded as the greatest in-ring performer of all time on the Grandest Stage of Them All. Here are the five best WWE WrestleMania matches of Shawn Michaels' career.

5. Shawn Michaels vs. The Undertaker (Career vs. Streak) - WrestleMania 26

Starting with the match that capped his legendary career, WrestleMania 26 was headlined by Shawn Michaels facing The Undertaker in a rematch from their incredible contest the year prior. The two legends put on a masterful buildup with Michaels being obsessed with avenging his loss at WrestleMania 25 and costing Taker his World Heavyweight Title.

This match was so important to Michaels that he put his career on the line to end Undertaker's undefeated streak at Mania. This 24-minute battle had the Phoenix crowd fully invested and enthralled with every big spot and nearfall. The fans knew they were either going to witness the end of an icon's career or the most vaunted streak finally vanquished. In the end, it was Taker who came out on top with Michaels going out on his shield at the end of this epic encounter.

4. Shawn Michaels vs. Triple H vs. Chris Benoit - WrestleMania 20

WWE.com

By the time Shawn Michaels got to WrestleMania 20, he had fully refound his groove after his four-year retirement and was knee-deep in his fierce rivalry with Triple H. The main event saw the two men in the same ring as Chris Benoit, who was looking to complete his near 20-year odyssey to finally win the World Heavyweight Championship for the first time.

These three legends put on an outstanding 24-minute belter that blended intense in-ring action with brilliant storytelling. The story saw Michaels and Triple H working together to take out Benoit and settle their score one-on-one, only for "The Canadian Crippler" to come back and come out victorious. This made for one of the most compelling WrestleMania main events ever and arguably the very best triple threat in WWE history.

3. Shawn Michaels vs. Razor Ramon (Ladder Match) - WrestleMania 10

Introducing a new match concept is one of the biggest challenges a pro wrestler can face. That is exactly what the obstacle wa for Shawn Michaels and Razor Ramon when they fought to determine the Undisputed WWE Intercontinental Champion in a Ladder Match at WrestleMania X.

The first televised ladder match featured Michaels putting on an amazing performance that showcased his innovation in fascinating ways. HBK inflicted damage with the ladder in various matters and even flew off the 10-foot high object to deliver a highlight that is still shown in WrestleMania video packages years later. This stands as Ramon's best match of his career and set the standard for what would become an iconic stipulation for the company to this day.

2. Shawn Michaels vs. Kurt Angle - WrestleMania 21

Shawn Michaels and Kurt Angle are considered two of the greatest in-ring performers of their generation. At WrestleMania 21, the two men met in the squared circle for the first time. After an entertaining build with Angle playing mind games with Michaels, their encounter was one of the most highly anticipated matches on the Show of Shows.

This 27-minute bout displayed Angle's superb technical wrestling skills and HBK's intricate storytelling abilities. From high risk spots to ringside to splendid sequences, this match had everything a fan could look and was an in-ring masterclass. Michaels and Angle had immediate chemistry with one another and had every fan in the Staples Center on the edge of their seat. Many fans regard this match as high on the list of both men's most memorable bouts of their legendary careers.

1. Shawn Michaels vs. The Undertaker - WrestleMania 25

While their WrestleMania 26 main event is fondly remembered, Shawn Michaels vs. The Undertaker at WrestleMania 25 is still the superior match and one that has been talked about all these years later. From the heaven vs. hell entrances to the big fight feel from the opening bell, the two legends had the fans in the Houston Astrodome eating out of their palms before they even locked up.

This instant classic took every fan on a rollercoaster ride of emotions. Filled with spellbinding drama and tremendous chemistry throughout, HBK and Taker showed why they are often mentioned among the best WrestleMania performers in the event's history. Mr. WrestleMania vs. The Streak told an unbelievable story that had excellent nearfalls and facial expressions that have been replayed almost two decades later. It is a timeless battle that set the stage for a four-year story across the next three Manias. When you ask a fan for the greatest WrestleMania match ever, this is often one of the first bouts mentioned.

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