10 Things You Didn't Know About Shawn Michaels

4. Most ‘Match Of The Year’ Awards

shawn michaels sunny
WWE.com

Pro Wrestling Illustrated is seen by many as the most important wrestling outlet available, and as such their annual awards are recognised as the measuring stick by fans, critics and wrestlers alike.

Shawn Michaels is the proud holder of the most PWI Match of the Year Awards since the prize began back in 1972, having won the award a whopping eleven times.

The matches of the Heartbreak Kid’s that won said awards are as follows:

1993: vs Marty Jannetty – Monday Night Raw

1994: vs Razor Ramon – Wrestlemania 10

1995: vs Diesel – Wrestlemania 11

1996: vs Bret Hart – Wrestlemania 12

2004: vs Triple H vs Chris Benoit – Wrestlemania 20

2005: vs Kurt Angle – Wrestlemania 21

2006: vs Vince McMahon – Wrestlemania 22

2007: vs John Cena – Monday Night Raw

2008: vs Ric Flair – Wrestlemania 24

2009: vs The Undertaker – Wrestlemania 25

2010: vs The Undertaker – Wrestlemania 26

Not only do these awards back up why Shawn is regarded as one of the very best to ever lace up a pair of boots, the amount of these award-winning matches that took place at the Showcase of the Immortals gives further evidence as to why Shawn Michaels is known as Mr. Wrestlemania.

Senior Writer
Senior Writer

Once described as the Swiss Army Knife of WhatCulture, Andrew can usually be found writing, editing, or presenting on a wide range of topics. As a lifelong wrestling fan, horror obsessive, and comic book nerd, he's been covering those topics professionally as far back as 2010. In addition to his current WhatCulture role of Senior Content Producer, Andrew previously spent nearly a decade as Online Editor and Lead Writer for the world's longest-running genre publication, Starburst Magazine, and his work has also been featured on BBC, TechRadar, Tom's Guide, WhatToWatch, Sportkskeeda, and various other outlets, in addition to being a Rotten Tomatoes-approved film critic. Between his main day job, his role as the lead panel host of Wales Comic Con, and his gig as a pre-match host for Wrexham AFC games, Andrew has also carried out a hugely varied amount of interviews, from the likes of Robert Englund, Kane Hodder, Adrienne Barbeau, Rob Zombie, Katharine Isabelle, Leigh Whannell, Bruce Campbell, and Tony Todd, to Kevin Smith, Ron Perlman, Elijah Wood, Giancarlo Esposito, Simon Pegg, Charlie Cox, the Russo Brothers, and Brian Blessed, to Kevin Conroy, Paul Dini, Tara Strong, Will Friedle, Burt Ward, Andrea Romano, Frank Miller, and Rob Liefeld, to Bret Hart, Sting, Mick Foley, Ricky Starks, Jamie Hayer, Britt Baker, Eric Bischoff, and William Regal, to Mickey Thomas, Joey Jones, Phil Parkinson, Brian Flynn, Denis Smith, Gary Bennett, Karl Connolly, and Bryan Robson - and that's just the tip of an ever-expanding iceberg. Where his beloved Wrexham AFC is concerned, Andrew is co-host of the Fearless in Devotion podcast, which won the Club Podcast of the Year gong at the 2024 FSA Awards.