10 Best Shawn Michaels Matches of The 2000s

Shawn Michaels is arguably the greatest in-ring performer in the history of not just the WWE, but professional wrestling as a whole.

He has wrestled countless match of the year calibre performances and never failed to disappoint. It has been often said that Shawn Michaels is one of those wrestlers who could carry a broomstick to a great match, and that is probably true.

While Shawn had amazing run in the 90s, it was actually his 2002 - 2010 comeback that gave us the majority of the best matches of his career.

Shawn Michaels is now stepping out of retirement for the second time, and why not celebrate what will be another triumphant return by looking over the top 10 best Shawn Michaels matches of the 2000s?

Honorable Mentions: Shawn Michaels vs. Shelton Benjamin - RAW 2005, Shawn Michaels vs. Rey Mysterio - Smackdown 2005, Shawn Michaels vs. Chris Jericho - RAW 2003, Great American Bash & Unforgiven 2008, Shawn Michaels vs. Edge - RAW 2005 & 2007, Shawn Michaels vs. Triple H - RAW 2003 & Bad Blood 2004, Shawn Michaels vs. Chris Benoit - RAW 2004, Shawn Michaels vs. Triple H vs. Chris Benoit - Backlash 2004, Shawn Michaels vs. John Cena - WrestleMania 23, Shawn Michaels vs. Vince McMahon - WrestleMania 22

#10 Shawn Michaels vs. Hulk Hogan - SummerSlam 2005

This is now a pretty infamous match. It was a dream match that, while still a good watch, was still ruined by both men as it could have been so much more.

The story goes that WWE wanted to do at least two, maybe three matches between them. The second match was already planned for a few months later, a steel Cage match. The plan was for Hulk Hogan to go over at SummerSlam (which he did) and Shawn Michaels to win the cage.

And the day of the event, Hogan claimed to have upcoming minor surgeries that would keep him out of the ring for at least a year and thus scrap the matches.

Shawn Michaels in turn, now angry over not getting his win in a rematch, decided to hilariously oversell everything Hogan did to him in the match. While it was very funny to see, it still could have been so much better of both had just stuck to the original plan. However, it is still a good and fun match to see.

It wasn't until early 2018 that Shawn Michaels finally commented on his overselling in the match, claiming that he feels he didn't actually oversell anything, and that WWE asked him to be the heel Shawn Michaels of the 90's and ''that is how the heel 90's Shawn Michaels sold''. he also said no matter how anyone feels about Hogan today, it was an absolute honour to be in the ring with him.

#9 Shawn Michaels vs. Chris Jericho - WrestleMania XIX

Everyone knew this match was going to be good, but I don't think anyone expected it to be as phenomenal as it was. Shawn had to really prove himself in this one because not only was it going to be his first WrestleMania match in 5 years, but by this point, Michaels had been back in WWE and had had at least 6 or 7 televised matches.

But only two of those had been up to the 'Shawn Michaels' standard.

After a disappointing 3 Stages of Hell match with Triple H at Armageddon 2002, Michaels immediately entered a feud with Chris Jericho, but wouldn't have an official one-on-one match with him until WrestleMania, and boy was it worth almost 3 months of waiting.

The timing of everything was on point, we had near fall after near fall, a tremendous exchange of reversals, Jericho performing his very own Sweet Chin Music and a whole lot more!

#8 Shawn Michaels vs. Kurt Angle - Vengeance 2005

Shawn Michaels and Kurt Angle had an absolutely stunning encounter at WrestleMania 21 earlier in 2005. When Kurt was drafted over to RAW three months later, they reopened their feud and set up this rematch for the Vengeance pay-per-view.

Shawn Michaels vs. Kurt Angle II was outstanding. It wasn't as great as their clash at WrestleMania 21 but it almost was, almost. The action here was smooth, a great mix of styles, lots of drama and intensity and many different moments where it looked like it was going to end, but didn't. Michaels picked up the win when Angle jumped from the top rope, landing on some Sweet-Chin Music.

Shawn and Kurt would go onto have a 30 minute Iron Man on the RAW homecoming show as a rubber match, but it ended in a draw. As exciting as it was and one final match between them in January 2006, they couldn't hold a candle to WrestleMania 21 or this epic showdown

#7 Shawn Michaels vs. Ric Flair - WrestleMania XXIV

We all knew Ric Flair was lacing up his boots for the final time (just in WWE as it turned out), so the finish would be obvious. However, no one, and I mean no one expected it to be as fantastic as it was.

Ric Flair had some very good wrestling matches during his 2001 - 2008 WWE run with the likes of Triple H, The Undertaker, Edge, Randy Orton and more, but by the time 2008 rolled around, it seemed all his great performances had come and gone. It was hard to know what to expect going in, and although Shawn Michaels is arguably the greatest performer of all time, he had a really tough job in having even a barely decent match with Flair at Bad Blood 2003, so could he get a better performance out of him 5 years later? As it turned out, yes.

The match told a good story, Michaels missed a moonsault and crashed through a table, with classic Flair spots mixed in, some good exchanges and the incredible “I’m sorry…I love you” moment before the Sweet Chin Music that left fans and the performers with a very emotional moment.

#6 Shawn Michaels vs. Chris Jericho - No Mercy 2008

Shawn Michaels and Chris Jericho always had great chemistry together, whether it was from their early feuding days in 2003, or their year stealing feud of 2008. Everyone likes to look fondly back at their clash from WrestleMania XIX in 2003 as the best match between them, and as great as it was, this one still takes the cake.

Often mentioned by Chris Jericho himself as his favorite WWE match he has had, the World Championship Ladder match between Chris and Shawn from No Mercy 2008 is simply outstanding.

Certainly underrated when fans talk about WWE's greatest matches, this grueling match had all the drama and intensity in the world, several notable high risk and dangerous spots, including when they both went crashing through the announce table from the top of the ladder and just a lot of jaw dropping action.

It really is very easy to see why Chris Jericho looks back at this as his favorite WWE match ever.

#5 Shawn Michaels vs. John Cena - WWE RAW 2007

Shawn Michaels and then WWE Champion John Cena collided in the main event of WrestleMania 23 in 2007, and had a very exciting match. It was so good, many immediately thought that they couldn't top it in a rematch, but they were proven wrong just a few weeks later.

Coming from the April 23, 2007 episode of RAW from London, England, this was an epic encounter. While these two gave us a great match at WrestleMania 23, they topped it with an amazing performance that took up half of an entire episode of RAW, going just under an hour at 56 minutes.

Michaels and Cena gave us everything you could ever want out of a wrestling match, a long well timed effort featuring two of the best, technical wrestling, high spots, several near falls and as much intensity and drama as humanly possible. Shawn took the win with some Sweet-Chin Music.

#4 Shawn Michaels vs. Triple H - SummerSlam 2002

It's easy to say, no one ever had a better comeback match than Shawn Michaels at SummerSlam 2002. After 4 years away, with only one match wrestled during that time (outside of WWE), Shawn Michaels returned to the ring to battle his now former best friend Triple H in this stunning unsanctioned match.

The live crowd was super hot for this match as there was barely ever a moment in this near 30 minute match where they paused for a second to rest. We had a lot of back and forth action, one of the most drama filled matches in history of WWE, a lot of weapon use leading to blood, and Michaels giving a stunning cross body to Triple H through the table.

This was an all out war. Shawn took the win when he reversed an attempted Pedigree into a bridging pin for the win. Not only the greatest comeback match ever, but the greatest comeback ever.

#3 Shawn Michaels vs. Triple H vs. Chris Benoit - WrestleMania XX

This is a match that, for obvious reasons, isn't talked about very often today, but it is easily the best match of 2004, one of the best WrestleMania matches of all time and the best Triple Threat match ever.

Michaels, HHH and Chris Benoit told an amazing story here. Could Benoit win the big one? Would the two year long feud between Michaels and The Game finally end? These led to broken tables, unlikely team ups, suplex after suplex, excellent one-on-one and then three way exchanges, superkicks, headbutts, high flying manoeuvres, technical offense and a whole lot of blood. No one needed to help carry the other into a great performance, all three men earned their PWI Match of The Year award.

The trio would go on to have a rematch the following month at Backlash, which was almost as fantastic as this, but just a little short of it.

#2 Shawn Michaels vs. Kurt Angle - WrestleMania 21

A dream match that sky rocketed expectations

While WWE often don't capitalize on promoting dream matches, when they do, they can be incredible matches. The Rock vs John Cena, The Rock vs Goldberg, Shawn Michaels vs Hulk Hogan, The Rock vs Hogan, they were all great in their own way, but none as perfect as Shawn Michaels vs Kurt Angle from WrestleMania 21.

This was truly amazing, as the gifted wrestlers lived up to the hype and then some. This was true wrestling, and the drama was incredible, with more than a dozen near falls, several Angle Slams, suplexes everywhere, a Sweet Chin Music that nearly took Angle's teeth out and what may be the longest Ankle Lock ever to secure the big win for the deserving Olympian. Match of the night, match of the year, and arguably match of the decade.

#1 Shawn Michaels vs. The Undertaker - WrestleMania XXV

This match might just be the best wrestling match we will ever see. Having put on a 5-star classic once before, back in the first ever Hell in A Cell match at Bad Blood 1997, Shawn Michaels and The Undertaker managed to have an even better, more incredible match at WrestleMania 25.

Everyone knew Shawn was going to lose, especially since the match had a build up of only about two weeks, but during the match itself, you really believed it was possible Shawn could pull off a win. They kicked out of each other's finishing moves more than once, with perfect exchanges and reversals everywhere, an incredible dive from the ring by Taker and even some of the best frustrated facial expressions you will ever see in a match.

This match rightfully won several Match of The Year awards and even spawned a sequel, to be Shawn Michaels' final WWE match the following year.

There was no doubt in anyone's mind that after this match, no one else could go out in a 5-star match with Shawn Michaels other than The Undertaker. The WrestleMania 26 match between them was excellent, but this match at WrestleMania 25 was just perfect.

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