10 Final Matches Of His Career Ranked From Worst To Best

Shawn Michaels is arguably the greatest wrestler of all time, and that was the case right up until his retirement from the sport. He was consistent with his performances, always bringing fantastic matches to the table, and towards the end of his career, he really had an amazing run.

The Heartbreak Kid feuding to try and face The Undertaker one final time led to some great moments in terms of storytelling and matches. His final bouts in WWE were incredibly varied, from tag team matches to singles bouts on PPV and on Raw and SmackDown, but which of the 10 were the biggest standout matches?

10 D-Generation X Vs Big Show & The Miz (March 1, 2010)

These two teams were capable of great matches and while this match wasn't bad, it also wasn't great. The main issue with it was the fact it only lasted for just over four minutes, so everything had to be crammed into a short space.

However, they really did make the most of the time they had in the ring, with HBK, in particular, getting the fans going. However, a distraction from The Undertaker ended up costing DX this match, with this mainly being used to build their feud.

9 Shawn Michaels Vs Chris Jericho (March 15, 2010)

Shawn Michaels and Chris Jericho have a long history against each other, and they've had some classic matches during that period. This match on Raw was the last time they competed in a match where both men were showing major aggression.

It was done mainly to build towards WrestleMania, but in order not to make Jericho look weak heading in as champion, he walked away from this match resulting in a count-out, meaning that they didn't get a true conclusion.

8 Shawn Michaels Vs Kane (March 22, 2010)

This was Shawn Michaels' final match on Monday Night Raw, and it was done as a last build towards his match with The Undertaker. The Deadman showed up partway through, but that wasn't enough to make the difference.

The match was technically no disqualification, but that was only so Undertaker could pop up. It was a straightforward match with Michaels trying to chop the bigger man down, and it was effective for what it was.

7 D-Generation X Vs Brothers Of Destruction (Crown Jewel 2018)

To put it simply, this match was a disaster. Everything that could have gone wrong went wrong, with Triple H being injured, Kane's mask falling off and Shawn Michaels missing a huge moonsault to the outside which was a really dangerous bump.

While seeing Michaels return is what fans wanted, this is not the way people hoped it would happen. The match was just incredibly sluggish and messy, but with nearly 30 minutes in the ring, there were some bright moments.

6 D-Generation X Vs Legacy (January 25, 2020)

This Monday Night Raw match was all about the tension between Shawn Michaels and Triple H as the build to the Royal Rumble began. Both men wanted to win the match and they certainly weren't on the same page, with Michaels tagging himself in just as Triple H was about to win the match.

Despite the tension, the experienced tag team did manage to come out on top. Shawn Michaels himself put in an impressive performance here, going over the top as the underdog babyface being beaten down for large parts of the match, making the young team look great.

5 Shawn Michaels Vs Randy Orton (February 1, 2010)

Despite the fact that this Raw match only lasted just over six minutes, Shawn Michaels and Randy Orton managed to make this really entertaining. While it started slowly, they quickly picked things up by throwing in some major moves to get the audience to buy into near falls early on.

This was an Elimination Chamber qualifier and Michaels was very desperate at this point. He was set to win, kicking up and getting ready to hit the Sweet Chin Music, but Orton ended up rolling him up for the win in what was a really unique finish that people didn't see coming.

4 DX Vs Straight Edge Society Vs ShowMiz (February 8, 2010)

This was a really fun tag team elimination match on Monday Night Raw for the Unified Tag Team Titles. Because it had all three teams legal, there was plenty of action going on here and it allowed for a lot of excitement.

Shawn Michaels managed to pin CM Punk to eliminate The Straight Edge Society. But when it came down to D-Generation X against Big Show and The Miz, the match really picked up. ShowMiz ended up winning here and they really worked well as heels, with the fans buying into the full match.

3 Shawn Michaels Vs Rey Mysterio (January 29, 2010)

This match was Shawn Michaels' final match ever on the blue brand and it was an absolutely fantastic way to bow out as far as his SmackDown career was considered. HBK and Rey Mysterio had brilliant chemistry and they really put together a fantastic, fast-paced match.

This was back-and-forth contest with the momentum alternating between them throughout, with HBK catching Mysterio with a huge Sweet Chin Music off a springboard. But sadly, this didn't have a clean finish with Batista causing interference for a DQ.

2 Royal Rumble Match (Royal Rumble 2010)

This is one of the best Royal Rumble matches of all time, and Shawn Michaels played a huge part in that. The match was star-studded and featured some amazing names, but it was all about HBK within the match as he was desperately trying to win in order to face The Undertaker at WrestleMania.

That desperation was played out throughout the match as he clashed with his tag team partner, Triple H, as well as other major names. In the end, the match was won by a returning Edge which was an unforgettable moment, but it was Michaels who stole the show with his performance.

1 Shawn Michaels Vs The Undertaker (WrestleMania XXVI)

This is not only the best match from Shawn Michaels' final 10, but it is arguably the best match of his entire career. HBK and The Undertaker set the bar very high the previous year at WrestleMania, but somehow they managed to top it within this match.

With Michaels' career on the line, there was tons of emotion poured into the match from both men and it really added to things. The in-ring work from both men was superb and it created a WrestleMania match nobody will ever forget.

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