Shawn Michaels and The Undertaker go down in WWE history as two of the best wrestlers to ever compete in the business. They were also two of the last remaining wrestlers from the first episode of Monday Night Raw to ride off into the sunset, although Undertaker did it a full decade after HBK.
Through the almost 20 years they spent together in WWE, these legends only wrestled against each other on limited occasions, but every time they fought, it meant something. Without further ado, here is a look back at the 10 best Undertaker vs. Shawn Michaels matches, ranked.
10 CROWN JEWEL 2018
When Shawn Michaels retired in 2010, he promised that was the end and it was for almost a decade. Fans wanted him to come back for "one more match" against Daniel Bryan and other wrestlers, and he rejected it every time. However, when WWE wanted to please Saudi Arabia by bringing back legends, he finally gave in and came back for a match with DX fighting The Brothers of Destruction.
Forget the strange visuals of a bald Michaels. It was just all around a bad match, with several botches, and Triple H suffering yet another injury mid-match. Michaels looked better than the other three, but he should have stayed retired.
9 RAW (3.26.07)
Shawn Michaels and Undertaker faced off three times on free TV. The worst of the three matches came in 2007. Michaels was at the top of his game here, rejuvenated, wrestling smarter than ever, and turning in good matches against almost anyone. However, this was a tag team match that was more angle than a match.
Michaels teamed with John Cena to fight Undertaker and Batista. At WrestleMania, Undertaker was set to battle Batista and Michaels took on Cena. That meant no one could trust anyone. Undertaker walked out on the match, and Michaels turned on Cena, allowing Batista to pick up the win.
8 RAW (8.18.97)
The one match between Shawn Michaels and Undertaker on free TV during the Attitude Era took place on Monday Night Raw in August 1997. At this time, Degeneration X was not yet in power, and Michaels was forced to team with Triple H to fight Undertaker and Mankind before the two men fought at In Your House: Ground Zero.
The match ended when Michaels bashed Undertaker with a steel chair, causing the DQ. This came after "Ravishing" Rick Rude showed up as insurance, distracting Undertaker. HBK then bloodied Taker with a chair before running off. This was all part of the genesis of Degeneration X.
7 RAW (11.16.09)
This was the third and last time that Shawn Michaels and Undertaker battled on free television. Fans were treated to a triple threat tag team match that saw Undertaker teaming up with John Cena to fight D-Generation X and JeriShow (Chris Jericho and Big Show).
The deal here is that Cena and Undertaker are the two world champions. At Survivor Series, Cena will defend his title against Triple H and Shawn Michaels in a triple threat match. The match saw everyone hitting their finishing moves and Cena pinning Triple H.
6 ROYAL RUMBLE 1998
This was the match that almost ended Shawn Michaels' career. HBK was the WWE Champion at this time, and he defended his title against The Undertaker in a Casket Match, which took place as the main event after Stone Cold Steve Austin won his second Royal Rumble in a row.
For those who don't know, Undertaker backdropped Michaels over the casket. HBK landed with his back on the edge, and that is what forced him into temporary retirement after he lost the title to Austin at WrestleMania three months later. HBK won this match when Kane came down and slammed Undertaker into the casket before lighting it on fire.
5 NO WAY OUT 2007
The Undertaker and Shawn Michaels battled at No Way Out 2007 in a tag team match, featuring Cena teaming with HBK, and Batista teaming with 'Taker. What makes this one rank higher is that the match was a main event quality match and had little shenanigans.
In their tag match on Raw, Michaels turned on Cena, and Undertaker walked out on Batista. In this one, the two teams fought for 22 minutes, and while it still ended in a double-cross when Batista turned on Undertaker, it was great up to that point. HBK hit Sweet Chin Music on Taker, and Cena hit the FU for the win.
4 IN YOUR HOUSE 17 (Ground Zero)
WWE In Your House 17 was titled Ground Zero, and this is the PPV that followed the Monday Night Raw in August 1997 where Michaels bloodied Undertaker with a chair and started the formation of D-Generation X.
Michaels played the chicken heel perfectly here, trying to run away at the start, but forced back to the ring by Commissioner Sgt. Slaughter. Triple H, Chyna, and Rick Rude came out to help Michaels, further solidifying their partnership. The biggest problem here is that the match ended in a No Contest when Undertaker started taking out referees. However, for 16 minutes, these guys tore down the house.
3 IN YOUR HOUSE 18 (Badd Blood)
After the no contest and the constant interference at Ground Zero, WWE decided a new match needed to take place between Undertaker and Shawn Michaels. Yes, this was the first-ever Hell in a Cell match, and it remains one of the best Hell in a Cell matches of all-time.
The match does not have all the high spots that came in later Hell in a Cell fights, but it had some of the best ring psychology of any of them. Plus, this was the match that ended when Kane made his WWE debut, tore the door off the cage, and attacked his brother, helping HBK win.
2 WRESTLEMANIA XXV
This was the first of the back-to-back Shawn Michaels vs. Undertaker matches at WrestleMania that would eventually end the career of HBK. Michael's entrance was amazing as he descended from the ceiling, dressed all in white, while Undertaker came in with his usual entrance, dressed all in black.
The two then went out and delivered what might be the greatest WrestleMania match of all-time, fighting for 30 minutes before Undertaker hit the Tombstone for the win.
1 WRESTLEMANIA XXVI
In his biography, Shawn Michaels said that he considered retiring after WrestleMania XXV. He felt that he couldn't have another match of the quality of that encounter with The Undertaker. However, WWE convinced Michaels to return for one more year and one more important story.
This ended up being a retirement match. If Michaels lost, he would have to retire from WWE, and he promised if he lost it would be for good. The match was shorter, but the emotion here makes it their very best encounter. The two men gave all they had, and Undertaker won to retire HBK.