Shawn Michaels and The Undertaker had one of the best rivalries in WWE history. The two legends worked together at different points in their careers, creating moments fans will never forget. Michaels and Undertaker made the Hell in a Cell match relevant in the late '90s and had their iconic WrestleMania matches over a decade later.
However, there were forgotten moments that deserve more love when looking back at their work together. Michaels and Undertaker had tremendous chemistry that produced good content, more than the average pairing in a feud. Find out more than just the highlights fans see often in WWE productions, when it comes great moments between Michaels and Undertaker that most fans forget about.
10 Match That Set Up Hell In A Cell Concept
The feud between Shawn Michaels and The Undertaker in late 1997 started their string of great matches throughout the years. WWE ran a surprising finish to their PPV main event at the In Your House: Ground Zero event.
The no contest ending set up the following month’s event, with the debut of the Hell in a Cell match. Michaels and Undertaker had a strong match until the ending, which saw both men using weapons and hitting referees. WWE ran one of their first segments of the locker room coming out to separate them, which felt like a big deal at the time.
9 Undertaker's 2018 Promo Calling Out Michaels Coming Out Of Retirement
WWE clearly wanted to make the most out of their big budget for Saudi Arabia events, when convincing Shawn Michaels to come out of retirement in 2018. The big match of DX vs. the Brothers of Destruction was an embarrassment, but there was a strong promo by Undertaker, months before to set it up.
Michaels was showing his support for Triple H when he was having a singles match with Undertaker. The interruption from Undertaker claimed Michaels was more afraid of facing Undertaker, as opposed to honoring their prior match stipulation that forced his retirement.
8 Michaels Impersonating Undertaker
The end of the 1997-1998 feud for Shawn Michaels and The Undertaker came at Royal Rumble 1998 in a casket match. Michaels won when Kane betrayed Undertaker to move forward with that feud, in the early months of the Brothers of Destruction rivalry.
Kane trapping Undertaker in a casket and setting it on fire took Undertaker off television for a few weeks. Michaels tricked fans into thinking Undertaker was coming to the ring the following night by dressing as him for the legendary entrance. The hilarious reveal saw Michaels taking off his wig and hat to dance in the ring for heel heat.
7 Undertaker & Batista Vs. Michaels & John Cena Matches
WWE decided to use the two major title matches at WrestleMania 23 as part of a story of the opponents teaming up against each other. Batista and The Undertaker represented Smackdown against Raw’s Shawn Michaels and John Cena on two occasions.
Both matches ended up being quite compelling, with the storytelling delivering each time. The two bouts had similar endings of partners turning on each other, but fans loved the limited interactions that saw Undertaker and Michaels mixing it up.
6 Kane Saving Undertaker Vs. DX
The 1998 rivalry between The Undertaker and Shawn Michaels featured a great story with a fake out. Kane made the save for Undertaker on Raw, a few weeks before the big casket match. Michaels and the rest of DX delivered a group attack on Undertaker, until the shocking appearance of Kane.
Fans loved the moment of Kane showing face tendencies for the first time, getting physical with Michaels and Triple H to help his brother. The pop for Undertaker and Kane, each delivering their pose in the ring with the lights going off was a huge success.
5 Undertaker's Promo Demanding HBK Put His Career On The Line
WWE running the Shawn Michaels vs. Undertaker match at both WrestleMania 25 and WrestleMania 26 featured a big change in the second year’s story. Undertaker refused to wrestle Michaels, believing he had nothing left to prove.
Michaels cost Undertaker the World Championship to fuel his rage and get the match confirmed. Undertaker did agree, but cut a great promo demanding Michaels put his career on the line against his streak in the match. The promo showed more depth from Undertaker, instead of him just lashing out.
4 Michaels' White Outfit Parodying Undertaker's Entrance
The interest in the WrestleMania 25 match between The Undertaker and Shawn Michaels grew each week during a strong build. One segment stood out, when Michaels parodied Undertaker’s entrance during an episode of SmackDown.
The incredible reveal featured Michaels wearing all white, claiming to represent the power of light against Undertaker’s darkness and all-black gear. Michaels mocked Undertaker with a dance in the ring before Undertaker appeared from under the ring to attack. Their match became the biggest attraction for WrestleMania 25 after this moment.
3 Undertaker Proving Michaels Didn't Believe In Triple H At WrestleMania XXVIII
The retirement for Shawn Michaels led to Triple H stepping up next as the wrestler to challenge The Undertaker’s Streak at WrestleMania XXVII and WrestleMania XXVIII. WWE created a huge spectacle for the second match, with the Hell in a Cell stipulation and Michaels as the guest referee.
All three wrestlers sold the match during an incredible promo segment that featured Michaels almost losing his cool and seeing his superkick stopped by Undertaker. The aftermath was even better when Triple H looked to Shawn to back him up in his quest to end the streak. Michaels was silent and left in the ring, showing that he knew the power of the streak was too great to end.
2 Michaels Costing Undertaker The Title Vs. Bret Hart
The first incredible moment involving The Undertaker and Shawn Michaels becoming enemies has been lost in translation throughout the years. Michaels was the guest referee for Undertaker’s WWE Championship match at SummerSlam 1997 against Bret Hart.
The issues between Hart and Michaels were the main story, with Bret getting in Shawn’s face to infuriate him. Michaels swung a chair at Hart who ducked, leading to Undertaker getting hit. The role of referee forced Shawn to make the count for Bret’s win, which caused Undertaker to target Michaels moving forward.
1 Royal Rumble 2007 Ending
WWE decided to role with the star power of their active legends in 2007 when Shawn Michaels and The Undertaker were both world title contenders on their respective shows. The Royal Rumble match that year would see their iconic performance as the final two.
Undertaker and Michaels had one of the longest endings to a Rumble, going back and forth like an actual match. Fans were invested in every second until Undertaker finally eliminated Michaels to win a World Championship match at WrestleMania 23.