The Undertaker and Shawn Michaels split their singles series 2–2, and they did it in two separate eras. In 1997 and 1998 they wrestled the first-ever Hell in a Cell match and a casket match that ended Michaels' full-time career for four years. In 2009 and 2010 they met at back-to-back WrestleManias in matches that are still regularly called the best in the event's history, the second of which retired Michaels.
This page covers all five of their big singles meetings, the backstory in both eras, a comparison of the two careers, how fans and critics received the WrestleMania matches and our verdict.
Head-to-head record
The Undertaker vs. Shawn Michaels: 2–2 (1 no contest). Every big-event meeting between the two, oldest first.
| # | Date | Event | Venue | Match | Result | How |
|---|---|---|---|---|---|---|
| 1 | Sep 7, 1997 | Ground Zero: In Your House | Louisville Gardens, Louisville, Kentucky | Singles | No contest | Both men attacked the referees |
| 2 | Oct 5, 1997 | Badd Blood: In Your House | Kiel Center, St. Louis | Hell in a Cell (the first) | Shawn Michaels won | Kane's debut, then a pin |
| 3 | Jan 18, 1998 | Royal Rumble 1998 | San Jose Arena, San Jose, California | Casket match · WWF Championship | Shawn Michaels won | Kane-led interference |
| 4 | Apr 5, 2009 | WrestleMania 25 | Reliant Stadium, Houston | Singles (The Undertaker's Streak) | The Undertaker won | Tombstone Piledriver |
| 5 | Mar 28, 2010 | WrestleMania XXVI | University of Phoenix Stadium, Glendale, Arizona | Streak vs. Career | The Undertaker won | Jumping Tombstone |
Every match: our commentary
Ground Zero: In Your House · Sep 7, 1997
Michaels had cost The Undertaker the WWF Championship at SummerSlam a month earlier by hitting him with a chair as special referee. Their first singles match was a wild brawl that went through the crowd and ended when officials could no longer control it. The no contest set up a match with a roof on it.
Badd Blood: In Your House · Oct 5, 1997
The first Hell in a Cell match ever was a showcase for both men, highlighted by Michaels being thrown off the side of the cage. With The Undertaker in control, the lights went out and his storyline brother Kane debuted, ripped the cage door off and hit The Undertaker with his own Tombstone. Michaels crawled over for the pin.
Royal Rumble 1998 · Jan 18, 1998
Michaels retained the WWF title when Kane and a group of other wrestlers attacked The Undertaker and closed him in the casket. Michaels landed back-first on the edge of the casket during the match, an injury that ended his full-time career after WrestleMania XIV two months later.
WrestleMania 25 · Apr 5, 2009
Michaels came out dressed in white as 'the light' to The Undertaker's darkness. The match went back and forth for half an hour with false finishes the crowd believed, including The Undertaker missing a dive to the floor and nearly being counted out. After a Sweet Chin Music and a Tombstone were both kicked out of, The Undertaker hit a jumping Tombstone to go 17–0.
WrestleMania XXVI · Mar 28, 2010
Michaels insisted on the rematch and put his career on the line. In the closing moments he slapped The Undertaker and dared him to finish it, and The Undertaker obliged with a jumping Tombstone. Michaels retired, giving his farewell speech on Raw the next night. The Streak moved to 18–0.
The backstory
The first era was built on a grudge: Michaels, as guest referee at SummerSlam 1997, swung a chair at The Undertaker, missed and hit him, costing The Undertaker the title. The Undertaker spent the autumn chasing Michaels, and the Hell in a Cell structure was created to keep Michaels from escaping.
The second era was about the Streak. Michaels had been the one great match-up The Undertaker had never had at WrestleMania, and he framed it as the one thing left on his list. When he lost in 2009 he spent a year asking for a rematch and finally put his career up to get it.
Tale of the tape
| The Undertaker | Shawn Michaels | |
|---|---|---|
| Billed height / weight | 6 ft 10 in · 309 lb | 6 ft 1 in · 225 lb |
| WWF debut | November 1990 | 1988 (The Rockers) |
| World titles in WWE | 7 | 4 |
| Royal Rumble wins | 1 (2007) | 2 (1995, 1996) |
| Signature finish | Tombstone Piledriver | Sweet Chin Music |
| Hall of Fame | Class of 2022 | Class of 2011 (and 2019 with DX) |
By the numbers
| Head-to-head stat | The Undertaker | Shawn Michaels |
|---|---|---|
| Singles wins vs. each other | 2 | 2 |
| WrestleMania record vs. each other | 2–0 | 0–2 |
| Wins with outside help | 0 | 2 (both via Kane) |
| Matches that ended a career | 1 (WrestleMania XXVI) | — |
How fans and critics reacted
Both WrestleMania matches were named Pro Wrestling Illustrated's Match of the Year, in 2009 and 2010, and WrestleMania 25 in particular is a fixture at the top of lists of the best WrestleMania matches ever.
The 1997 Hell in a Cell is remembered as the match that made the structure a WWE institution, and Kane's debut in it is one of the great surprise entrances in company history.
Our take
On paper it is 2–2, but the record flatters Michaels: both of his wins came through Kane's interference, while The Undertaker won both WrestleMania matches clean. We give the rivalry to The Undertaker.
If you only watch one, watch WrestleMania 25. It is the best example of two veterans using the crowd's belief in the Streak to make every near-fall feel like the end.
Our verdict: The Undertaker.
FAQ
Who won the first Hell in a Cell match?
Shawn Michaels beat The Undertaker at Badd Blood on October 5, 1997, after Kane made his WWF debut and attacked The Undertaker.
Did The Undertaker retire Shawn Michaels?
Yes. Michaels lost a Streak vs. Career match at WrestleMania XXVI on March 28, 2010 and retired.
What is the head-to-head record?
2–2 in singles matches on big events, plus a no contest at Ground Zero in 1997.
More rivalries
Sources: Wikipedia: Badd Blood: In Your House · Wikipedia: Royal Rumble (1998) · Wikipedia: WrestleMania 25 · Wikipedia: WrestleMania XXVI. Facts verified Oct 18, 2026.