The Undertaker's Definitive Best WrestleMania Matches, Ranked
Mia Lopez
Published Mar 27, 2026
When one thinks of WrestleMania, The Undertaker is the name most fans associate with the Grandest Stage Of Them All. From his first 'Mania appearance all the way back in 1991 to his last in 2020, The Deadman faced the very best WWE had to offer in some of the greatest wrestling matches of all time.
When Did WWE Start Making A Big Deal Of Undertaker’s Undefeated Streak?
The Undertaker's undefeated streak was the highlight of WrestleMania for many years. But when exactly did WWE start making a big deal out of it?As everyone knows, The Undertaker slowly developed an impressive winning streak at WrestleMania. Regardless if it was planned or not, the fact is it eventually became a big deal as everyone wanted to see who'd challenge the Streak next. The following are Undertaker's definitive 10 best WrestleMania matches out of the whopping 27 bouts he wrestled at the event in his iconic career.
To learn more about how we rank wrestling matches on TheSportster, please check out our match ranking criteria guide here.
10 The Undertaker Vs. Triple H (WrestleMania 17)
Overall Rating From TheSportster: 7.25/10
Storytelling | 1.75/2.5 |
|---|---|
Technical Ability | 1.75/2.5 |
Character Work/Psychology | 1.5/2.5 |
Crowd Reaction | 2.25/2.5 |
- Dave Meltzer's Rating: 3.5 Stars
- Cagematch.net Rating: 7.91
Everyone remembers The Undertaker's epic rivalry with Triple H over the years. But for whatever reason, their matchup at WrestleMania 17 is often ignored by some fans and even the company. Their matches in the early 2010s are often brought up, yet WWE rarely mentions their first 'Mania encounter.
That's a shame as it was a pretty good match - despite the hilariously long ref bump - and it deserves more love. Triple H was on fire after having had a spectacular year in 2000 filled with awesome matches, and his battle with The American Badass at WrestleMania 17 was no exception.
9 The Undertaker Vs. Kane (WrestleMania 14)
Overall Rating From TheSportster: 7.75/10
Storytelling | 2.25/2.5 |
|---|---|
Technical Ability | 1.25/2.5 |
Character Work/Psychology | 2/2.5 |
Crowd Reaction | 2.25/2.5 |
- Dave Meltzer's Rating: 1.5 Stars
- Cagematch.net Rating: 7.19
If there was ever a feud that delivered in terms of storytelling and entertainment yet rarely delivered inside the ropes, it would be The Undertaker vs. Kane. Ever since Kane's epic debut at Badd Blood 1997, fans were excited to see the two brothers going at it. After months of anticipation, they finally met at WrestleMania 14.
While most of their matches were nothing special - particularly their battles in 2010 - 'Mania 14 was different. They had a dramatic bout with fans loving every second of it. Kane was able to kick out of two consecutive Tombstones, which had never been done before. However, a third one was able to put The Big Red Machine down for the three count.
8 The Undertaker Vs. Randy Orton (WrestleMania 21)
Overall Rating From TheSportster: 8/10
Storytelling | 2/2.5 |
|---|---|
Technical Ability | 1.75/2.5 |
Character Work/Psychology | 2/2.5 |
Crowd Reaction | 2.25/2.5 |
- Dave Meltzer's Rating: 3.5 Stars
- Cagematch.net Rating: 7.87
After leaving Evolution and becoming the youngest World Champion in WWE history, Randy Orton struggled as a babyface on the Raw roster. It didn’t take long for the company to figure it out and Orton became a heel again, going after The Undertaker’s Streak.
Why Randy Orton Regrets His Classic WrestleMania Match Vs. The Undertaker
Randy Orton had a bad attitude in the early days of his WWE career, and he even disrespected The Undertaker before their WrestleMania 21 match.The two men had a spectacular match at WrestleMania, and their feud only continued to grow after The Show Of Shows. Orton almost won after reversing the Chokeslam into the RKO, but ‘Taker kicked out. Undertaker eventually won with the Tombstone Piledriver.
7 The Undertaker Vs. Batista - World Heavyweight Championship (WrestleMania 23)
Overall Rating From TheSportster: 8.25/10
Storytelling | 2/2.5 |
|---|---|
Technical Ability | 1.75/2.5 |
Character Work/Psychology | 2.25/2.5 |
Crowd Reaction | 2.25/2.5 |
- Dave Meltzer's Rating: 4 Stars
- Cagematch.net Rating: 8.47
The Undertaker won the Royal Rumble Match for the first and only time in 2007. He began a feud with the World Heavyweight Champion Batista, challenging ‘The Animal’ for the title at WrestleMania 23. They exceeded everyone’s expectations that night, putting on a great heavyweight tussle.
Batista did everything to avoid the Tombstone, blocking it and hitting the Batista Bomb for the best nearfall of the match. A few moments later, The Deadman managed to deliver the Tombstone Piledriver and captured the Big Gold Belt for the first time in his career.
6 The Undertaker Vs. Triple H (WrestleMania 27)
Overall Rating From TheSportster: 8.75/10
Storytelling | 2.5/2.5 |
|---|---|
Technical Ability | 1.75/2.5 |
Character Work/Psychology | 2/2.5 |
Crowd Reaction | 2.5/2.5 |
- Dave Meltzer's Rating: 4.5 Stars
- Cagematch.net Rating: 8.48
Ten years after their aforementioned battle at WrestleMania 17, Triple H challenged Undertaker’s undefeated Streak yet again. This time The Game was more motivated than ever, with his best friend Shawn Michaels having been retired by ‘Taker the previous year.
Triple H gave it his all as he tried to be the one to finally end the Streak. The fight was so intense that Undertaker actually had to be carried out of the ring - a finish Vince McMahon reportedly hated and the first time ‘Taker wasn’t able to stand tall at the end of a WrestleMania battle. Despite that, Undertaker was still able to win after making Hunter tap out to his Hell’s Gate submission hold.
5 The Undertaker Vs. CM Punk (WrestleMania 29)
Overall Rating From TheSportster: 8.75/10
Storytelling | 2/2.5 |
|---|---|
Technical Ability | 2.25/2.5 |
Character Work/Psychology | 2.25/2.5 |
Crowd Reaction | 2.25/2.5 |
- Dave Meltzer's Rating: 4.5 Stars
- Cagematch.net Rating: 9.02
CM Punk had a fantastic 2012 with The Straight Edge Superstar holding the WWE Championship the entire year. After losing the title to The Rock at Royal Rumble 2013, Punk was determined to make even more history and he challenged Undertaker at WrestleMania 29.
Punk came close several times in what turned out to be The Deadman’s final win in the Streak. CM Punk delivered a great flying elbow drop onto the announce table, but the best spot was when Undertaker bounced off the ropes after getting hit with the GTS and immediately delivered the Tombstone. It was the best match on a rather weak show.
4 The Undertaker Vs. Edge - World Heavyweight Championship (WrestleMania 24)
Overall Rating From TheSportster: 9.25/10
Storytelling | 2.25/2.5 |
|---|---|
Technical Ability | 2.25/2.5 |
Character Work/Psychology | 2.5/2.5 |
Crowd Reaction | 2.25/2.5 |
- Dave Meltzer's Rating: 4.25 Stars
- Cagematch.net Rating: 8.91
Undertaker’s title reign in 2007 was cut short when Edge cashed in Money in the Bank on The Deadman in May. At Survivor Series, Undertaker lost to Batista inside Hell in a Cell thanks to the returning Edge’s interference and the Rated-R Superstar found a way to become World Champion again.
Undertaker won SmackDown’s Elimination Chamber at No Way Out 2008 and challenged Edge for the gold in the main event of WrestleMania 24. Edge seemed more than happy to win by any means, trying to get Undertaker counted-out on a few occasions. It was a different approach that nobody else had used against ‘Taker at WrestleMania. Edge thought he had the match won with a Spear, but got caught in the Hell’s Gate and gave up.
3 The Undertaker Vs. Triple H - Hell In A Cell Match (WrestleMania 28)
Overall Rating From TheSportster: 9.75/10
Storytelling | 2.5/2.5 |
|---|---|
Technical Ability | 2.25/2.5 |
Character Work/Psychology | 2.5/2.5 |
Crowd Reaction | 2.5/2.5 |
- Dave Meltzer's Rating: 4.75 Stars
- Cagematch.net Rating: 9.21
Triple H came back for more after the end of the WrestleMania 27 match. Feeling he had The Deadman’s number, Triple H challenged Undertaker to a Hell in a Cell Match at WrestleMania 28. Shawn Michaels was named special referee for this one, which meant he could still indirectly end the Streak after being retired by The Deadman.
10 Things WWE Fans Forget About The Build Up To WrestleMania 28
Everyone remembers The Rock vs. John Cena at WWE WrestleMania 28, but many fans forgot about some of the build up leading up to the big event.Many fans think this was the most dramatic match of the Streak, and that might very well be true. Triple H was close on many occasions yet again, especially when Michaels superkicked Undertaker right into The Game’s Pedigree. Somehow Undertaker kicked out and he found a way to win. The three legends embraced after the match in a truly unforgettable moment.
2 The Undertaker Vs. Shawn Michaels (WrestleMania 25)
Overall Rating From TheSportster: 9.75/10
Storytelling | 2.25/2.5 |
|---|---|
Technical Ability | 2.5/2.5 |
Character Work/Psychology | 2.5/2.5 |
Crowd Reaction | 2.5/2.5 |
- Dave Meltzer's Rating: 4.75 Stars
- Cagematch.net Rating: 9.61
This is a special match. Many people call it the greatest match in wrestling history, and for good reason. At WrestleMania 25, The Undertaker and Shawn Michaels put on a breathtaking performance that was simply unbelievable.
After Michaels kicked out of the Tombstone and Undertaker kicked out of Sweet Chin Music, it seemed nothing could take either man down. Eventually, Undertaker caught Michaels going for a moonsault and delivered a great Tombstone Piledriver to end this epic classic.
1 The Undertaker Vs. Shawn Michaels - Streak Vs. Career (WrestleMania 26)
Overall Rating From TheSportster: 10/10
Storytelling | 2.5/2.5 |
|---|---|
Technical Ability | 2.5/2.5 |
Character Work/Psychology | 2.5/2.5 |
Crowd Reaction | 2.5/2.5 |
- Dave Meltzer's Rating: 4.75 Stars
- Cagematch.net Rating: 9.51
The reason why we’re putting their second WrestleMania match ahead of the previous entry is because the storytelling was unquestionably better this time around. Shawn Michaels was desperate to end the Streak and put his own career on the line just to get a second chance.
Much like the year before, these two stole the show yet again by delivering a spectacular performance. Fans knew they’d witness history as either Michaels’ legendary career would end or the Streak would be over. In the end, Undertaker put The Heartbreak Kid’s career to bed after connecting with a thunderous jumping Tombstone.
