The Undertaker’s Streak became a key component of any WrestleMania match, with The Deadman winning 21 straight matches at the Showcase of the Immortals. But, which ones were his best? Here is every match from Undertaker’s Streak ranked from worst to best.
21. Vs Giant Gonzalez – WrestleMania IX
Giant Gonzalez was a 7-foot 7-inch monster, who towered over everyone he stepped in the ring with. The problem though, he had next to no wrestling ability, resulting in largely poor quality matches. The finish of the match saw Gonzalez defeat The Undertaker before the decision was reversed. Had WWE not booked the decision to be reversed, the worst WrestleMania match of The Undertaker’s career, and one of the worst of all time, could have ended The Streak before it ever really begun.
20. Vs King Kong Bundy – WrestleMania XI
By 1995, King Kong Bundy was well past his prime, but WWE brought him back and stuck him in a feud with The Undertaker which resulted in a really poor WrestleMania match. We’re so glad that WWE hired Mick Foley in 1996 and helped to break the pattern of Taker only working with big men.
19. Vs A-Train and Big Show (2-on-1 Handicap Match) – WrestleMania XIX
The match was originally scheduled to be A-Train and Big Show vs The Undertaker and Nathan Jones. Jones had been pitched as one of the next big WWE Superstars, but WWE seemed to lose faith in him. What made this even more strange was that Jones interfered in the match to help The Undertaker, so why not just put him in the match?
18. Vs Big Boss Man (Hell In A Cell) – WrestleMania XV
The Ministry and The Corporation were embroiled in a feud in the lead up to WrestleMania XV, with The Phenom taking on Big Boss Man at the Showcase of the Immortals inside Hell In A Cell. The match itself was fairly average, especially considering the quality of the Hell In A Cell matches we’d seen prior. After the match ended The Brood descended from the rafters and helped The Undertaker hang Boss Man by a noose from the top of Hell In A Cell.
17. Vs Diesel – WrestleMania XII
The Undertaker and big men never seem to pay off and that was the case again when he faced Diesel at WrestleMania XII. Both Superstars are capable of having a great match, but the chemistry just wasn’t there on this occasion.
16. Vs Kane – WrestleMania XX
The Undertaker vs Kane at WrestleMania 14 is one of the best matches of either men’s careers, their WrestleMania XX encounter…not so much. While it isn’t a bad match, both Superstars are much more capable than what we got at WrestleMania XX, it did mark the return of The Deadman persona though which is great.
15. Vs Jimmy Snuka – WrestleMania VII
The Undertaker’s first WrestleMania match was against Jimmy Snuka. Overall, the match was pretty good but Snuka was almost 50 at the time and in the twilight years of his career, it would have been great to see The Undertaker face Snuka in his prime, that would be a sight to see.
14. Vs Sycho Sid (WWF Championship) – WrestleMania 13
The Undertaker faced Sycho Sid in the main event of WrestleMania 13 for the WWF Championship, a match originally pencilled in to be Shawn Michaels vs Bret Hart. While not the match that was originally planned, it was still a pretty good match, but the show-stealer was without a doubt Austin vs Hart.
13. Vs Jake Roberts – WrestleMania VIII
Taker’s second WrestleMania match was against the legendary Jake “The Snake” Roberts at WrestleMania VIII. Despite a career plagued by drink and drug problems, when Roberts wanted to go he could go and this match proves that.
12. Vs Mark Henry (Casket Match) – WrestleMania 22
The World’s Strongest Man faced The Deadman in a Casket Match at WrestleMania 22, and as far as Casket Matches go it was really good. It would still be a few years before Mark Henry became a World Champion, but this match proved he could hang with the best.
11. Vs CM Punk – WrestleMania 29
The Undertaker faced CM Punk in Punk’s final WrestleMania match before he quit the company the following year. The story leading up to the match was fantastic too, with WWE using the recent passing of Paul Bearer to further Punk’s heel persona.
10. Vs Batista (World Heavyweight Championship) – WrestleMania 23
The Animal defended his World Heavyweight Championship against The Undertaker at WrestleMania 23 in one of the best matches of his career. Although Batista lost the match, it helped elevate him even further as a top star in the company.
9. Vs Randy Orton – WrestleMania 21
The Legend Killer looked to end The Streak in the first match where The Streak was referenced. Fun fact, The Undertaker wanted Randy Orton to win this match to help elevate him into a bigger star.
8. Vs Shawn Michaels (Career vs Streak) – WrestleMania 26
HBK’s career was on the line at WrestleMania 26, in a rematch from their WrestleMania 25 encounter. While not as good as their previous match, these two Superstars have unrivaled chemistry so this was another classic.
7. Vs Triple H (No Holds Barred) – WrestleMania 27
Following HBK’s retirement at WrestleMania 26, his former DX teammate wanted revenge against The Deadman. This no-holds-barred match was very hard-hitting, with some incredibly risky spots. Despite their age, they both proved that can still go when the bell rings.
6. Vs Edge (World Heavyweight Championship) – WrestleMania 24
If you’re billed to defend your World Championship against The Undertaker at WrestleMania, it is fair to assume that your title reign will be coming to an end very soon, and that was the case at WrestleMania 24 as The Deadman faced Edge. Both men will go down in history as two of the great Superstars of all time, so that says all you need to know about this match.
5. Vs Triple H – WrestleMania X-Seven
WrestleMania X-Seven featured one of the most stacked WrestleMania cards of all time, including TLC 2 and Steve Austin vs The Rock. For that reason, Triple H vs The Undertaker often gets overlooked, which is a travesty, this match is a classic.
4. Vs Ric Flair (No DQ) – WrestleMania X-8
Hearing the words Ric Flair and low self-esteem just sounds weird. How can the “limousine riding, jet flying, kiss-stealing, wheelin’ n’ dealin’ son of a gun” known as The Nature Boy be worried about whether he can wrestle? Unfortunately, that was the case when Flair made his way to WWE following the buyout of WCW in 2001. Worrying about his future as a competitor, Flair stepped into the ring at WrestleMania X-8 against The Undertaker, a program that Taker had personally requested, and the match proved that Naitch still had what it took to style and profile.
3. Vs Kane – WrestleMania 14
The Undertaker never had much luck when it came to working with big men, with most of the feuds falling flat. But, that all changed when his brother Kane made his debut of Badd Blood: In Your House to get revenge on The Undertaker, who left him to die in a fire as a child. The near year-long story that began in April 1997 finally came to a head as the two brothers stepped into the ring together as WrestleMania 14 in March 1998. The Undertaker and Glenn Jacobs (the man who portrays the Kane character) had previously met in Smokey Mountain Wrestling but had never worked together in WWE before their WrestleMania encounter, but the two had instant chemistry with each other and have both become synonymous with each other. This match is two Superstars in their prime and if you are a ‘Taker fan you need to watch this.
2. Vs Triple H (Hell In A Cell) – WrestleMania 28
The Hell In A Cell match at WrestleMania 28 was billed as “End of an Era”, as The Deadman stepped inside Satan’s Structure with The Game. This match is one of the most emotional matches we’ve seen in the WWE for quite some time and one that is definitely worth checking out on the WWE Network.
1. Vs Shawn Michaels – WrestleMania 25
At number 1 is The Undertaker vs Shawn Michaels at WrestleMania 25. Not only The Undertaker’s best WrestleMania matches, but it is often hailed as one of the best WrestleMania matches of all time, and one of the best wrestling matches of all time. The Undertaker and HBK have chemistry that is nearly unmatched in the wrestling industry and it was always magic every time these two Superstars stepped into the ring together.
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