The WrestleMania streak of The Undertaker will always hold a special place in WWE history. Undertaker scoring 21 victories in a row before suffering his first defeat Mania was an amazing and unexpected phenomenon. WWE realized the streak was a big deal about a decade into it when starting to market it as such with elaborate opponents.
Even something as great as the streak would not go without hiccups along the way. There were quite a few flaws that lack logic or common sense looking back today. Undertaker made the entire body of work shine to become an all-time great draw for WWE. However, there were just some things from the icon’s undefeated WrestleMania streak that made no sense.
10 DQ Finish Vs Giant Gonzalez
The Undertaker had a tough task at WrestleMania IX, trying to lead the inexperienced Giant Gonzalez in a huge match. Gonzalez was Vince McMahon’s project of a new top monster heel in the early ‘90s when characters like that thrived.
Unfortunately, the in-ring skill and character work of Gonzalez led to him failing in the role. WWE did a terrible job booking a DQ finish for Undertaker’s win as the only indecisive victory of his undefeated streak.
9 Kane Losing To Him In Their First Match
WWE found huge success introducing Kane as The Undertaker’s brother in late 1997. Undertaker refused to fight Kane who continuously attacked him for months. The anger of Undertaker finally saw him having the big match at WrestleMania XIV.
Most stories with a new character having strong momentum like Kane would see him winning the first match. Undertaker winning worked out in the long run for obvious reasons, but the logic for the Kane loss was off at the time.
8 Removing Nathan Jones From Tag Match
Nathan Jones was someone WWE had strong hopes for when debuting him as the protégé of The Undertaker. WWE went as far as to book them in a tag match at WrestleMania XIX, knowing the streak was on the line.
The idea itself made little sense, but it was even worse when they removed Jones at the last minute to add confusion. Undertaker winning the handicap match was better for his streak, but it was confusing in 2003.
7 Big Boss Man Representing The Corporation Against Him
The Undertaker feuding with Vince McMahon led to a surprising match with Big Boss Man at WrestleMania 15. WWE booked one of the early Hell in a Cell matches since Undertaker was associated with the stipulation.
Big Boss Man was not treated like a main eventer at the time making it more confusing why he was picked. Vince could have picked Kane who was in The Corporation to start the night or elevate someone with more name value at the time like Ken Shamrock. Everyone knew Undertaker was easily winning this match heading into it.
6 King Kong Bundy Representing Million Dollar Corporation Against Him
Another instance of The Undertaker feuding with a faction featured Ted DiBiase’s Million Dollar Corporation attempting take him down. King Kong Bundy was the wrestler selected to face Undertaker at WrestleMania XI.
Many of the other members like Kama Mustafa or Tatanka had more value than Bundy in 1995. Bundy was older and struggled to move around the ring. WWE could have turned someone like Lex Luger heel for the match to improve the show.
5 Build For WM 13 Title Win
WWE was put in a tough position when Shawn Michaels chose to retire after the infamous speech of “losing his smile.” The planned main event of Michaels vs Bret Hart ended with WWE struggling to build a title match.
Sycho Sid won the WWE Championship and defended against Undertaker with everything rushed in the month before the show. Bret Hart vs Steve Austin had a stronger build and felt like the main event to take away from Undertaker’s big moment.
4 Match Vs Batista Not Main Eventing
Batista had one of the biggest moments of his career when booked strong as someone with a credible chance at ending The Undertaker’s streak. WrestleMania 23 featured the streak on the line against Batista’s World Heavyweight Championship in an outstanding match.
Both Batista and Undertaker were upset about getting snubbed from the main event spot. Shawn Michaels and John Cena had a great match to close the show, but the appeal of the streak and the feel-good moment of Undertaker winning the title deserved the main event.
3 Weak Build For Match Vs Brock
One of the main reasons fans had no idea Brock Lesnar could realistically end the streak at WrestleMania XXX was due to how weak the build was. WWE did little to make the match feel important compared to Undertaker’s past seven matches involving the world title or personal feuds.
A few segments of the two getting violent felt rudimentary heading into the match. An argument can be made that the poor-build helped add to the shock of Brock ending the streak, but the interest was nowhere near the Daniel Bryan story even though it had more historical importance.
2 Refusing To Give Shawn Michaels A Rematch
Shawn Michaels had the best match of The Undertaker’s undefeated streak at WrestleMania 25. Many regard this as the best overall outing in WWE history given the impact of the two legends involved in such a masterpiece.
The story for WrestleMania 26 featured Michaels desperate for a rematch and Undertaker refusing until pushed too far. This was done to introduce the retirement stipulation for Michaels but lacked logic for Undertaker’s character. The legend refusing to fight someone who pushed him to the edge was a strange concept.
1 Demanding Triple H Give Him A Rematch
The opposite scenario played out in the back-to-back matches for Triple H and The Undertaker. WrestleMania 27 featured Undertaker defeating Triple H in a great match to continue the streak. However, it was another odd story of getting to the rematch.
Undertaker was the one who begged for a rematch since Triple H brutally beat him the prior year before losing the match. Triple H finally agreed to provide an all-time great Hell in a Cell match, but it was still a confusing method of getting it booked.
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