10. The Undertaker vs. Ric Flair – WrestleMania X8
Ric Flair was dealing with self-confidence issues as he went into his match at WrestleMania X8. Having lost his mojo in the dying years of WCW, Flair felt he wasn’t fit to be in the ring with a top star like The Undertaker.
However, through Undertaker’s persistence, they got the match in the ring. It was really good as the two veterans worked a classic match. Arn Anderson got to have a WrestleMania moment when he hit his famous Spinebuster on Undertaker. After it all was said and done we received our first acknowledgment of the streak, as Undertaker held up all ten fingers to signify his tenth straight win.
9. The Undertaker vs. Randy Orton – WrestleMania 21
This was the first time that someone challenged the Undertaker to a match at WrestleMania with the intention of breaking his streak.
The young, cocky Randy Orton wanted to solidify his legacy as the Legend Killer at the demise of the legendary streak. The match was really good and featured an all-time great RKO as Orton countered a chokeslam into his signature move. While the match was good, it never reached the level of the matches that would steal the show at WrestleMania after WrestleMania just a few years later.
8. The Undertaker vs. Triple H – WrestleMania X-Seven
Yes, it is absurd that Mike Chiota was unconscious in this match for nearly the whole thing. With that out of the way, this was a good match that helped to make this the greatest WrestleMania of all time.
To set themselves apart from the other matches on the show, these men did a ton of crowd brawling during their match. They brawled their way over to a production rig where Undertaker promptly chokeslammed Triple H off of it. If you ignore the brightly colored crash-pad that Triple H landed on, this was a crazy stunt. After returning to the ring, the referee regained consciousness and counted the three as Taker hit the Last Ride.
7. The Undertaker vs. Batista – WrestleMania 23
This was the first match in a long line of matches that stole the show at WrestleMania. No one thought that Batista and The Undertaker would have as much chemistry as they ended up having, but they brought every bit of it to this match.
The two wrestled a great match that Batista thought should have been the main event of the show. You could make a very solid argument in favor of that statement, however, they were left to steal the show in the middle of the card. Their match brought the intensity of a big grudge match and the stakes of a World Championship match. Finally, Taker managed to hit the Tombstone and keep Batista down for the three. Taker won the World Heavyweight Championship for the first time and brought the streak to 15-0.
6. The Undertaker vs. CM Punk – WrestleMania 29
Just about the only notable thing to happen at WrestleMania 29 was this match. CM Punk was upset that he was not in the main event of the show after spending 434 days as WWE Champion.
Punk took that anger and tried to have the best match possible with The Undertaker. He succeeded and had by far the best match on the show. While there was no moment in the match that fans believed that Punk was actually going to break the streak, there was great drama throughout. Punk and Paul Heyman had taken control of the urn following the death of Paul Bearer. They used the urn to get a nearfall on ‘The Deadman’ but in the end, it was The Undertaker who got the upper hand. He hit a Tombstone and the pin.
Little did we know that this would be the final time the streak would be successfully defended.
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