10. WrestleMania X8 vs Ric Flair
This match subverted all the odds to become a WWE classic. Ric’s best days were certainly behind him, and ‘Taker certainly wasn’t producing the best fights of his career at the time. But the titanic clash between two of the sport’s biggest legends worked, sacrificing technique and detail for a more brutal approach.
9. WrestleMania X7 vs Triple H
This fight included some of WWE’s best moments, including the pair fighting in the crowd and the unbelievable chokeslam off the scaffolding. It signalled what was to come for the pair, long before they were putting on match of the year performances.
The fight surpassed all expectations and is considered by some to be one of the best WrestleMania fights between two legends.
8. WrestleMania 21 vs Randy Orton
This fight pitted a young Randy Orton against ‘Taker in 2005 and has become one of the most underrated fights of the legend’s career. It was the first time The Undertaker’s winning run had been labelled by WWE as ‘The Streak’, which helped to add fuel to the fire. The fight’s technical success saw it become the blueprint for many of his more recent WrestleMania performances.
7. WrestleMania XXIV vs Edge
The year-long rivalry between these two fighters will go down as one of the best in the sport. It was dramatized by their frequent injuries, which only helped to build the hype for when they finally met at WrestleMania. ‘Taker was ultimately successful, beating Edge and his team in stunning fashion to cement the bout as one of the most memorable.
6. WrestleMania 23 vs Batista
The in-ring chemistry in this bout caught a lot of fans off-guard, with the amazing physical storytelling making most fans worry that The Streak could be in jeopardy.
The Undertaker eventually went 15-0 while claiming the World Heavyweight Championship, but the 15-minute brutal bout will be remembered for far more than just this victory.
5. WrestleMania XXVII vs Triple H
The Undertaker fought old rival Triple H at WrestleMania XXVII in a bout which had some serious backstory and effective storytelling. Triple H was trying to avenge HBK’s retirement by defeating his rival, which made many fans believe that once again The Undertaker could be defeated. The stars went into all-out war, landing some huge blows constantly throughout the fight. ‘The Deadman’ eventually won with a well-timed Hell’s Gate, which helped set up the pair’s rematch the following year in stunning fashion.
4. WrestleMania 29 vs CM Punk
WrestleMania 29 paid tribute to Paul Bearer with a brilliant fight between ‘Taker and CM Punk. Punk tried to use the occasion to throw off his opponent, but this was unsuccessful as ‘The Deadman’ took the final victory of his streak.
Many fans praise Punk for seemingly carrying his opponent throughout the match, but this was a time in The Undertaker’s career where he was delivering all-time classics on a regular basis, this one included.
3. WrestleMania XXVIII vs Triple H
The duo managed to repeat their previous two fights in incredible style, helping to make their third fight one of the most memorable of them all. Billed as the End of an Era, the match was built on nostalgia of the sport’s glory years and certainly lived up to the hype.
The fight even managed to steal the show from The Rock and John Cena’s main event showdown, such was the admiration for the third fight between the pair.
2. WrestleMania XXVI vs Shawn Michaels
The Streak vs Career match pulled out all the stops, helping to make their rematch just as well respected as the first fight. Not only was Shawn Michaels’ career on the line, so was ‘Taker’s unbelievable streak of victories. This fight will go down in WWE history as an absolute classic from start to finish.
1. WrestleMania 25 vs Shawn Michaels
Michaels definitely knew how to bring about the best in The Undertaker, which is why their two fights come first and second on this list. Now in their mid-40s, the two veterans had to reignite some of their old techniques in order to truly pay homage to WrestleMania’s 25th anniversary event.
The pair went out there and put the rest of the fighters to shame with a show-stopping performance that had fans around the world stunned. The fighters actually didn’t need to turn the clock back, as they showed that they were at their very best during WrestleMania 25. That’s why this will go down as The Undertaker’s best appearance at WrestleMania.
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