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5 Undertaker matches that should have happened at WrestleMania 

The Undertaker following his World Heavyweight Championship victory at WrestleMania 23 against Batista
The Undertaker following his World Heavyweight Championship victory at WrestleMania 23 against Batista

For three decades, The Undertaker has haunted WWE and competed against many of the top performers at the main event level.

On the other hand, The Phenom has not faced nearly every top name at WrestleMania, even though he has competed at 27 out of 36 WrestleManias.

Instead of facing new opponents every year, The Undertaker spent three WrestleManias competing in a trilogy with Triple H, while having the two greatest matches in WrestleMania history against Shawn Michaels, which adds up to five matches with two of the same opponents.

In addition, The Undertaker spent many WrestleManias carrying other opponents to superstardom such as Giant Gonzales, King Kong Bundy, Sycho Sid, Big Bossman, Big Show, A-Train, Mark Henry, Bray Wyatt, and Roman Reigns, just to name a few. What other names could have replaced these opponents? Could we have finally seen the dream match we all wanted for the better part of two decades? Could we have finally seen The Undertaker and Sting one-on-one at the biggest show of the year? It was a big possibility at one time.

Though, there are many other Superstars The Undertaker could have faced at WrestleMania with main event magnitude

Though the days of The Deadman being a full-time performer were numbered nearly a decade ago, WrestleMania was always the constant during the year for The Undertaker, even if it was his only match that specific year.

Whether it was the New Generation, Attitude Era, Ruthless Aggression Era, or PG Era, there have been many WrestleMania showdowns that we've missed out on from The Undertaker, whether he was injured, or WWE had other plans.

Let's take a look at five performers that The Undertaker should have had one-on-one matches with at The Showcase of the Immortals!


#5 The Undertaker vs Bret Hart: WrestleMania IX & WrestleMania XI

Bret Hart
Bret Hart

Original match: The Undertaker vs Giant Gonzalez.

In many of The Undertaker's early WrestleMania matches, he ran into an abundance of bad luck, by being placed with either in-ring veterans past their prime, or gigantic big men who were tremendously limited at that specific time.

In relation, Bret Hart was in the same situation as The Deadman for WrestleMania's IX, X, and XI. "The Excellence of Execution" faced the over five-hundred pound Yokozuna in consecutive WrestleMania main events at WrestleMania IX and X, while facing the aging Bob Backlund in an "I Quit" match at WrestleMania XI. Additionally, Hart even went on record to say that his clash with Backlund was the worst singles match he's ever had.

As for The Undertaker, he attempted to bring best out of the near eight-footer, but the match ultimately fell flat, and is notorious for being one of the worst matches in WrestleMania history. Then, two years later at WrestleMania XI, The Undertaker was a victim of circumstance again as he faced King Kong Bundy in a six-minute affair.

Both The Hitman and The Phenom had the ability to carry opponents at a high level, and placing them against each other at the Grandest Stage of Them All would have been the first great WrestleMania series at the main event level. The Undertaker vs Bret Hart for the WWE Championship at WrestleManias IX and XI respectively would have been two matches fans would've remembered forever as WrestleMania classics; look at their SummerSlam 1997 main event as an example.

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