5 Undertaker matches that should have happened at WrestleMania

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

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.

#4 The Undertaker vs Mankind: WrestleMania 13 - No Holds Barred Match for the WWE Championship

Original match: The Undertaker vs Sycho Sid (C) - WWE Championship.

Upon Mankind's arrival to WWE the night after WrestleMania XII in April of 1996, it seemed like Vince McMahon and WWE had just found The Undertaker's next top rival. It turns out, "Mrs. Foley's baby boy" had fully ditched Cactus Jack and morphed into Mankind to take on WWE's own Grim Reaper.

Mankind and The Undertaker competed in a match at King of the Ring 1996, a Boiler Room Brawl at SummerSlam 1996, a Buried Alive match at In Your House 11: Buried Alive, a match at Survivor Series 1996, a match at In Your House 14: Revenge of the 'Taker, and a Hell in a Cell match at King of the Ring 1998, where Mankind was famously thrown off the roof of the structure.

To the casual and hardcore fan, it seems ludicrous that The Undertaker and Mankind have collided everywhere except WrestleMania, just based on their legendary Attitude Era rivalry alone.

At WrestleMania 13, Mankind teamed up with Vader to take on Owen Hart and the British Bullin a NO DQ tag team match for the titles, while The Undertaker faced Sycho Sid in a forgettable WrestleMania main event that was overshadowed by the legendary Bret Hart vs Stone Cold Steve Austin classic.

With the chemistry the WWE Hall of Famer and The Phenom had, a match between them in the WrestleMania 13 main event would have still been discussed to this day.

#3 The Undertaker vs Terry Funk: WrestleMania XV - Hell in a Cell Match

Terry Funk wrestling at an ECW event in the mid-1990s

Original match: The Undertaker vs Big Boss Man - Hell in a Cell Match

The Undertaker vs Terry Funk always semmed like a match that should have happened multiple times. However, The Funker and The Deadman never engaged in a singles match with one another.

Legendary manager and booker, Jim Cornette, claims that he would have booked The Undertaker to take on Terry Funk at WrestleMania X8 if he was booking the infamous Invasion storyline; many fans would not have disagreed with the former Smoky Mountain Wrestling owner.

The seeds were planted for a Funk and Undertaker showwdown during the famous Hell in a Cell match at King of the Ring 1998, where The Undertaker literally chokeslammed the territorial legend's shoes off his feet. From there, it seemed like the two were destined for battle.

With a prolonged story from July 1998 to March of 1999, The Lord of Darkness and the aging brawler could have told a slow story of the gunfighter coming back for one last fight against the new sheriff in town.

A main event feud with WWE's top star could have been a perfect way for Terry Funk to go out, along with giving the audience a classic story for them to remember for ages.

#2 The Undertaker vs Chris Benoit: WrestleMania XIX

Original match: The Undertaker vs Big Show and A-Train - 2-on-1 Handicap Match

For five years, The Undertaker and Chris Benoit were Smackdown's most reliable and consistent Superstars. However, it is mind-boggling that the two Smackdown originals only crossed paths in one pay-per-view singles match, at Rebellion 2000, where The American Badass was victorious.

Though both men rarely encountered each other, fans in the Ruthless Aggression Era salivated over a feud between The Undertaker and Chris Benoit. Unforunately, WWE never booked the feud, even though there was a five-year window to do so.

Furthermore, prior to WrestleMania 23, the former World Heavyweight Champion claimed in an overseas interview that there was one big singles program left for him to do, and that was a showdown with The Phenom.

As for Benoit's technical ability, his style would have meshed perfectly with The Undertaker's ability to adapt to any wrestling style his opponent possesses, which was seen in his unique chemistry with the likes of Bret Hart and Kurt Angle, who wrestled in a similar manner to Benoit.

When WrestleMania XIX rolled around in 2003, Big Evil was placed in a throwaway handicap match with Big Show and A-Train while The Canadian Crippler was tossed in a triple-threat tag team match with Los Guerreros, The World's Greatest Tag team, and Rhyno. As great as WrestleMania XIX was, a guaranteed wreslting clinic between two of Smackdown's finest could have placed it up there with the revered WrestleMania X-Seven.

#1 The Undertaker vs Kurt Angle: WrestleMania 22 - World Heavyweight Championship

When Kurt Angle defected from Raw to Smackdown in Janaury of 2006 to win the World Heavyweight Championship in a Battle Royal, it seemed like there was only a limited number of challengers for "The Olympic Gold Medalist" to defend his newly won title against, and The Undertaker was at the top of that short list.

Prior to 2006, The Undertaker had not participated in what many call a "WrestleMania classic", even though he had a great match with Triple H at WrestleMania X-Seven and another great match with Ric Flair the following year at WrestleMania X8. However, a showdown with The Olympic Hero would have removed all doubt whether of not The Undertaker had a classic at The Showcase of the Immortals or not.

For instance, the chesmistry Angle and The Deadman had is undeniable. Both men had two matches rated 4.5 stars just on Smackdown (September 4th, 2003 and March 3rd, 2006 respectively). In addition, their No Way Out 2006 classic is regarded by many as the greatest wrestling match of 2006.

If you placed the exact match from No Way Out 2006 into the main event of WrestleMania 22 with anouter ten minutes added, there would be two different scenes:

Scene 1: The Undertaker and Kurt Angle have a five-star WrestleMania main event.

Scene Two: The Undertaker adds Kurt Angle as victim number fourteen on The Streak.

Edited by Nishant Jayaram