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In the 27 WrestleMania matches The Undertaker has competed in, he has had his fair share of the best and worst matches in WrestleMania history. The Deadman's matches with the likes of Giant Gonzalez and King Kong Bundy are prime examples of The Undertaker's ability to make the best of a position where you can't make a match excellent.
However, on the other hand, The Phenom has worked some of the greatest matches in WrestleMania history with the likes of Ric Flair at WrestleMania X8, Randy Orton at WrestleMania 21, Batista at WrestleMania 23, Edge at WrestleMania XXIV, Shawn Michaels at WrestleMania XXV, Shawn Michaels at WrestleMania XXVI, Triple H at WrestleMania XXVII, Triple H at WrestleMania XXVIII, and CM Punk at WrestleMania 29. It seemed like as he got older, The Undertaker grew to have greater matches year-by-year.
From WrestleManias 23-29, The Undertaker had the best match of the night on each card, while extending the famous "Streak". Though The Lord of Darkness wasn't in the main event of many of those WrestleMania classics, he was always the focal point and the number one topic discussed, regardless of his placement on the card.
Throughout the years and decades that The Undertaker has been in WWE, he shockingly had a ton of dream matches left on the table, especially at WrestleMania.
Let's take a look at five more Undertaker matches that should have happened at WrestleMania!
#5 The Undertaker vs John Cena - WrestleMania XXX
Original match: The Undertaker vs Brock Lesnar
Other than Daniel Bryan's two great matches at WrestleMania XXX, the thirtieth anniversary of The Showcase of the Immortals fell flat in terms of starpower, match quality, and overall attraction.
At WrestleMania XXX, The Undertaker took on Brock Lesnar in a slow, plodding, and methodical match that resulted in one of the most questionable booking decisions in wrestling history, while John Cena took on Bray Wyatt in a match where the latter lost an abundance of momentum creatively.
By the time the year 2014 was on the horizon, The Leader of the Cenation and The Deadman rarely locked horns. In fact, both men only faced off once on pay-per-view, where the American Badass tamed the Doctor of Thuganomics at Vengeance 2003 prior to WrestleMania 34 in 2018.
In addition, the last singles match that took place between the two WWE legends was on an episode of Raw in 2006, where King Booker and Big Show interfered to attack both men.
If The Undertaker had interfered in the 2014 Royal Rumble match and tossed out John Cena, the clash would have been set.
#4 The Undertaker vs Sting - WrestleMania 31
Original match: The Undertaker vs Bray Wyatt
Ever since Sting morphed into The Crow during the glory days of WCW, fans and professional wrestling experts have fantasized a dream match between WCW's finest and WWE's finest; the two top antiheroes of their company. While Sting was slaying the NWO, The Undertaker was slaying his own brother.
When Vince McMahon purchased WCW on March 26th, 2001, there was immediate buzz surounding The Franchise of WCW and his intentions post WCW vs WWE. While many were hoping for Sting to sign with WWE from 2002 all the way to 2014, they still had hope for a WrestleMania match with The Undertaker.
Upon Sting's arrival at Survivor Series 2014, the WWE Universe was estatic to witness Sting's WWE debut, but they simultaniously felt underwhelmed that The Icon did not contront The Deadman.
Instead, if WWE had booked The Undertaker to return for the first time since WrestleMania XXX At Survivor Series to announce his intentions, Sting had debuted to interrupt WWE's cornerstone, where both men go face to face, there could have been a slow, but great build to a Sting-Undertaker match in WWE. This could have happened in the main event of WrestleMania 31.
#3 The Undertaker vs Brock Lesnar: WrestleMania 32 - Hell in a Cell Match
Original match: The Undertaker vs Shane McMahon: Hell in a Cell match
Instead of WrestleMania XXX, The Undertaker vs Brock Lesnar should have happened at WrestleMania 32. On a card that lacked a tremendous amount of starpower due to injuries, The Phenom taking on The Beast would have drawn in both the casual and hardcore viewers.
The story could have began with The Undertaker wanting redemption for The Beast beating him in his own game back at No Mercy 2002, where the rookie beat the American Badass to a bloody pulp in his very own match, Hell in a Cell. In this story, The Undertaker may not have forgetten that. However, this time, Brock Lesnar takes on The Deadman, not Big Evil.
Their Hell in a Cell classic at Hell in a Cell 2015 could have taken place at WrestleMania 32, except, The Undertaker hits a second Tombstone Piledriver to pick up the victory in his home state of Texas.
#2 The Undertaker vs "Demon" Finn Balor - WrestleMania 33
Original match: The Undertaker vs Roman Reigns: No Holds Barred match
Ever since the former Prince Devitt burst onto the scene as Finn Balor in late 2014 in WWE, many have compared the "Demon" persona to The Deadman himself. The Undertaker typically works better matches with smaller opponents, and it's highly likely that a match with Finn Balor would have worked well too.
It's no secret that The Phenom's hip was in horrible shape leading into WrestleMania 33, but he could still have pulled off an excellent match with the correct opponent. The likes of AJ Styles or Finn Balor would have been strong candidates to have given The Undertaker a great match at WrestleMania 33.
Placing the first ever Univeral Champion against the greatest performer in WrestleMania history would have elevated Balor in WWE. In many Undertaker matches, The Undertaker earns the victory, but his opponent becomes over just by being in the same ring as him, which could have happened with Finn Balor as well.
#1 The Undertaker vs Daniel Bryan - WrestleMania 34
Orginal match: The Undertaker vs John Cena
When it was announced on WWE.com that Daniel Bryan was cleared to make an in-ring return, the entire professional wrestling world erupted and began to speculate who the Leader of the Yes Movement would take on in his first match back. While his return match saw him team up with Shane McMahon to face Kevin Owens and Sami Zayn, many wanted to see the former WWE Champion be in a singles match upon his first match back in three years.
On the same night, The Undertaker returned and looked like he was in the best shape he had been in for years. Even The Deadman himself said he was planning on having a 25-30 minute match, but he ended up competing for just three minutes at WrestleMania 34 against John Cena.
Daniel Bryan could have been the man to face The Undertaker at WrestleMania 34, and he could have challenged a man he has never faced before in WWE - The Undertaker.
Following the WrestleMania clash, it could have served as a motivator for Daniel Bryan to turn heel and start his WWE Championship reign approximately five months earlier than originally slated.
