The Undertaker’s WrestleMania performances helped create an amazing legacy. Fans would wait in anticipation each year to find out which wrestler was going to get a chance to end Undertaker’s undefeated WrestleMania streak. Incredible matches against top names like Batista, Edge, Shawn Michaels, and CM Punk helped make the undefeated streak one of the most beloved ideas in wrestling history. WWE didn’t plan the undefeated streak from day one, but the organic movement helped create something special.
Brock Lesnar was the first man to defeat The Undertaker at WrestleMania XXX, which launched the beast's era of dominance. Undertaker’s WrestleMania match is still an important deal years after the undefeated streak ended. Fans want to see what magic can come from Undertaker’s match on the biggest stage. We will look at five of the top wrestlers Undertaker should have faced at WrestleMania along with five of his pointless opponents.
10 Should have wrestled: Mick Foley
The Undertaker’s feud with Mick Foley created great matches and moments in WWE history. Foley was introduced as the Mankind character which served as the perfect opponent for Undertaker. Paul Bearer even turned on Undertaker to unite with Mankind in a memorable Boiler Room Brawl.
These two could have had a classic match at WrestleMania in the late '90s when they were in their prime. It would have benefited both wrestlers since they had a few disappointing opponents in that time frame. Undertaker’s rivalry with Foley was one of the best of his career and deserved a WM match.
9 Pointless opponent: Roman Reigns
WWE placed Roman Reigns against The Undertaker at WrestleMania 33 in an attraction match. The finish would see Undertaker lose his second WrestleMania match ever, with Reigns winning the main event. WWE’s presentation implied that Undertaker was retiring after leaving his gear in the ring.
The match was an embarrassing one for Undertaker as he noticeably botched a few stunts. Reigns did not get much from the win as Undertaker returned to the ring making the implied retirement feel less important.
8 Should have wrestled: The Rock
The Attitude Era featured both The Undertaker and The Rock as two of the most beloved top stars of the time. Undertaker and Rock faced off on a couple of occasions and even teamed together, but they never had a singles match on the biggest stage of them all.
Rock had three WrestleMania matches against Steve Austin which all delivered, but one against The Undertaker could have been a fun change of pace. This could have been a valid WrestleMania main event to get fans excited about the two icons facing off.
7 Pointless opponent: Big Show & A-Train
WrestleMania XIX stands out as one of the worst ideas WWE had for Undertaker at WrestleMania. This was around the time the undefeated streak started to become a major part of his WrestleMania matches and storylines.
WWE booked Undertaker in a tag match teaming with new star Nathan Jones against Big Show and A-Train. The idea was somewhat scrapped with Jones being written out and Undertaker ultimately winning the handicap match. It was a huge waste, especially as the roster was loaded in 2003.
6 Should have wrestled: Sting
One of the biggest dream matches in wrestling history was to see icons Sting and The Undertaker face off at some point. Their '90s runs would see them serve as locker room leaders in opposing companies as Sting was WCW’s icon and Undertaker was a top name for WWE.
Sting would not join WWE until the end of his career in 2014. WWE opted to pass on the dream match fans wanted by booking Sting against Triple H and Undertaker against Bray Wyatt. Both matches were nothing special and Sting retired before we could get the match we truly wanted.
5 Pointless opponent: Giant Gonzalez
During the early '90s, WWE produced many regretful ideas, including Giant Gonzalez. WWE put the over 7-foot-tall man in a weird bodysuit that made him come off as a joke rather than the monster heel the company wanted from this gimmick.
Undertaker faced off with Gonzalez at WrestleMania IX in arguably his worst WM match. WWE did not value the streak yet as Undertaker won the match by disqualification. Their feud was a huge disappointment and WWE released Gonzalez shortly after the match.
4 Should have wrestled: Steve Austin
Steve Austin and The Undertaker had a few great storylines and PPV matches in the late 90s. Their biggest match came in the main event of Summerslam 1998 at Madison Square Garden in and it felt like the most anticipated match of the year for WWE.
Unfortunately, we never got to see the two legends square off on the biggest stage. Austin and Undertaker would have had a classic on WrestleMania. Many fans hoped to see it at WrestleMania X8 instead of Austin’s bad match with Scott Hall and Undertaker’s forgettable match with Ric Flair.
3 Pointless opponent: Big Boss Man
The start of Undertaker’s new heel character leading the Ministry of Darkness saw him adding more terrifying elements to his act. Big Boss Man felt the wrath of Undertaker in a Hell in a Cell match at WrestleMania XV that ended with Undertaker hanging Boss Man by a noose as the cell raised.
WWE wanted to have this powerful imagery leave a memorable impact on the viewer. It instead just turned out to be a disappointing match before the moment. Big Boss Man was a Hall of Famer, but he was nowhere near the level of Undertaker in 1999, who should have had a far better opponent.
2 Should have wrestled: Kurt Angle
One of the most bittersweet matches in WWE history came at No Way Out 2006 when Kurt Angle and The Undertaker had a classic match for the World Championship. Angle retained in what is still considered one of the best matches of Undertaker’s entire career.
While a great match, it could have easily been saved for one month later at WrestleMania 22. Angle was at his peak in WWE and Undertaker was starting to deliver his best in-ring work as well. This match would be remembered more fondly if these two faced off on the bigger stage.
1 Pointless opponent: Mark Henry
Fans wanted to see The Undertaker face Kurt Angle for the World Championship at WrestleMania 22, but he instead worked against Mark Henry. Despite the use of Henry improving compared to prior years, he was not viewed as nearly as big of a star as Undertaker,
Bruce Prichard claimed on his podcast that the idea was pitched for Henry to end the undefeated streak before everyone took a step back to realize that would have been a mistake. The match itself should have been scrapped as no one believed Henry had a chance. Undertaker’s WrestleMania 22 was wasted in the lackluster Casket Match against Henry that fans barely remember today.