Undertaker’s return last Monday at the 1,000th episode of Raw got me thinking — there is no doubt that in all the annals of professional wrestling the Undertaker’s WrestleMania winning streak of 20-0 is one of the most impressive. Yet, looking at the opponents over the years it does raise some questions about why it doesn’t include more of the top WWE main event stars. That’s a shame.

During the first five years of his winning streak, the Undertaker faced Jimmy Snuka, Jake Roberts, Gonzalez, King Kong Bundy, and Diesel. It is understandable that for WrestleMania VII, the Undertaker didn’t have a match with top talent such as Randy Savage, Ultimate Warrior, Sgt Slaughter and Hulk Hogan due to the fact that he was a relative newcomer to the company. However, after WrestleMania VII he won his first WWE championship against Hulk Hogan at the 1991 Survivor Series. A win over Hulk Hogan during that era was very rare and a clear indication that the Undertaker was now being thought as a main event star. So after the 1991 Survivor Series there was a logical expectation amongst many that the Undertaker would face, Hulk Hogan, Randy Savage, Ric Flair (who won the WWE championship at the 1992 Royal Rumble) or even Sid Justice at WrestleMania VIII. Instead, the Undertaker went on to face Jake Roberts, which while one of the best matches on the card, seemed a step down from facing one the aforementioned WWE superstars.

Shawn Michaels and The Undertaker help Triple H out of the ring after ‘Taker beat him at WrestleMania 28. Photo by Mike Mastrandrea

During the period from WrestleMania IX to WrestleMania XI, the top stars in the WWE were Bret Hart, Shawn Michaels, Yokozuna, Lex Luger, and Diesel, none of whom the Undertaker faced at WrestleMania until WrestleMania XII. At WrestleMania XII, the Undertaker arguably faced his first main event star in the prime of his career, Diesel. For the next two years at Wrestlemania, the Undertaker went on to face Sycho Sid (formally Sid Justice) and Kane, both of whom at that point in time were two main event stars. However, at WrestleMania XV, the Undertaker was placed in a match against the Big Boss Man, who was well past the prime of his career and a long way away from facing either Steve Austin or The Rock. In fact, during the WWE Attitude Era, the Undertaker would never have a match with either one at Wrestlemania. The only other main event star that the Undertaker would face at a WrestleMania during the Attitude Era would be Triple H at WrestleMania 17.

From WrestleMania 18 to WrestleMania XX, the Undertaker faced Ric Flair, Big Show and A-Train in a handicap match, and Kane for a second time. The top main event stars at these Wrestlemanias were The Rock, Hulk Hogan, Steve Austin, Chris Jericho, Kurt Angle, Brock Lesner, Bill Goldberg, Triple H, Shawn Michaels, Chris Benoit, and Eddie Guerrero.

It would not be until WrestleMania 21 when the Undertaker started to face a main event star as his opponent each year. Randy Orton and Mark Henry were considered very close to main event status.By WrestleMania 23, there was no doubt that a different decision was being made with respect to the Undertaker’s WrestleMania opponents. The Undertaker would go on to face Batista, and then Edge the following year at WrestleMania 24.

However, in the eyes of many it is the matches the Undertaker has had against Shawn Michaels at WrestleMania 25 and 26, and against Triple H at WrestleMania 27 and 28, which elevated the winning streak to the current legendary status it resides at.

Is the Undertaker’s WrestleMania winning streak less impressive by the fact that it doesn’t include any matches against Hulk Hogan, Randy Savage, Bret Hart, The Rock, Steve Austin, Mankind, Chris Jericho, Brock Lesner, Bill Goldberg, Eddie Guerrero, Chris Benoit, and Kurt Angle? Yes. Out of that list Hulk Hogan, Bret Hart, The Rock, and Steve Austin, defined the eras they wrestled in. The fact the Undertaker never wrestled any of those four top stars at WrestleMania is strange and leads to a great deal of speculation as to why it never happened.

There is also one major WWE main event star whom hasn’t been mentioned yet, which is John Cena. During the years of Cena’s ascendancy in the WWE, the Undertaker faced several other top stars, so for that period of his career, one can’t really say the winning streak suffered. Yet, John Cena is the wrestler who has clearly defined this post Attitude Era more than any other, and if the Undertaker doesn’t have a match with him at WrestleMania it would further lessen the greatness of the winning streak. A match between the Undertaker and John Cena would come with a lot of intrigue due to the fact that many fans feel John Cena has been aggressively pushed to the top of the card. There would be a general belief that WWE management would do the unthinkable and have Cena be the one to end the WrestleMania winning streak.

There have been many rumours that Brock Lesner’s return to the WWE is primarily for a match against the Undertaker at WrestleMania 29. However, due to Cena’s recent victory over Lesner on PPV, it doesn’t seem likely that wrestling fans will be able to suspend their belief that Lesner has a credible chance to beat the Undertaker at WrestleMania 29. Therefore the logical opponent for the Undertaker at WrestleMania 29 is John Cena and if the WWE doesn’t choose to setup that match they will be doing an enormous disservice to the fans and the legacy of the Undertaker’s WrestleMania winning streak.