Wrestlemania XV – vs. The Big Boss Man (Hell in a Cell match) (1999) – 8-0
The Big Boss Man enjoyed a highly successful first run with the WWF in the late 80s & early 90s, including feuds with Hulk Hogan and a tag team run with Akeem as The Twin Towers. He headed to WCW for about five years and then made his way back to the WWF in the fall of 1998. He became the head of security for Vince McMahon’s Corporation. While most fans fondly remembered Boss Man, he never achieved the glory of his prior stint and was looked upon as a true longshot to defeat The Undertaker in any match, not to mention a Hell in a Cell match, especially at Wrestlemania. What may have been the most impactful reason was the recent revamping of The Undertaker’s character into the head of The Ministry. It’s highly unlikely the creative team of the WWF would invest the time and effort to retool a major talent’s character and direction only to have him lose in a specialty match custom suited for him against a performer who is several years removed from his best run in any wrestling promotion. And they didn’t.
Wrestlemania X-Seven – vs. HHH (2001) – 9-0
Hunter Hearst Helmsley had become one of the top draws in the WWF. He had shed the Connecticut blueblood aspect of his gimmick entirely and was now, and forevermore, The Game. The Undertaker had shed his Dead Man persona and re-emerged with a new biker/tough guy image and became known as The American Badass. The conflict between these two boiled down to bragging rights. HHH demanded to be a part of the ‘Mania title match since he had defeated everyone in the WWF, including main event participants The Rock and Stone Cold Steve Austin. The Undertaker took objection to this remark, as HHH had never defeated him. In what would become an instant classic, The Cerebral Assassin and Big Evil faced off to see which dog would rule the yard (WWF). Of all the match-ups to this point, this is the first I believe Undertaker may have been in danger of losing. It’s also about the same time when announcers and fans started acknowledging “The Streak.” Personally, I think HHH saw this match as a rite of passage for his character and a showing of respect to The Undertaker. It certainly didn’t harm his standing in the company (of course, marrying a McMahon surely didn’t hurt either) to become a victim to the dark side.
Wrestlemania X8 – vs. Ric Flair (No DQ) (2002) – 10-0
After Flair, as co-owner of the WWF, condemned The Undertaker’s actions and interfered in his match against the Rock, ‘Taker challenged The Nature Boy to a Wrestlemania confrontation. Ric refused initially, but after The American Badass targeted his friends and family members in the following weeks, Flair acquiesced.
In a brutal and bloody brawl, Flair enlisted the aide of long-time friend and former Horseman Arn Anderson to try and defeat The Phenom. Despite a No DQ stipulation and several chairshots, Flair failed to disrupt the pin after a Tombstone piledriver. While the dirtiest player in the game might have been expected to garner the win in a prior decade, his primarily non-wrestling role left him ripe for defeat at the hands of the now 10 and 0 Undertaker and The Streak truly came to the forefront in ‘Taker’s career.
Wrestlemania XIX – vs. A-Train & The Big Show (Handicap Match) (2003) – 11-0
The Undertaker truly had the deck stacked against him at Wrestlemania XIX. He was scheduled to face A-Train & The Big Show in tag team action with his protégé, Nathan Jones. After Jones was attacked backstage and deemed unable to compete (rumor has it WWE officials decided at the eleventh hour to pull Jones from the match due to his lack of experience and recklessness in the ring), The Undertaker proceeded to the match to take on both men. Despite being at a disadvantage, The Phenom fought valiantly, and thanks to a distraction by an “injured” Jones, was eventually able to pin A-Train (definitely the lesser of the two opponents, though arguably neither were the caliber of opponent now necessary to have a chance at Wrestlemania against The Undertaker) via a Tombstone piledriver. It would be interesting to know if the creative team had intended for ‘Taker/Jones to win the match initially, and if they had lost, how that would or would not have affected the solo streak, but by overcoming the odds, the legacy of The Undertaker continued to grow.
Wrestlemania XX – vs. Kane (2004) – 12-0
The first Wrestlemania rematch for The Undertaker would come in a challenge from his brother, Kane. Five years removed from their initial match, Kane had proved himself to be a dominant force in WWE and now had to be looked upon as the odds-on favorite to break The Streak. He had defeated The Undertaker in other matches at other events, so why should WM XX be any different? Not so fast … Undertaker had not been seen since losing a Buried Alive match against Mr. McMahon at the previous year’s Survivor Series. McMahon, with the help of Kane, had been able to defeat The American Badass persona of The Undertaker. Making his return to as The Dead Man in classic ‘Taker garb, and even enlisting the aid of Paul Bearer, The Undertaker refused to bow to defeat as the Creatures of the Night cheered him on to yet another Wrestlemania victory.
Wrestlemania 21 – vs. Randy Orton (2005) – 13-0
Randy Orton was a fresh, young Superstar fresh off his first major title victory the year before as a part of Evolution and now coming into his own with his “Legend Killer” angle. He was also the first opponent to summarily focus his intention on ending the Wrestlemania streak of The Undertaker. Many fans believed Orton would win to elevate himself and his career and further establish his “Legend Killer” status. Orton’s confidence seemed to increase as the match got closer, but despite the interference of his father, “Cowboy” Bob Orton, he would succumb to The Dead Man. After arrogantly attempting to win the match by executing a Tombstone piledriver on ‘Taker, Orton’s attempt was reversed instead and led to another victory for The Phenom, and, as with HHH before, seemed to become a rite of passage for WWE Superstars.
Wrestlemania 22 – vs. Mark Henry (Casket Match) (2006) – 14-0
Mark Henry had no shot here. Even on his best day, Henry’s best chance at beating The Undertaker at Wrestlemania would be minuscule. After costing ‘Taker a chance at winning Kurt Angle’s World Heavyweight Championship, UT laid down the challenge and made quick work of The World’s Strongest Man, closing the casket just under the 10 minute mark.
Continued on page three …
