To celebrate the Undertaker’s illustrious career, I’m looking back at his WrestleMania matches against “The Heartbreak Kid” Shawn Michaels and Triple H.
The Date: 5 April 2009
The Venue: Reliant Stadium; Houston, Texas
The Commentary: Michael Cole, Jerry “The King” Lawler, and Jim “J.R.” Ross
The Referee: Marty Elias
The Stakes: Singles match with the Undertaker’s WrestleMania winning streak on the line
The Build-Up:
Over his decorated career in World Wrestling Entertainment (WWE), the Undertaker amassed the greatest winning streak in wrestling history – 21 WrestleMania wins between 1991 and 2013 – and battled a who’s-who of the biggest names in wrestling. One of his most notable adversaries was “The Heartbreak Kid” Shawn Michaels, once one of the biggest prima donnas in the industry who (alongside his “Kliq” buddies) held a great deal of sway over WWE Chairman Vince McMahon. The Undertaker and HBK battled on and off throughout the 1990s, making history in the first-ever Hell in a Cell match. Some time after his dramatic comeback and notable character change, HBK was embroiled in a bizarre feud with John “Bradshaw” Layfield/JBL after finding himself low on cash, which was the background to Shawn challenging the Undertaker’s WrestleMania winning streak. After defeating both JBL and Vladimir Kozlov, Shawn earned the right to battle the Undertaker at what was billed as WrestleMania’s 25th anniversary, with HBK attacking the Deadman after they teamed up on Raw. The two engaged in a war of words, with HBK expressing his respect but lack of fear towards the Undertaker and backing this up by never flinching when the Undertaker employed his signature spooky gimmicks. HBK even donned white attire that mirrored the Undertaker’s and cast himself, as a born again Christian, as the natural contrast to the Phenom’s darkness, establishing both men as uncompromising forces of nature heading into the match.
The Match:
This contrast of light and dark continued at WrestleMania 25, with Shawn Michaels descending from the heavens in his white attire while the Undertaker ascended from the stage, surrounded by lightning and flames. The visual of the two legends in the ring was enough to elicit a near-deafening buzz from the crowd, who watched with anticipation as the two danced around each other and exchanged strikes in the early going, with HBK using his speed to dodge the Undertaker’s reach and landing chops and forearm shots. The Undertaker quickly asserted himself, catching HBK’s fist and launching him into (and over) the corner, only for Shawn to pounce upon the Deadman after feigning a knee injury. Annoyed, the Undertaker overpowered Shawn and unleashed a flurry in the corner, finally dropping HBK and taking control of the match. Shawn weathered the assault and continued to fire back with knife-edge chops, only to be turned upside down off an Irish whip into the far corner and a back body drop. The Undertaker showcased his incredible strength with a military press slam and scored a one count off a running elbow before focusing on Shawn’s left arm, wearing him down for his signature rope walk. Wily as ever, HBK dodged at the last second when the Undertaker went for a running big boot, leaving the Deadman hung up in the corner, then targeted the Phenom’s left knee to chop the big man down. The crowd erupted as HBK applied the Figure Four Leglock to further punish the Undertaker’s leg, scoring a quick one count but eventually releasing the hold when the Undertaker punched him in the face.
While HBK continued to target the knee, the Undertaker fell back on pure power, muscling Shawn into the corner for another beat down but noticeably hobbling as he landed a couple of body splashes and his signature Snake Eyes/Big Boot combination. The follow-up leg drop scored the first two count of the match and, frustrated, the Deadman called for a Chokeslam. Shawn surprisingly countered with a Crippler Crossface, maintaining the hold even as the Undertaker desperately rolled into a pinning predicament and powered up. The Deadman bought a reprieve and earned a near fall off a side slam and the two went back to exchanging blows, with the Undertaker getting madder with each strike. HBK exploded off the ring ropes for his trademark forearm shot and leapt to his feet, landing two inverted atomic drops and dropping the Phenom with a running clothesline. Even when the Undertaker snatched him out of mid-air as he went for his patented top rope elbow drop, HBK countered with a low kick and tried for the Figure Four again, only to end up the Undertaker’s “Hell’s Gate” hold! After HBK scrambled to the ropes to break the hold, the competitors tumbled outside, where the Undertaker bashed HBK’s face off the ring steps, only to miss his apron leg drop, further damaging his leg. Shawn followed up with a baseball slide but crashed and burned off a moonsault to the outside, giving the Undertaker time to catch his breath. As Shawn struggled to his feet and refused to quit, the Undertaker flew over the ropes with a suicide dive and damn-near killed himself when the “cameraman” failed to catch him! Desperate to buy the Undertaker time to recover and win by any means necessary, HBK dragged the referee into the ring to begin a ten count, only for the Deadman to (eventually) roll back into the ring, much to Shawn’s utter dismay.
Enraged, HBK tried for Sweet Chin Music, only to get hit with a Chokeslam and barely kick out at two! However, after slipping out of a Tombstone Piledriver and shrugging off another Chokeslam attempt, Shawn finally hit his signature super kick, only to take too long making the cover and for the Undertaker to kick out. After a defiant kip up, Shawn almost got nailed with the Last Ride, only to squirm out of it and attempt a cover, which the Undertaker reversed to finally drill HBK with his massive powerbomb…for a two count! Incensed and amazed, the noticeably groggy Undertaker uncharacteristically climbed the top rope, only to eat the canvas when HBK dodged his diving elbow drop. After both struggled up, Shawn got dropped with a Tombstone Piledriver after attempting a headscissor from the ring ropes. Unbelievably, HBK kicked out just before three, much to the distraught Deadman’s chagrin. The Undertaker dropped the straps and did his signature throat cut taunt to signal a second Tombstone Piledriver, only for HBK to desperately counter with a DDT. Shawn followed up with his diving elbow drop and summoned all his strength for another Sweet Chin Music…and another heart-stopping two count! Both men clutched at each other and returned to throwing strikes, barely able to stand and being equally matched and stubborn. Though HBK fought out of another Tombstone attempt and countered a running corner splash, his luck ran out when he went for a Moonsault and got caught in mid-air and drilled with a Tombstone Piledriver, giving the Undertaker his seventeenth WrestleMania win. I really enjoyed the story being told here of the tenacity and pig-headedness of both men, who refused to quit or stay down and kept finding the will to continue. I also liked that it wasn’t just a finisher- or spot-fest and that they sold their biggest shots as potential match enders and grew increasingly frustrated and desperate when their opponent somehow kicked out. However, it’s a shame all that focus on wearing down the arm and leg didn’t factor into the end that much.
The Aftermath:
Widely regarded by many, including the Undertaker, as one of the best matches of either man, this bout was listed as WWE’s greatest WrestleMania match of all time, and it’s easy to see why (even with that botched dive). Following their gruelling contest, both men took four months off to recuperate. When Shawn Michaels returned later that year, he re-formed D-Generation X with his long-time friend Triple H and got into it with the upstart Legacy faction while the Undertaker distracted himself capturing CM Punk’s World Heavyweight Championship in a Hell in a Cell match. At the 2009 Slammy Awards, the WrestleMania 25 match won “Best Match of the Year”, prompting HBK to challenge the Undertaker to a rematch. When the Deadman turned down the challenge, believing he had proved himself the superior, HBK became obsessed with getting another shot at the Streak. After he failed to win the 2010 Royal Rumble match and legitimately earn a shot at the Undertaker’s championship, HBK cost the Deadman the World title at Elimination Chamber, finally goading the Undertaker into a rematch but with one caveat: HBK’s star-studded career would also be on the line!
My Rating:
Fantastic
Did you enjoy the Undertaker’s captivating match with Shawn Michaels from WrestleMania 25? How would you rate it against the Undertaker’s other WrestleMania matches? Do you think the botched dive ruined the match? Did you think that HBK would break the Streak at the time? Which match between the two is your favourite and how do you think this compares to the follow-up bout? How are you celebrating the Undertaker’s debut this year, what are some of your favourite matches and moments of his? Whatever your thoughts, drop a comment below, go check out my other Undertaker match reviews, and donate to my Ko-Fi to suggest an Undertaker match you’d like me to cover.






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