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By: Aubrey Sitterson

At the 25th Anniversary of WrestleMania, Shawn Michaels will attempt to do something no other Superstar has been able to accomplish: Defeat Undertaker on The Grandest Stage of Them All, ending The Phenom's 16-0 winning streak. (Match preview)

HBK and The Deadman have both reached the pinnacle of their profession, earning the respect of the entire WWE Universe in the process. They are "Weapons of Fate," hardened ring warriors that were long ago set on an unavoidable collision course, making their historic WrestleMania match one that was destined to happen. Join WWE.com as we take a look back at the events that laid the groundwork for this heavily anticipated contest. 

Presented by the new video game, Wanted: Weapons of Fate, available March 24, 2009.

Reaching new heights

Though WrestleMania X wasn't Shawn Michaels' first time on The Grandest Stage of Them All, his Intercontinental Title Ladder Match against Razor Ramon was the contest that cemented HBK's place in WrestleMania history. Still recognized today as one of WWE's greatest matches, Michaels and Ramon set the bar high for every Ladder Match to follow, innovating such practices as suplexes from the top rung, dropkicks to a climbing opponent and even using the ladder itself as a weapon. Though HBK lost the match, he began to lay his claim on the title of "Mr. WrestleMania."
Photos | More | Watch

Iron Men

Shawn Michaels took part in another all-time classic match at WrestleMania XII, facing Bret Hart for "The Hit Man's" WWE Title in a 60-minute Iron Man Match. At the end of the grueling hour, neither Superstar had scored a pinfall, so Gorilla Monsoon ordered the match into overtime with sudden death stipulations. During that time, HBK hit Hart with Sweet Chin Music to get the pin and win his first WWE Championship. But Undertaker was no slouch that night either, scoring his sixth WrestleMania win over Michaels' former bodyguard, the massive Diesel.
Photos | Taker vs. Diesel
Iron Man Match: More | Watch

Entering the devil's playground

When Undertaker and Shawn Michaels face off at the 25th Anniversary of WrestleMania, it won't be for the first time. The two took part in the inaugural Hell in a Cell match back at Badd Blood: In Your House. Satan's Structure took its toll on the ring warriors, with the fight moving to the top of the cell and HBK falling to a table below. All that cold steel failed to prevent outside interference however, as Taker's brother Kane made his debut, attacking The Phenom and giving Michaels the opportunity to crawl onto his opponent and win this brutal match-up by pinfall.
Photos | More | Watch

Pyrrhic victory

Things weren't over for Shawn Michaels and Undertaker following HBK's Hell in a Cell win. Their rivalry spilled over into the 1998 Royal Rumble, where they competed in a Casket Match. Michaels fought valiantly against The Deadman, but in the midst of the match, The Showstopper landed awkwardly on the coffin, suffering a severe back injury that would eventually force him away from the ring for more than four years. Despite HBK's injuries, Taker has still never defeated him due to another appearance by Kane, who forced his brother into the casket, setting it ablaze.
Photos | More Casket Matches

Last (dead)man standing

Undertaker and Shawn Michaels butted heads once again at the Royal Rumble nearly a decade later in 2007. HBK was on fire, coming in and proceeding to eliminate four powerful Superstars including Edge and Randy Orton. But Michaels was at a distinct disadvantage when Undertaker entered the match last at No. 30. That didn't stop an exhausted HBK from taking the fight to The Deadman, however, hitting him with Sweet Chin Music. But in the end it was Undertaker who was victorious, earning the right to compete in the main event at WrestleMania 23.
Photos | More | Watch

Making history

WrestleMania XXIV saw both Superstars compete in historic matches. Undertaker had a World Heayweight Title match against Edge in which The Master Manipulator pulled out all the stops. Still, Undertaker prevailed, winning his second World Heavyweight Title. Meanwhile, Shawn Michaels took part in a match against his friend and mentor, Ric Flair, that would see The "Nature Boy" retire if he lost. In spite, or perhaps because of the love he had for Flair, HBK defeated 'Naitch, giving the Hall of Famer a tremendous match that was also his last.
Photos | Taker vs. Edge | Watch
Michaels vs. Ric Flair | Watch