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#1 The Undertaker & Shawn Michaels (2008)
HBK makes another appearance on this list 13 years after winning the Rumble from the #1 spot, Michaels would enter the match at #2. The man who entered first, none other than The Undertaker.
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There were many reasons why the first two entrants of the 2008 Royal Rumble was special. These two legends had not feuded in the WWE since the iconic Hell In A Cell Match in 1997, so the fact that they were going one-on-one to kick off the Rumble match, it was special.
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The other reason is that this was the moment that started the road to one of the greatest matches of all-time. After over a half an hour in the match, Michaels would eliminate The Undertaker.
Fast forward a year to 2009, and Michaels believed in his mind he could be the first person to defeat The Undertaker at WrestleMania. He defeated JBL for the right to face Taker, and the rest was history at WrestleMania XXV.
